In this episode, Michael Koenig speaks with Greg Keller, co-founder and CTO of JumpCloud, about identity access management and why it’s becoming one of the most important operational systems in the age of AI.

Greg explains how traditional identity systems were designed for office-based companies running Microsoft infrastructure and why that model broke as companies moved to SaaS, cloud infrastructure, and remote work.

The discussion then turns to the next big shift: the rise of AI agents and synthetic identities inside organizations.

As companies deploy more AI tools, the number of machine identities may soon outnumber human employees. Managing what those systems can access will become a critical security and operational challenge.
 

Topics Covered

What a CTO actually does

Greg explains the different types of CTO roles and how technology leaders help companies anticipate where the market is headed.

Identity Access Management explained simply

IAM answers three core questions inside every company:

Who are you?

What can you access?

How is that access managed?

Why the old IT model broke

Traditional identity systems were built for on-premise offices and Microsoft infrastructure. Modern companies now operate across:

SaaS applications

cloud infrastructure

remote work environments

multiple operating systems

How JumpCloud approaches identity

JumpCloud was built to manage identity across devices, applications, and infrastructure regardless of platform.

Where Okta fits in the ecosystem

Okta helped modernize browser-based authentication through Single Sign-On, while JumpCloud focuses on broader identity infrastructure.

AI, Security, and Synthetic Identities

Why COOs should push AI adoption

Greg argues AI adoption is no longer optional. Companies must encourage teams to improve productivity and efficiency using AI.

The rise of synthetic identities

AI agents, bots, APIs, and service accounts are becoming new actors inside companies that require identity governance.

Bots may soon outnumber employees

Organizations will soon manage more machine identities than human ones.

AI as a potential insider threat

AI systems can become security risks if they are granted excessive permissions or misinterpret policies.

The API key governance problem

Many AI integrations rely on API keys, which are often poorly managed and can create hidden security risks.

Key Takeaway

As companies adopt AI, identity access management becomes the control layer that determines what both humans and machines are allowed to do inside the organization.
The companies that manage identity well will move faster and operate more securely.

Links:

Michael on LinkedIn: https://linkedin.com/in/michael-koenig514

Greg on LinkedIn: https://www.linkedin.com/in/gregorykeller/

JumpCloud: https://jumpcloud.com/

Between Two COO’s: https://betweentwocoos.com

Episode Link: https://betweentwocoos.com/ai-agents-identity-access-greg-keller

Guest: Seth Levine

Book: Capital Evolution

Podcast: Between Two COOs

Host: Michael Koenig

What we cover

• Why Seth wrote Capital Evolution and why now
• Why today’s economic shift is structural, not cyclical
• How power has moved from public institutions to businesses
• What companies are being asked to carry that they weren’t built for
• How AI fits into this broader realignment
• Early signals that companies are adapting well to AI
• What strong executive teams do differently during uncertainty
• Common leadership traps when change happens too fast
• A real crisis from a portfolio company and what the executive team did well
• The new leadership muscle operators need for the next decade

Episode Chapters / Timestamps

00:00 – Introduction

01:40 – Seth’s 30-second pitch for Capital Evolution

04:05 – Why this shift is structural, not cyclical

07:20 – What’s broken in the current economic model

11:00 – The power shift from government to business

15:10 – What leaders are quietly losing

18:45 – Where AI fits into this realignment

23:30 – What boards see when AI adoption works

28:05 – How strong executive teams handle uncertainty

33:40 – Leadership traps during rapid change

38:10 – A crisis inside a portfolio company

44:00 – The new muscle operators must build

48:50 – A moment Seth never thought he’d see

00:00 — Cold open: “Something new is fucked up in my world every day”

02:00 — The Yoda t-shirt story + the mythology of Brad Feld

04:00 — “Give First” vs. “Pay it Forward”: philosophy, not obligation

07:00 — Why giving isn’t altruism — and how it works in complex systems

10:00 — Positive-sum vs. zero-sum: tennis, trust, and long games

13:00 — Does giving create outcomes, or just energy?

16:00 — Why Brad writes books: longform thinking as meaning-making

20:00 — Searching for meaning through mentorship and reflection

23:00 — “I hate the phrase pattern recognition” — mentorship done right

28:00 — The power dynamic between founders and mentors

32:00 — Management through commitment, not control

35:00 — Agile as an operating system for accountability

38:00 — Emotional intelligence and the role of executive coaches

41:00 — Mentor vs. coach vs. therapist vs. advisor

45:00 — Trust as the foundation of all high-leverage relationships

47:30 — Wild story: when the second floor of Sphero’s building collapsed

52:00 — “They can’t kill you and they can’t eat you” – Len Fassler’s advice

55:00 — Closing thoughts on being the Bill Murray of venture capital

We dissect how go-to-market organizations evolve from $20M to $100M ARR, the power of focus and role separation, and how to keep silos aligned around one customer story.

Peter also explains the shift from “payments orchestration” to “open payments” and how Spreedly’s position as the original player in the space gives them unique leverage. We walk through the future of agentic commerce, Google’s new agent-to-agent payments protocol, and what it means when agents can transact faster than any human could ever shop.

We close out with the Dodgeball acquisition, a primer on fraud orchestration, and a wild story about working an entire night shift at a nightclub during a meltdown launch.

Topics Covered:

• How Peter defines the journey to presidency
• The “right person, right problem” framework
• One-way vs two-way doors for staffing big problems
• How to scale a GTM org from $20M to $100M
• Why open payments replaces orchestration
• Spreedly’s unique market position and 15-year head start
• Agent to agent commerce and Google’s new payments protocol
• How AI changes the velocity of money movement
• Fraud orchestration and Spreedly’s acquisition of Dodgeball
• Balancing profitable growth vs growth at all costs
• Perception vs reality in leadership
• Peter’s wildest “I never thought I’d see that” story

This week on Between Two COOs, Michael sits down with Harris Clarke, COO at GuideCX, to talk about what steady leadership actually looks like inside fast-changing companies.

Harris started his career in protocol and operations for the U.S. Department of State, where “process” wasn’t just a buzzword — it was survival. He shares how those lessons translate to running a modern SaaS organization and why purpose, process, and payoff are the anchors of any good meeting.

They dig into:

• How government discipline shaped Harris’s operating style
• The “three P’s” framework for productive meetings
• Why decision speed is overrated — and what Harris means by “Did anyone die or go to jail?”
• What he learned from executive coaching and board feedback
• How GuideCX built a new product category around customer onboarding
• How AI is quietly reshaping how he manages teams and prepares communications
• Why calm is a competitive advantage during crisis moments like SVB

Michael also gives context at the top: this episode was recorded across two sessions, after a recording issue mid-interview (and yes, he’s now officially a Riverside convert).

It’s a conversation about building trust, running tight systems, and keeping your head when everything around you is changing.

Harris Clarke on LinkedIn
GuideCX

Michael Koenig on LinkedIn

Between Two COO's Website

Episode Website

In this episode of Between Two COOs, Michael sits down with Anna Elwood, COO of Cascade, the strategy-execution platform helping companies turn plans into results.

Anna shares how she evolved from Broadway actor to operator, scaling companies like Zocdoc, Knotel, and Teachable before joining Cascade to build the muscle of strategy execution.

She explains how to create an “operating rhythm” that keeps teams aligned across time zones, the tension between governance and red tape, and how Cascade helps leaders link vision to measurable execution.

The conversation dives deep into AI’s role in operations, the future of hybrid work, and what it takes to move from chaos to clarity in a global startup.

Anna’s storytelling — especially her account of leading through Superstorm Sandy — highlights what real-time operational leadership looks like when everything goes sideways.

Timestamps

00:00 – Intro & sponsor

01:00 – The chaos of Superstorm Sandy

02:00 – Anna’s journey: from theater to tech

06:00 – The making of a generalist

10:00 – Joining Cascade and fixing retention

11:00 – Creating a “working rhythm”

14:00 – Governance vs. red tape

17:00 – The 5 pillars of strategic maturity

19:00 – Turning strategy into execution

24:00 – How Cascade uses AI internally

28:00 – OKRs, KPIs, and strategy frameworks

33:00 – Who owns strategy?

36:00 – Rebuilding a business overnight

43:00 – Closing thoughts

Between Two COO's - https://betweentwocoos.com 

Episode Website - https://betweentwocoos.com/anna-elwood-coo-cascade

Anna Elwood on LinkedIn - https://www.linkedin.com/in/annaelwood

Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514 

Guest: Lance Willett, Chief Quality Officer at Automattic

Topics Covered:

• How Automattic’s open source culture evolved over 20 years
• What a Chief Quality Officer actually does—and why it matters
• Quality = Craft × Context, and how that feedback loop scales
• Automattic’s AI strategy: support bots, contextual UI, and site generation
• The importance of tools like Linear and Storybook in enforcing quality
• How Automattic balances speed, risk, and governance with AI experimentation
• Lessons from stabilizing Tumblr during its post-acquisition reboot
• Prioritization and the dangers of unbounded optimism
• Leadership takeaways from working closely with Matt Mullenweg

🕰️ Time Map

00:00 – 03:00: Intro and Lance’s journey from freelancer to Automattic

03:00 – 06:30: How Automattic’s open source ethos evolved over 20 years

06:30 – 10:30: What it means to be a Chief Quality Officer—Craft × Context

10:30 – 15:00: Scaling quality: repo sprawl, signal vs. noise, and auditing

15:00 – 20:00: UX details like forms, performance, and speed as quality levers

20:00 – 24:00: Driving culture change with standard tooling (Linear, Storybook)

24:00 – 28:00: Guardrails for AI experimentation and internal governance

28:00 – 32:00: AI at Automattic: support bots, contextual UI, AI site builder

32:00 – 36:00: Competing with Webflow, Wix, and Squarespace through innovation

36:00 – 38:30: Balancing ecosystem contribution with revenue and investor pressure

38:30 – 41:00: Lessons from stabilizing Tumblr: cost, culture, safety, turnover

41:00 – 44:00: Automattic’s long-term challenge: bounded optimism and focus

44:00 – 46:30: Leadership wisdom from Matt Mullenweg: details always matter

46:30 – 49:00: Lance’s $250K mistake—and what it taught him about leadership

https://brodo.com/ (our other sponsor 😂)

https://fullstackleader.blog/ (work topics: WordPress, tech, productivity, quality, & more)

https://lance.blog/ (fun stuff: poems, stories, links; photos “on the go”)

https://linear.app/

https://clay.earth/ via https://automattic.com/2025/06/12/automattic-welcomes-clay/

Companies with dedicated quality efforts:

https://anthonyhobday.com/blog/20240914.html

> While fixing small bugs might not 10x your growth overnight

> Not fixing them will make 10x growth impossible over time

Credit: Casey Winters – someone you should have on this show if you haven’t already

https://caseyaccidental.com/

Episode webpage - https://www.betweentwocoos.com/automattic-chief-quality-officer-lance-willett-wordpress

Michael Koenig - https://linkedin.com/in/michael-koenig514 

Between Two COO's - https://betweentwocoos.com 

Why Linda still codes on weekends — and what it teaches her about the future of AI (6:00)

How AI is changing what Webflow builds — and how fast they build it (3:30–13:00)

What happens when websites are no longer built just for humans (14:00)

The rise of AEO (Answer Engine Optimization) and what it means for ops (17:00–21:00)

Favorite LLMs and workflows — from Claude Sonnet to custom GPTs (23:00–26:00)

How Linda builds a culture of innovation — and why bad ideas are worth celebrating (29:00)

Leading through operational ambiguity and defining what to say “no” to (49:00)

How product thinking helps Linda prioritize and run the business (54:00)

Creating an actual in-office “innovation lab” — and what worked (1:04:00)

Wild story: how her team navigated the SVB collapse weekend (1:08:00)

In this episode, Doug and I cover:

• Why “AI agent” is more than just a buzzword
• The difference between deflection and resolution in AI-powered support
• How Kustomer structures RevOps, GTM, and forecasting
• What it means to operate with high-context vs. generic playbooks
• How Doug thinks about team structure, ownership, and cross-functional clarity
• Predictions for agent-to-agent communication: “Your AI agent will talk to my AI agent—and we’ll both just read the summary.”

Timestamps:

(02:00) Defining agentic AI in customer service

(06:30) From deflection to resolution: Kustomer’s AI in action

(10:15) How AI is changing the org chart and team design

(14:00) The problem with low-context playbooks

(17:45) RevOps structuring and ownership

(22:00) Forecasting: visibility vs. execution

(27:00) AI tooling, integration, and buyer psychology

(31:00) Agent-to-agent interactions and AI futurecasting

(34:30) What Doug’s watching next in ops and AI

Links

Doug Hanna on LinkedIn - https://www.linkedin.com/in/douglashanna1/

Kustomer - https://www.kustomer.com/

Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514

Between Two COO's - https://betweentwocoos.com 

Key Takeaways:

RevOps aligns and optimizes sales, marketing, and customer success, ensuring efficient and sustainable growth.

Effective RevOps requires balancing strategic planning, data-driven analytics, and tactical execution.

Successful RevOps integration hinges on clear communication, cultural alignment, and strategic hiring decisions.

AI is poised to significantly impact RevOps by improving efficiency, though human judgment remains crucial.

Metrics and KPIs in RevOps must directly correlate to revenue growth, profitability, and organizational efficiency.

Brad emphasizes proactive disruption, transparency, and alignment to navigate the rapid evolution of sales operations.

Timestamps:

(02:00) What is RevOps and how Brad transitioned into it from finance

(07:00) Common misconceptions and early mistakes in RevOps

(11:00) Building a robust RevOps foundation and data hygiene

(15:00) Creating alignment across sales, marketing, and customer success

(20:00) Key metrics and strategic decision-making in RevOps

(24:00) AI’s impact on RevOps and potential pitfalls

(30:00) Real-world experiences with AI-powered sales calls

(33:00) RevOps vs. SalesOps and defining terms clearly

(36:00) Advocating for RevOps budgets and demonstrating value

(40:00) Lessons learned about effective communication and internal alignment

Links:

90 Days Free of Fellow's AI Meeting Assistant: https://fellow.app/coo

Brad Rosen on LinkedIn: https://www.linkedin.com/in/bradrosen1/

Michael Koenig on LinkedIn: https://www.linkedin.com/in/michael-koenig514/  

Sales Assembly: https://www.salesassembly.com/

Between Two COO's: https://betweentwocoos.com 

Episode URL: https://www.betweentwocoos.com/sales-assembly-president-brad-rosen-on-unlocking-growth-and-why-revops-is-critical-for-sustainable-scaling 

Timestamps:

(02:00) Fellow’s shift from productivity tool to AI assistant.

(07:00) Implementing large-scale organizational change.

(13:00) Managing change and internal communications.

(20:00) Moving toward an agentic, automated workflow future.

(23:00) Unexpected real-world AI uses at Fellow.

(29:00) Privacy, security, and enterprise-grade compliance.

(33:00) Selecting and utilizing LLMs and managing AI economics.

(36:00) How to build an AI-first company from scratch.

(40:00) Why existing companies struggle to adopt AI effectively.

(44:00) Practical advice on starting AI implementation in established companies.

Key Takeaways:

Fellow transformed from a productivity tool into a strategic, AI-powered assistant helping organizations automate meetings, streamline workflows, and derive actionable insights.

Aydin emphasizes the necessity of disruptive innovation, detailing Fellow’s cultural shift toward agility and fearlessness to stay ahead in the AI-driven landscape.

Security, privacy, and compliance remain core to Fellow, with advanced governance and redaction features designed specifically for internal enterprise meetings.

Real-world AI applications include automatically generating meeting summaries, tracking and following up on action items, updating CRM and project management systems, and creating customized client communications.

Insights on successful AI adoption: Aydin highlights practical steps organizations should take, from establishing AI councils to experimenting actively with new technologies and leveraging external AI consultants.

Links

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo

Episode URL: https://betweentwocoos.com/the-bold-pivot-from-meetings-to-ai-with-aydin-mirzaee-ceo-of-fellow

Between Two COO's website: https://betweentwocoos.com 

Michael Koenig on LinkedIn: https://linkedin.com/in/michael-koenig514

Aydin Mirzaee on LinkedIn: https://www.linkedin.com/in/aydinmirzaee/

AI and Privacy: Navigating the EU's New AI Act with Flick Fisher

In this episode of Between Two COOs, host Michael Koenig welcomes back Flick Fisher, an expert on EU privacy law. They dive deep into the newly enacted EU Artificial Intelligence Act and its implications for businesses globally. They discuss compliance challenges, prohibited AI practices, and the potential geopolitical impact of AI regulation. For leaders and operators navigating AI in business, this episode provides crucial insights into managing AI technology within regulatory frameworks.

00:00 Introduction to Fellow and AI Meeting Assistant

01:01 Introduction to Between Two COOs Episode

02:08 What is the EU’s AI Act?

03:42 Prohibited AI Practices in the EU

07:46 Enforcement and Compliance Challenges

12:18 US vs EU: Regulatory Landscape

29:58 Impact on Companies and Consumers

31:55 Future of AI Regulation

Between Two COO's - https://betweentwocoos.com 

Between Two COO's Episode 

Michael Koenig on LinkedIn

Flick Fisher on LinkedIn

Flick on Data Privacy and GDPR on Between Two COO's

More on Flick's take of the EU's AI Act

[00:00] Introduction – Michael introduces Fellow as a trusted AI meeting assistant.
[01:00] Welcome to Between Two COOs – Introducing Justin Etkin and Tropic.io.
[02:00] The evolution of procurement – From cost-cutting to strategic value creation.
[05:00] When should companies start formalizing procurement?
[07:00] Common mistakes businesses make in procurement.
[10:00] Using data and AI to improve procurement efficiency.
[12:00] Negotiation strategies and dealing with vendors.
[16:00] The role of AI in procurement and automation potential.
[20:00] How companies are shifting towards integrated procurement platforms.
[23:00] The intersection of procurement and legal, finance, and security.
[28:00] Justin’s wildest COO experience – Painting walls before an office move-out.
[30:00] Closing thoughts – Where to follow Justin and learn more about Tropic.io.

Tropic - https://www.tropicapp.io/

Between Two COO's - https://betweentwocoos.com 

Episode URL - https://betweentwocoos.com/tropic-coo-justin-etkin

Michael Koenig - https://linkedin.com/in/michael-koenig514

Justin Etkin - https://www.linkedin.com/in/justintropic/

Don't forget to check out www.fellow.app/coo for a 90-day free trial of their AI Meeting Assistant.

Key Takeaways:

• Hidden C-Suite Job Market: The majority of C-level roles are filled through networking, talent partners, and executive recruiters before job postings are even considered.

• Role of Networking: Building strong relationships within your industry and maintaining top-of-mind positioning with decision-makers is crucial.

• Non-Traditional Candidates: Market shifts, such as the rise of AI and post-COVID changes, are creating opportunities for candidates from unconventional backgrounds.

• AI in Executive Recruiting: True Search uses AI-driven tools like Thrive to manage data at scale, identifying the best candidates more efficiently.

• Career Advice for COOs: Gaining hands-on experience in both value creation (product/tech) and value capture (go-to-market) functions can prepare COOs for CEO roles.

• Culture Fit: Evaluating culture fit involves assessing how a candidate aligns with and enhances the company’s existing culture without disrupting it.

• The Board Member Journey: To be considered for a board position, candidates need specialized expertise and experience managing boards or navigating complex organizational challenges.

Notable Quotes:

• “Position yourself within your network as someone ready to step into a C-level role—start those conversations early.”

• “If everyone’s a thought leader, no one is a thought leader. Focus your voice and expertise on what truly adds value.”

• “To be a successful CEO, you need to have hands-on experience in both product and go-to-market functions.”

Evan’s Unforgettable Moments:

• Two finalists in a CEO search accidentally meeting mid-interview process due to scheduling overlap—illustrating the small-world nature of the C-suite ecosystem.

• Delivering news to two candidates while they stood together on the sidelines of their kids’ soccer game, showing how interconnected the executive world can be.

Be sure to check out Fellow's AI Meeting Assistant and get 90 days free at fellow.app/coo.

In this episode of Between Two COOs, host Michael Koenig interviews Jon Mark, COO of Vestwell, a leading provider of digital platforms for workplace savings and investment programs. Vestwell supports nearly 25,000 small businesses, over a million savers, and $25 billion in assets under management across all 50 states.

They discuss Vestwell’s mission to close the savings gap, its innovative approach to financial wellness, and Jon’s career journey from Bridgewater to COO at Vestwell.

Key Topics Covered

1. Vestwell’s Vision and Product Offerings

• Simplifying workplace savings through innovative digital platforms.

• Expanding beyond 401(k)s to include student debt paydown, 529 education savings, and more.

• Recent acquisition of Gratifi from Morgan Stanley to help employers support student loan repayment.

2. The Retirement Crisis

• Addressing the lack of sufficient retirement savings in the U.S.

• The role of state-sponsored retirement programs and employer-provided plans.

• Larry Fink’s warning about the coming retirement flood.

3. AI in Financial Wellness

• Vestwell’s integration of AI to enhance user experiences, including a new AI chatbot.

• Using AI to simplify complex financial concepts and empower financial advisors.

4. Jon Mark’s Career Path

• Transition from VP of Strategy to COO at Vestwell.

• Mentorship, curiosity, and deep problem-solving as key drivers of career progression.

• Lessons learned from working at Bridgewater and applying them to operations at Vestwell.

5. Navigating Risk and Strategy

• Managing risk by tying decisions to money, time, and outcomes.

• Balancing mission and growth by focusing on small and medium-sized businesses.

• Using a “chassis” approach to consolidate financial tools for broader impact.

6. Operational Challenges in a Regulated Industry

• Overcoming complex regulatory requirements.

• How Vestwell builds scalable, efficient processes within strict constraints.

7. The Role of the COO

• A COO’s need to handle diverse domains—engineering, HR, healthcare, and more.

• Strategies for managing imposter syndrome and fostering collaboration.

• Building a transparent culture through metrics and regular communication.

8. Mission-Driven Decision Making

• How Vestwell aligns its strategy with its mission to close the savings gap.

• Clear objectives, OKRs, and open communication as tools to drive alignment.

Memorable Moments

• Jon’s story about solving three major operational issues in one night before an acquisition deal closed.

• Insights on how Vestwell is innovating in financial wellness while maintaining a mission-oriented approach.
 

Key Quotes

• “You can’t just approach problems with jargon—you need to deeply understand the substance.”

• “Having a tangible North Star is critical. For us, it’s funded accounts—it’s the metric that matters most.”

• “At the end of the day, strategy and tactics are just bets with different time horizons.”

About the Host

Michael Koenig is the host of Between Two COOs, a podcast that dives into the stories, strategies, and advice of today’s top Chief Operating Officers. Learn more at betweentwocoos.com.

00:00 Introduction to Between Two COOs

00:16 Valentin Gruber's Background and Home2Go Overview

01:01 Home2Go's Market Position and Public Listing

01:57 Home2Go's Business Model Evolution

05:16 Scale and Transactions at Home2Go

07:19 Subsidiaries and Acquisitions

15:36 Strategic Planning and Problem Solving

22:39 Leadership and Company Culture

24:20 Management Approach and Decision-Making Techniques

25:45 Balancing Learning and Expertise

28:59 The Importance of Pre-Reads in Decision Making

32:41 Leaders Staying Connected to Problems

33:54 Understanding SPACs and HomeToGo's Public Journey

38:20 Strategic Use of SPAC Funds

39:18 Evaluating and Executing M&A Deals

42:05 Memorable Moments and Financial Discipline

46:26 Conclusion and Farewell

In this episode of Between Two COOs, host Michael Koenig interviews Stacey Ryan, the COO of School of Rock - a global music school franchise. Stacey debunks a common misconception about the business's origin, noting it predated and inspired the 2003 film. She discusses the operational challenges of managing a global franchise, particularly through the COVID-19 pandemic, and highlights the innovative pivot to remote lessons and live-streamed shows. Stacey also delves into her role in founding Frontwoman.org, aimed at empowering women in leadership roles across various industries. The discussion covers her career trajectory, the importance of mentorship, operational strategies for scaling, and the significant impact of maintaining a supportive and innovative culture for both students and franchisees.

00:00 Welcome to Between Two COOs: Meet Stacey Ryan

00:28 The Real School of Rock: Beyond the Movie

00:52 Empowering Women Leaders: The Mission of Frontwoman.org

02:10 Navigating Challenges: Pandemic Response and Innovation at School of Rock

12:49 Operational Insights: Building a Global Music Education Empire

25:21 Empowering the Next Generation: Talent Assessment and Retention

31:25 Frontwoman.org: Championing Women's Leadership and Empowerment

40:40 Closing Thoughts and Resources

This episode delves into the complexities and potential inefficiencies of meetings in the professional world, emphasizing the staggering number of unproductive meetings held daily. Highlighting the innovative approach of Shopify in canceling recurring meetings to save significant time, the conversation introduces Fellow, a SaaS product aimed at optimizing meeting structures, agendas, and action items to enhance management processes. Aidan Mizrahi, the CEO of Fellow, shares his journey from being unaware of structured management processes to creating a platform that serves as a manager's co-pilot, focusing on the intricacies of managing differently for every team member and adapting over time. Furthermore, Mizrahi discusses the pivotal role of asynchronous meetings in remote work, the significance of setting meeting norms, and leveraging AI to improve efficiency and decision-making in organizations. The episode also explores the balance between security and innovation when integrating AI into business processes and concludes with Mizrahi sharing a personal anecdote on how AI has become a part of his daily routine for brainstorming and learning.

00:00 The Meeting Epidemic: Unveiling the Problem

00:58 Introducing Fellow: The SaaS Revolutionizing Meetings

01:42 A Deep Dive into Fellow's Origin and Mission

01:50 From Startup to Acquisition: A Journey of Learning and Growth

05:14 The Power of Structured Management Processes

09:43 Implementing Effective Meetings at Scale with Fellow

15:51 Optimizing Meetings for Action and Accountability

20:00 Redefining Meeting Culture: Strategies for Efficiency

29:06 Embracing Remote Work: The Future of Meetings

32:37 Unlocking the Power of Asynchronous Meetings

33:43 The Value of Time and Asynchronous Work

35:18 Inside the Operations of Fellow: Mastering Efficiency

35:44 The Art of Meeting Types and Decision Making

40:21 Leveraging AI for Business Efficiency and Innovation

45:58 Navigating AI Ethics and Security in Business

48:34 AI Presentations: Sharing Knowledge and Inspiring Innovation

56:03 The Impact of Super Managers Podcast on Leadership

01:02:07 Exploring New Frontiers with AI: A Personal Experiment

01:04:41 Connecting with the Community and Wrapping Up

(00:12) Advice for CEOs and COOs

This chapter welcomes Cameron Harold, the founder of COO Alliance and author of "The Second In Command," as we celebrate the release of his new book and examine its content, which serves as a guide for both CEOs and COOs. We explore Cameron's transition from COO to CEO, the mindset shifts that accompanied this change, and his insights into the balance between work and life. Cameron shares his experiences and lessons learned from running a business at a young age, including the importance of delegating, saying no, and focusing on the most critical tasks. The discussion also touches on how the book has already impacted the COO Alliance and the value it provides in understanding the CEO-COO dynamic.

(12:37) Promoting From Within vs. Hiring Externally

This chapter we explore the importance of creating a culture of continuous improvement within companies, akin to the mindset of elite athletes or performers. I share an anecdote about Patrick Roy to illustrate the resilience and determination that we aim to instill in our teams. We discuss strategies for fostering a safe environment where feedback is welcomed and viewed as a tool for growth, emphasizing that it's the systems, not individuals, that often need adjustment. We also touch on the sentimental value of sports heroes, as I recount a personal encounter with my childhood idol, Ken Dryden. Finally, I address the considerations involved in deciding whether to promote from within or hire externally for leadership roles, factoring in the individual's ability to complement the CEO's skills, their leadership qualities, and the strategic implications of such decisions, especially in companies with specialized knowledge or intellectual property.

(17:24) Flexibility in Organizational Structure With AI

This chapter examines the importance of flexibility in business operations and leadership. We explore the concept of a "bobbin' weave culture" where being too rigid can be detrimental, and the benefits of flowing like water, taking the path of least resistance towards the company's vivid vision. I discuss the necessity for leaders to align with core values and purposes, akin to a bobsled track, to guide the organization's journey. Additionally, we look at the challenges of introducing flexibility into rigid structures, using the example of Gerber Auto Collision's approach to acquisitions and the philosophy of "selling, not telling" to integrate new teams. The chapter also highlights the power of positive reinforcement and personal praise in leadership, drawing lessons from Howard Behar's practice of handwritten thank you notes at Starbucks, emphasizing the value of gratitude and recognition in driving employee success and satisfaction.

(24:55) Exploring AI Tools and Admired COOs

This chapter, we explore the significance of AI in the modern workplace, highlighting how our employees and CO Alliance members are encouraged to experiment with AI tools for one to two hours each week. We discuss the vast array of available AI applications, far beyond the widely mentioned ChatGPT, and the benefits of sharing experiences with these tools among teams to build momentum and enhance productivity. Examples include the transformative effects of AI on podcast production, such as using Descript to edit speech or Podium Stage for content creation. Additionally, we touch upon the importance of adaptability, illustrated by historical shifts in technology within NASA, and wrap up with admiration for influential COOs like Cheryl Sandberg and Matt Rawlings, noting how they exemplify effective leadership and innovation.

(30:39) Leadership Lessons and Insights

This chapter explores the contrasting leadership styles and trajectories of two COOs of 1-800-Got-Junk, with a focus on the impact of Eric Church's internal-facing, process- and people-centered approach as he grew the company from $70 million to $450 million, in stark contrast to my own media-facing, brand-building style during a different company growth phase. We also discuss the critical lesson of listening to team members, exemplified by a near-bankruptcy experience, and share a personal strategy for becoming a better listener by physically sitting on one's hands to encourage attentiveness. Finally, we examine the importance of asking systemic rather than symptomatic questions within leadership, illustrated by an anecdote involving Starbucks and the significance of maintaining operational systems for company-wide consistency.

(37:02) Catch Up and Discuss Book Promotion

This chapter celebrates the successful collaboration between CEOs and COOs as we unpack the critical dynamics of their partnership. I extend my gratitude to Cameron for sharing his insights and congratulate him on his new book, "Second in Command," a must-read for current and aspiring COOs, as well as CEOs seeking to hire their right-hand executive. We reflect on the nuances of the CEO-COO relationship and the importance of understanding each other's roles to foster a productive working environment. The discussion emphasizes the book's relevance for those looking to enhance their leadership teams and the overall health of their organizations. Thank you, Cameron, for joining me and enriching our listeners with your expertise.

Links:

Second In Command book - https://www.amazon.com/Second-Command-Unleash-Power-Your/dp/1544537603

COO Alliance - https://cooalliance.com/

Cameron Herold on LinkedIn - https://www.linkedin.com/in/cameronherold/

Unique Ability by Dan Sullivan - https://uniqueability.com/

Situational Leadership - https://en.wikipedia.org/wiki/Situational_leadership_theory

Fellow.app - https://fellow.app/coo/

Episode on Between Two COO's - https://betweentwocoos.com/41

Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514/

Join us as we explore not only the definitions and distinctions within the AI Act but also its everyday implications for business operations, from HR decisions to the product safety landscape. With generative AI technologies like ChatGPT on the rise, understanding the nuances of this legislative framework has never been more crucial. We'll navigate the potential new compliance roles the Act may create and predict whether this regulatory move could become the global gold standard. Tune in for a comprehensive analysis that will equip COOs and business leaders with the foresight needed to thrive in an AI-governed future.

(00:06) EU AI Act and Its Impact

(11:50) Regulations and Definitions of AI

(27:38) The Implications of the AI Act

Links

Episode link: https://www.betweentwocoos.com/the-eu-vs-ai-the-legal-opinion-with-flick-fisher-partner-at-fieldfisher/

Flick's previous episode on GDPR: https://www.betweentwocoos.com/data-privacy-gdpr-flick-fisher/

Flick on LinkedIn: https://www.linkedin.com/in/felicityfisher/

Fieldfisher: https://www.fieldfisher.com/

Between Two COO's: https://www.betweentwocoos.com/

Michael Koenig on LinkedIn: https://linkedin.com/in/michael-koenig514/

As the startup ecosystem continues to evolve, we dissect the influence of continuous learning on company culture, inspired by industry pioneers. I open up about the enriching experience of partnering with product and engineering-driven founders and how passion plays a decisive role in a startup's trajectory. We consider how startups like Productboard are innovating in operations and product management with the use of AI, highlighting the agility required to manage rapid change and the ethical considerations of handling customer data.

In our conversation, we delve into the challenges of scaling up to the enterprise market and the importance of building a culture that can gracefully manage internal friction points. I share my approach to fostering empathy and collaboration across departments, revealing personal anecdotes and strategies for aligning diverse perspectives within a company. Tune in for a rich discussion full of practical insights, memorable moments, and tips for nurturing a successful startup environment. Follow Productboard on LinkedIn and check out their blog for more engaging content that can help steer your company towards growth and innovation.

(00:06) Saying Yes to New Opportunities

(08:14) Startups' Impact on Learning Culture

(17:25) AI for Operations and Product Management

(31:34) Navigating Enterprise Market Challenges and Feedback

(37:07) Friction and Empathy in Customer Relations

(45:25) Developing Empathy and Cross-Departmental Collaboration

Links

Greg Strickland on LinkedIn: https://www.linkedin.com/in/gregstrickland/

Episode Link: https://www.betweentwocoos.com/productboard-coo-greg-strickland

Matt Blumberg: https://startupceo.com/

The Hard Things About Hard Things by Ben Horowitz: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205

Amp It Up by Frank Slootman: https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115/

Radical Candor by Kim Scott: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375

Michael Koenig on LinkedIn: https://www.linkedin.com/in/michael-koenig514/

(04:36 - 06:03) Peer to Peer Tour Guide Platform

(07:27 - 09:26) Learning and Customer Obsession Importance

(12:35 - 13:56) Creativity and Execution in Strategy

(16:11 - 17:06) Identifying Core Values for Company Culture

(21:48 - 23:03) Accelerating Digitization and the QR Code

(36:32 - 37:43) Investment Strategy and Flywheel Approach

(39:48 - 40:47) International Tensions and Investment Impacts

(43:17 - 44:43) Applying AGI and AI to Operations

(00:11) The Travel Experience Industry Journey

This chapter welcomes Tao, COO of GetYourGuide, to share insights into the burgeoning travel experience industry. I explore how GetYourGuide, a company that started in a dorm room, grew into a $2 billion enterprise, selling over 80 million tickets to travelers seeking unique experiences, such as private tours of the Vatican Museum. We look at the travel experience market as an untapped online frontier, previously dominated by offline transactions and now worth $300 billion. Tao recounts the founding story of GetYourGuide, from its original concept as a peer-to-peer platform for tour guides to pivoting towards professional activity operators, marking the beginning of its success. We also touch upon the company's recent $194 million funding round and discuss the increasing trend of travelers preferring experiences over material possessions.

(13:56) Adapting Culture and Surviving Crisis

This chapter begins by exploring the integration of culture with changing strategies, emphasizing the importance of a consistent culture that supports shifts without causing disruption. I discuss the development of authentic core values by sharing a story of initial failure and eventual success through a reflective process with the leadership team, highlighting the key role of core values in determining who fits within a company. The conversation then pivots to the impact of COVID-19, recounting the immediate challenges and strategic decisions made in response to the pandemic, including the choice not to lay off staff and to continue investing in the future. The chapter concludes with an optimistic outlook, noting a strong recovery and promising prospects for the years following the initial crisis.

(21:10) Travel Industry

This chapter focuses on how businesses adapted during the pandemic, particularly addressing the balance between long-term planning and immediate operational needs. We touch on innovative measures like salary sacrifices for stock options and government-subsidized work hour reductions. We highlight the insights gained from having co-founders with molecular biology backgrounds, which helped us stay ahead in understanding the virus's impact on the travel industry. Additionally, we discuss the acceleration of digitization due to the pandemic, using the QR code's newfound ubiquity as a prime example. This digital shift significantly impacted operations, especially for our partnerships with historical attractions and museums, which had to quickly adapt to digital ticketing and queue management. Lastly, we examine the surge in travel as restrictions lifted, debunking the idea that the spike was merely 'revenge tourism' and noting the persistent trend towards domestic tourism.

(31:53) Board Members, Funding, Global Network Effects

This chapter focuses on the strategy behind assembling a board of directors for a private company, highlighting the importance of selecting members who bring expertise and accountability. We explore the company's recent Series F funding round, which includes a mix of cash and a revolving credit facility, designed to provide financial flexibility. The significance of raising funds during a period when many tech companies struggle is discussed, emphasizing the company's steady growth and prudent financial practices that have led to a successful up-round without resorting to complex financial instruments. I share insights into the deployment of the raised capital, underlining the company's investment into a technology-driven flywheel model, which encompasses building customer audience, enhancing the product, and acquiring a diverse inventory to support their mission of expansion, particularly in the U.S. market.

(40:48) Travel and AGI Building Connections

This chapter begins with reflections on the value of a connected world and the peace dividend concept, emphasizing how less military spending can boost investment in other sectors like technology and education. I examine the impact of decoupling on trade efficiency and express hope for the role of travel in fostering empathy and cultural understanding. I share insights on the potential of AGI and chat GPT to transform operations in various fields, including machine learning, translation, customer service, and personalized recommendations. I highlight the impressive capabilities of AI in instant translation, which can facilitate global communication and commerce. Lastly, I recount the startling experience of near-zero revenue during COVID-19 and discuss how resilience led to recovery. To keep up with these themes, I encourage listeners to use GetYourGuide for their travels and connect with me, Tao Tao, on LinkedIn.

Links: 

Playing to Win: How Strategy Really Works

The Mind of the Strategist

Amazon's Leadership Principles

Netflix's Core Values

Delivering Happiness 

Turning on the Lights at the Vatican

GetYourGuide

Episode URL

Michael Koenig on LinkedIn

COO Alan Christensen shares his journey and Duist's success without institutional investment, pioneering remote work and dividing responsibilities with CEO.

(11:48) Future of Remote Work and Communication

Remote work's significance in shaping the future, utilizing asynchronous communication, transparency, and documentation for effective management.

(22:28) Recruitment, Career Growth, and Feedback Processes

Hiring, company culture, flat hierarchy, career development, and professional growth are emphasized by the speaker.

(31:04) Challenges With Trademarks and Feedback

Remote company Todoist's values, challenges, hands-on management, stable squads, feedback framework, and trademark infringement case.

(06:56 - 08:05) Tech and Memory Retrieval

(11:40 - 12:51) Chat GPT and Data Privacy Integration

(17:34 - 18:44) Leveraging AI for Company Augmentation

(22:34 - 23:47) AI for Efficiency and Exceptional Hiring

(30:31 - 31:01) Pivoting to Capture Meeting Data

(38:38 - 39:00) COO and Chief of Staff Collaboration

(43:27 - 44:27) Using Cultural Values as a Guide

(47:10 - 48:20) Accountability and Candor in Successful Teams

(55:58 - 57:01) Impressions of AI Summarization

---

(00:11) Augmenting Human Memory With AI

This chapter of Between Two COOs features a conversation with Dan Sroker, co-founder and CEO of Rewind, a personalized AI tool that augments human memory. Host Michael Kanag explores the inspiration behind Rewind and how it can give users a "superpower" by making all their digital interactions searchable and AI-able. They also discuss the importance of memory and how technology can enhance our natural capabilities. The conversation touches on the potential impact of relying on AI for memory recall and draws parallels to the evolution of phone numbers. Overall, this chapter explores the fascinating intersection of technology and human memory.

(12:51) The Future of AI in Operations

This chapter explores the potential impact of AI on future operations. Our guest, who has experience in scaling a company using AI, discusses how AI can be a powerful tool for leveraging human capabilities and increasing productivity. We also touch on the importance of privacy and security in AI, highlighting how companies that do not embrace it may struggle to compete in the future. The conversation concludes with a discussion on the role of AI in remote work and the potential for smaller teams to achieve more with the help of technology.

(18:44) Enhancing Productivity With Artificial Intelligence

This chapter explores the impact of AI on workplace productivity and efficiency. We discuss the release of GPT-4 and its potential to speed up tasks and increase productivity. Privacy challenges and the importance of employee awareness are also addressed. We examine how AI can bridge the gap between ambiguity and tasks, using Rewind's email summarization feature as an example. The significance of hiring exceptional senior staff and maintaining focus to achieve more with less is emphasized. Lastly, we touch on the potential impact of AI on the job market for recent graduates.

(27:19) The Impact of STEM on Technology

This chapter emphasizes the significance of STEM education in fostering creativity and problem-solving skills through technology. Our guest shares their personal journey with robotics, which led to the creation of innovative products like Optimize-A and Mac. The discussion also highlights the role of M1 and M2 chips in their company's pivot and how it enables local data privacy. Ultimately, we are reminded of the transformative potential of technology and the importance of adapting and maximizing its benefits.

(38:29) COOs and Chiefs of Staff

This chapter explores the dynamics of having a COO and chief of staff simultaneously, and how this partnership can benefit a company. We discuss the importance of screening for a good COO and chief of staff, as well as their role in creating a positive work environment. The former CEO shares his experience of achieving the number one spot for best place to work and the role of psychological safety in creating a fantastic workplace. Overall, this chapter provides valuable insights into the importance of a strong partnership between a CEO and their COO and chief of staff, and how it can contribute to the success of a company.

(42:23) Cultural Values in a Company

This chapter emphasizes the importance of defining and living up to company values. The host, who has experience at Google and now runs his own company, shares insights on creating a strong company culture by clearly defining values and behaviors that align with them. He highlights the need for these values to be a living document, constantly evolving and being used as a basis for performance management. The conversation also touches on the potential pitfalls of using values as a marketing tactic rather than a genuine reflection of the company's beliefs. Overall, this chapter highlights the role of company values in creating a positive and successful work environment.

(45:58) Psychological Safety in Leadership Importance

This chapter explores the importance of psychological safety in creating a successful and cohesive team. We discuss the guest's experience with psychological safety in their previous company and how they are implementing it in their current venture. We emphasize the need for a shared language and vernacular around psychological safety to create a sense of safety within a team. The guest also shares their regrets about not maintaining a balance of comfort and accountability in their previous company as they grew. We highlight the importance of a long-term orientation and hiring slowly to maintain a strong culture. The chapter concludes with the guest discussing their vision for their current venture and their determination to make it their life's work.

(52:03) Ask the Right Question and Succeed

This chapter explores the importance of conducting effective reference checks during the hiring process. We discuss the significance of asking the right questions and building rapport with references to obtain honest and valuable feedback on potential candidates. Additionally, we touch on the game-changing role of AI in the hiring process. The chapter concludes with a discussion on how to handle unexpected moments that may arise in the workplace.

(06:15) Community Solar and Renewable Energy Innovation

(15:37) Data Platform and Energy Transformation

(24:21) Acquisitions, Integration, and Board Composition

(29:05) Startup Board Management and Risk Balancing

(35:51) Leadership, Growth Mindset, and Overcoming Challenges

(42:18) Connecting Through Cold Emails

(00:12) Clean Tech and Disrupting Energy Market

We discuss Energy 101 today with Kate Hemington, co-founder and COO of Arcadia Power. Kate has a degree from the University of Oxford and a background in corporate litigation, making her well-equipped to tackle the energy industry. We talk about energy being a regulated monopoly, the trillions of dollars in the market, and how Arcadia is bringing digitization opportunities. We also discuss the unique perspective of having a legal and policy background and how it allowed them to get into the market and innovate. Kieran and Kate bring their own experience with energy policy and law, respectively, to the conversation.

(06:15) Community Solar and Renewable Energy Innovation

We enter the complex world of community solar. She explains how the state incentivizes third party developers to build renewable power sources and how Arcadia simplifies the process by giving customers a guaranteed savings rate. We understand how electricity works and why community solar is a guaranteed win for the customer, as well as how it’s helping to displace dirty electrons with clean ones.

(15:37) Data Platform and Energy Transformation

We chat about the potential of retrofitting four billion machines to achieve maximum decarbonization. We explore how the market has shifted in the last 15 years, with over 90% of new electrons produced in the US being renewable. We also discuss how Arcadia's data platform, Arc, is providing other companies with data, such as EV manufacturers and solar developers, to help their customers with micro decisions. Finally, we consider how Arcadia is managing its mission and culture with its switch to serving enterprises.

(24:21) Acquisitions, Integration, and Board Composition

We discuss acquisitions and product integration. We explore the importance of growth and expansion, and how to know when an acquisition is right. We examine the challenges of integrating products, the risks of taking on too much too soon, and the importance of understanding a company and its culture before making an acquisition. We also look at the value of an independent board member, and the importance of having a plan when it comes to acquisitions.

(29:05) Startup Board Management and Risk Balancing

We explore risk management and cash management. Kate shares how they've become better at board management, and how to let board members know what you need from them. We discuss how macroeconomic events have led to a guard your flank mentality, but how regulated line of revenue has given them a floor. We also talk about how the energy transition is a larger market than the macroeconomic events and how it has helped them to be aggressive in a down environment. Finally, Kate shares her thoughts on tight times and how it has created a renewed focus.

(35:51) Leadership, Growth Mindset, and Overcoming Challenges

We explore the importance of understanding growth mindset and being comfortable with discomfort. We also look at the importance of communication in building a successful team and how to effectively manage people. Kate shares her experience of bringing a global operations team together and the challenges of leading a co-founder. Finally, we look at the moment of surprise when the team received five cease and desist letters from utilities and how they overcame the challenge.

(42:18) Connecting Through Cold Emails

The power of cold emails. We emphasize the importance of making connections, and provide advice on how to maximize reaching out to potential contacts. Tap into the power of cold emails and take the opportunity to make meaningful connections. Don't forget to subscribe to Between Two COOs and leave us a review on Apple Podcasts to share your thoughts and help spread the word.

Kate on LinkedIn: https://www.linkedin.com/in/kate-henningsen/

Episode: https://betweentwocoos.com/arcadia-power-coo-kate-hennigsen

Arcadia Power: https://www.arcadia.com/

Michael Koenig on LinkedIn: https://www.linkedin.com/in/michael-koenig514

(0:00:12) - Remote Company Operations and Knowledge Management

Daren explains the importance of low context communication, compounding interest, and over communicating for successful remote teams.

(0:08:59) - Embracing Remote Work as Operating Model

Daren Murph and I discuss operations of successful remote companies, process definition, documentation, culture, macroeconomic downturn, investing in operations, and using history as a guide.

(0:20:22) - Knowledge Management and Generative AI

We examine knowledge management, Generative AI data sets, and remote onboarding for successful companies.

(0:25:52) - Remote Onboarding's Impact on Engagement

Remote work success is achieved through discipline, connection, and a balanced work-life ratio.

(0:41:25) - Engaging Town Hall Strategies and Perspectives

Darren shares advice on effective remote work, from town halls to partnering with business leaders, to keep pushing forward.

Beyond product explanation, we venture into the world of remote hackathons and the operational challenges within. Nitin highlights anticipating potential issues within a remote team and the significance of aligning all-hands meetings with the organization's structure. More so, we explore Prisma's unique take on transparency and collaboration as they open-source their processes.

Finally, we delve into the less conventional aspects of managing a remote company. Nitin shares insights on why they hired a trained psychologist for HR and how it helps prevent employee burnout. He also unveils an interesting balance between commercializing open-source projects and maintaining a vibrant community through the 123 framework. Additionally, we discuss operational execution, aligning teams to KPIs, and Nitin’s unique approach to quarterly planning. This episode is a must-listen for tech enthusiasts and remote team managers looking for practical tips and fascinating insights.

(0:00:13) - Explaining Prisma and Building Knowledge Sharing

Nitin Gupta explains Prisma to his mother, Prisma University educates internally, and technical team members share knowledge.

(0:11:13) - Remote Hackathon and Organizational Structure Management

Nitin Gupta discusses hackathon operationalization, remote team issues, all hands meetings, organization structure, and open sourcing processes.

(0:18:40) - Psychologists and Open Source in Remote Companies

Nitin Gupta emphasizes HR with psychologist hire, uses 123 framework to balance open source project and community vibrancy.

(0:35:30) - Operational Execution and Alignment of KPIs

Nitin Gupta discusses aligning teams to KPIs, concentrating on company-wide objectives, quarterly planning, and negotiating with a mobile handset manufacturer.

Episode link: https://betweentwocoos.com/prisma-coo-nitin-gupta

Nitin Gupta: https://www.linkedin.com/in/gniting

Michael Koenig: https://www.linkedin.com/in/michael-koenig514/

In this chat, we also explore the potential of generative AI to increase speed, accuracy, scalability, complexity, and accessibility of structured language, and how ZenBusiness leverages this to expand capacity. From discussing the importance of data protection to understanding the potential threats to businesses, Shanaz provides a comprehensive overview of the operations side of the company, including their customer support in the contact center.

Shanaz also talks about the company’s organizational structure, with CTO, HR, customer success, legal, program management, procurement, and corporate citizenship all reporting to her. Learn about the process of hiring great people, and how her passion and love for what she does is the key to success. She also shares her experiences with M&A, and how she and her team at HomeAway used the strategy of acquiring existing vacation rental services to make the company global. From tracking the macroeconomic environment to discussing the advantages of remote working, Shanaz provides a wealth of information for anyone interested in understanding the workings of a successful business.

Listen in as we explore the application of generative AI in streamlining contract renewals and procurement with Munish. Our conversation uncovers how AI can automate the procurement process and enhance workflow, shedding light on how Productiv's product can help educate everyone involved in the software buying process. We then discuss Munish's journey to his COO role and how his previous experience at LinkedIn influenced his approach to building a software company. We also consider the challenges of selling a product that doesn't contribute to top-line revenue and discuss the objective of creating a platform that helps people be more Productiv in their roles.

Munish also shares his experience with crisis management and decision-making, emphasizing the importance of communication and risk management during turbulent times. He offers a glimpse into his method of gathering data from other founders and investors to make informed decisions. This conversation provides valuable insights into how to approach decision-making when faced with an imperfect amount of information. This episode is packed with wisdom and strategies for managing SaaS applications, making it a must-listen for anyone navigating the modern software landscape.

--------- EPISODE CHAPTERS WITH SHORT KEY POINTS ---------

(0:00:13) - SaaS Governance and Optimization Importance

Munish Gandhi discusses SaaS portfolio governance, rationalizing SaaS spend, streamlining SaaS procurement, and SaaS underutilization.

(0:14:57) - Streamlining Contract Renewals and Procurement

Munish Gandhi and I discussed how AI can streamline contract renewal, automate procurement, and improve workflow with Productiv's Apricot Meta.

(0:22:28) - Path to COO Role and Corporate Lessons

Munish Gandhi shares his journey to COO, his experience at LinkedIn, and tactics to make LinkedIn for Sales.

(0:33:02) - Crisis Management and Decision Making

Munish Gandhi emphasizes communication, risk management, data gathering, and informed decision-making in times of crisis.

Links

Munish Gandhi on LinkedIn - https://www.linkedin.com/in/munishgandhi/

Productiv - https://productiv.com

Episode URL - https://betweentwocoos.com/productiv-coo-munish-gandhi

Between Two COO's - https://betweentwocoos.com 

Michael Koenig - https://linkedin.com/in/michael-koenig514

Join us as we sit down with Allen Narcisse, former COO at Workrise and co-founder and CEO of Gigs, for an enlightening conversation about his journey in the gig economy. Allen takes us through his career trajectory, starting from his initial venture, eBuyLine, to his stints building Uber and Lyft, and finally, to his current venture, Gigs. Listen in as Allen shares valuable insights on building marketplaces, the importance of a great first impression, and the inspiration behind Gigs.

In the second part of our discussion, we explore the intricacies of operating a gig economy platform. Allen shares the three-step process Gigs uses to source jobs and engage job seekers and the crucial role of having a team with previous founders, Lyft, and Uber DNA. He also shares his perspective on prioritization and ensuring the team has the resources and talent to accomplish winning moves.

In the final part of our conversation, we discuss the future of the labor market in the face of automation and AI. Allen shares his thoughts on the need for job seekers to be equipped with the right information and tools to navigate the changing job market. Tune in to hear more about Gigs’ business model, the cost per application model, and how it ensures employers only pay for qualified applicants. Finally, we touch on the implications of automation on the labor force and the need for better communication between employers and workers.

Links:
Gigs - https://getgigs.co/

Allen Narcisse - https://www.linkedin.com/in/allen-narcisse/

Michael Koenig -https://www.linkedin.com/in/michael-koenig514/

Episode URL - https://betweentwocoos.com/gigs-ceo-allen-narcisse

Between Two COO's - https://betweentwocoos.com 

--------- EPISODE CHAPTERS WITH SHORT KEY POINTS ---------

(0:00:12) - Building the Gig Economy

Alan discussed founding eBuyLine, Uber/Lyft, Workrise, and Gigs, and the importance of making a great first impression in the job placement sector.

(0:08:48) - Gigs CEO Discusses Approach and Operations

Alan discussed Gigs' three-step process, the importance of team DNA, prioritizing and providing resources and talent.

(0:16:01) - Forming the DNA of a Company

Allen Narcisse and I discussed customer focus, courageous conversations, scaling information, psychological safety, and everyone's opportunity to weigh in.

(0:25:11) - Ownership and Coaching for Great Company

Hiring ambitious people, setting mutual expectations, weaving values into decisions, allowing mistakes, and coaching rather than filling gaps are discussed.

(0:33:21) - Empowering Job Seekers, Addressing Automation

Allen Narcisse and I discussed Gigs' business model, job seekers' empowerment, cost per application, automation's implications, and employer-worker communication.

Together, we explored the intricate operations of creating a successful indoor urban farm, from engineering and construction to farming and distribution processes. Tobias shared fascinating insights on how Square Roots uses cutting-edge technology to minimize its environmental impact, reduce its carbon footprint, and produce food sustainably despite the challenges posed by climate change.

We also touched upon the importance of staying true to a company's mission and values, as well as how Square Roots navigated the COVID-19 pandemic and adapted their business to continue providing fresh, nutritious, and mouth-watering produce to their community. Don't miss this thought-provoking conversation on the future of urban agriculture and how it can help us tackle some of the most pressing global issues of our time.

In This Episode

(0:00:16) - Indoor Urban Farming for Sustainable Food

• Tobias  and I discuss engineering, construction, farming, tech operations, packing, and distribution of urban food production.

(0:10:55) - Revolutionizing Urban Farming With Square Roots

• Tobias discusses Square Roots' sustainable farming process, commercialization, and chefs' satisfaction.

(0:25:29) - Reducing Carbon Footprint for Local Farming

• Tobias and his team use technology to produce food sustainably, reducing their environmental impact through design, energy, and distribution.

(0:31:02) - Mission, Values, and Adapting to Change

• Tobias and I discuss mission and values, adapting to unexpected circumstances, and physical operations to stay focused.

Links

Square Roots - https://www.squarerootsgrow.com

Tobias Peggs - https://www.linkedin.com/in/tobiaspeggs

Michael Koenig - https://linkedin.com/in/michael-koenig514

Episode - https://betweentwocoos.com/square-roots-ceo-tobias-peggs

With a humanitarian-drive and strong business acumen, Stephan’s career in the COO seat began at Cotopaxi, following the sale of his company, Kembrel in 2013. During this time, Stephan reconnected with an old University of Pennsylvania Wharton and Lauder Institute classmate, Davis Smith, with the commitment to build a brand for those who shared their values: a deep-rooted interest in giving back and a passion for the outdoors. From there, came Cotopaxi, an outdoors brand, which has never wavered from its ESG principles and humanitarian focus. Under Stephan’s stewardship, Cotopaxi has become a role model for how businesses can achieve the seemingly at-odds goals of making the world a better place while achieving growth. As a B-Corp using environmentally friendly sourced materials and ethically-sourced labor, Cotopaxi’s values and colorful apparel have struck a chord with its customers, generating $100m in revenue, aiding 1.5 million people in poverty, and assisting 90k refugees throughout South America in 2021 alone.

Where to find Stephan: 

• Linkedin

Mentioned on the episode:

• Davis Smith, Cotopaxi’s Co-founder & CEO
• Brad Hiranaga, Cotopaxi’s Chief Brand Officer, General Mills’ former Chief Marketing Officer
• Damien Huang, Cotopaxi’s President and incoming CEO,  Eddie Bauer’s former CEO
• Grace Zuncic, Cotopaxi’s Chief Impact Officer, Chobani’s former Chief People Officer
• B Lab
• Ego is the Enemy

A biz ops wizard, Woody’s career started as a Business Analyst at McKinsey in 2006, focused on M&A and private equity due diligence. With a passion for creating joyful customer experiences, Woody jumped to the gaming and entertainment website IGN, leading corporate strategy before attending Stanford University’s Graduate School of Business, where he was amongst the top students, earning him distinction as a Siebel Scholar. 

Following a short stint at Disney as a Global Development Associate for Imagineering, Woody joined Lyft in February 2013 as employee 34. Initially tasked with leading Lyft’s launch in Los Angeles, just the company’s second market, Woody mastered these rollouts, becoming the company’s VP of Global Operations in September 2017. 

Before departing in September 2019, he helped grow the company from $100k to $3 billion in annual revenue. He led hallmark company growth events such as 24 launches in 24 hours and launching in New York with only two weeks’ notice. 

After six years with the company, Woody embarked on a new challenge: summitting Mount Everest! Returning to the business world as the President & Head of Product at TeamSnap in March 2020, Woody led the sports app company to double its revenue and its first profitable quarter. Approached with the opportunity to lead a micro-mobility company through its next phase, Woody recently joined Lime in January 2022. With rumors of a Lime IPO following its first profitable year, Woody’s vast expertise and experience have him well-prepared for the work the company has cut out for him. 

Where to find Woody: 

• Linkedin

Now amongst the top InfoSec legal experts, Flick’s journey in the space began when she moved to the Bay Area in 2015. Initially joining her firm, Osborne Clark’s, Palo Alto office to focus on transactions in the tech industry, her move coincided with the emerging push for increased data privacy regulations. In January 2016, Flick moved to Fieldfisher as an Associate and the fourth employee of its newly formed Privacy, Security, and Information Group, immersing herself in all data privacy matters, with a particular interest in EU compliance as the GDPR was implemented. Since then, Flick has become a Partner, stepping into a de facto COO role, and overseeing the firm's day-to-day operations. 

Where to find Flick: 

• LinkedIn

As mentioned on the episode:

• Mark Webber, Fieldfisher’s US Managing Partner, Technology & Data
• Max Schrems - Austrian lawyer & digital privacy activist
• Fieldfisher’s Privacy Blog
• European Data Protection Board

With an entrepreneurial spirit that emerged during his childhood in Germany, Holger’s journey has been guided by his unsatiated love of building things from the ground up. Leaning further into this spirit in college, Holger founded a successful student consultancy with several friends. Upon graduating in 2010, Holger joined T-Mobile, working in the Division of the CEO. 

While he valued his experience and time working close to leadership, the hunger to build his own company drew him to join his college friends in Berlin. Recognizing that they lacked the time they once had as college students to quickly read books in full, Holger and his team founded Blinkist in 2012. 

Founded to make knowledge quick and accessible through short summaries of books, Blinkist was quickly able to capitalize on emerging consumer preference for shorter and mobile-accessible content to become the preeminent company in the space. Taking full advantage of being the first mover, Blinkist has expanded beyond written book summaries to audio and podcast summaries and has grown its user base to over 21 million across the globe while securing $40 million in venture funding. 

Where to find Holger: 

• Linkedin
• Twitter

Mentioned on the episode:

• Paul Graham, venture capitalist
• Markus Witte, Founder & CEO of Babbel
• Elliot Darvick, Head of Regional Marketplace at Workrise
• Nathaniel Manning, Co-founder & COO of Kettle
• Patrick Lencioni, business author
  • The Advantage: Why Organizational Health Trumps Everything Else in Business
  • The Five Dysfunctions of a Team: A Leadership Fable
  • The Ideal Team Player: How to Recognize and Cultivate the Three Essential Virtues

A citizen of the globe, having spent time living in several countries outside his home country of Bolivia, Diego has expertise across various departments, ranging from operations to marketing to commercial strategy. Starting his career in the quick service restaurant (QSR) industry upon returning to South America after college in the US, Diego served as the Operations Manager for McDonald’s Columbia. He led day-to-day operations for the company’s McOpCo chain from 2003 to 2005. After a brief stint as Burger King’s Director of Operations for the Dominican Republic, Diego shifted his attention to the telecommunications industry, starting his journey in the space as the Vice President of Sales for Trilogy/Viva Dominicana in 2007. In 2009, Diego joined Swedish telco giant Millicom as the Head of Sales & Marketing for its Tigo brand, rising to the role of CEO of its Rwanda market in 2011. Following a successful tenure as the CEO of Tigo/Millicom’s Senegal business, Diego headed further east in March 2017, signing on as Vodafone Qatar’s Consumer Business Unit Director before taking the reins as its COO in March 2018. 

Where to find Diego: 

• LinkedIn
• Twitter

Cameron is a growth expert and an acclaimed “CEO Whisperer”, who has led several companies, focusing on people and process improvement. In 2000, Cameron was brought aboard as the COO of 1-800-GOT-JUNK?, leading operations, P&L, franchise development, and sales amongst other responsibilities. He helped grow 1-800-GOT-JUNK? from 12 franchises and $2 million in revenue to 300 franchises across 4 countries and $150 million in revenue when he departed in 2007. Since then, he’s written 5 books and serves as an independent consultant for several major companies. Upon realizing there was no group for COOs to learn and share their knowledge, Cameron founded the COO Alliance in 2016 as a network for COOs to exchange ideas and best practices. 

Where to find Cameron: 

• CameronHerold.com
• COO Alliance
• Second in Command Podcast
• Instagram
• Facebook
• LinkedIn
• YouTube

Cathy is a strategic people leader, with an exceptional track record of laying the foundation for strong company cultures. After several years in the UK as a social services counselor, Cathy returned to the US as a human resources director. With her experience in the UK informing her people-centric approach to human resources, Cathy served as the Sr. Director of Human Resources at Epsilon for several years before joining Return Path as its Sr. People Director in 2008. 

Rising through the ranks to become the company’s Chief People Officer, Cathy fostered a strong partnership with Matt Blumberg, Return Path’s CEO, which was instrumental in helping the company build a development-focused culture. After departing Return Path in June 2019, Cathy teamed back up with Matt in 2020 to found Bolster, an executive talent marketplace, and to co-author Startup CXO: A Field Guide to Scaling Up Your Company's Critical Functions and Teams. 

In addition to her role at Bolster, Cathy serves as a Founding Board Member of Path Forward, a nonprofit organization dedicated to empowering people to return to the workforce after taking time off to care for a loved one.

Where to find Cathy: 

• LinkedIn
• Bolster

Mentioned on the episode: 

• Matt Blumberg, former CEO of Return Path, co-founder of Bolster, & author of Startup CxO: A Field Guide to Scaling Up Your Business
• Fred Wilson, co-founder of Union Square Ventures
• The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter by Michael D. Hawkins

Goodworld helps companies grow by making it easy to embed Social Impact into commerce, workplace culture and sustainability initiatives. Through our Social Impact experiences, sales teams close more deals at higher prices, HR teams increase employee engagement and attract talent, ESG teams drive ROI from their activities, and marketing teams create irresistible brands that boost product prices.

Dale Pfeifer is passionate about Social Impact, CSR and ESG. Dale is the founder and CEO of fintech Goodworld - named one of the World’s Most Innovative Companies and a World Changing Idea by Fast Company magazine. Their Social Impact Platform empowers employees, customers and communities to drive positive cultural change together through giving, volunteering and rewards.

Goodworld - https://goodworldnow.com

Dale Pfeifer's Ted Talk - Creating a good world one # at a time 

Dale Pfeifer on LinkedIn - https://www.linkedin.com/in/dale-pfeifer

Episode Webpage - https://betweentwocoos.com/goodworld-ceo-dale-pfeifer

Between Two COO's - https://betweentwocoos.com 

Lean Startup - http://theleanstartup.com

Michael Koenig on LinkedIn - https://linkedin.com/in/mkoenig514

Bolster: https://bolster.com/

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 

Episode webpage: https://betweentwocoos.com/jenny-lawton

Between Two COO's: https://betweentwocoos.com 

Handshake’s mission is to democratize access to opportunity: to help every student find the right job, no matter where they’re from or who they know.

Today, Handshake is the number one site for college students to find jobs. Handshake powers career offices at 1,300+ higher ed institutions—including 100+ community and technical colleges. With 550,000+ employers recruiting on Handshake—from every Fortune 500 company to nonprofits, startups, and more—schools that join Handshake see on average a 3x increase in the size and diversity of their employer network.

Jonathan Stull on LinkedIn: https://www.linkedin.com/in/jonstull/

Handshake: https://joinhandshake.com/

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514/

Between Two COO's: https://betweentwocoos.com/

Episode Site: https://betweentwocoos.com/handshake-coo-jonathan-stull/

Cyrus Mistry on LinkedIn: https://www.linkedin.com/in/cmistry

GoGuardian: https://www.goguardian.com

Episode Website: htps://betweentwocoos.com/gogaurdian-coo-cyrus-mistry

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514

Art Harding on LinkedIn: https://linkedin.com/in/arharding

People.ai: https://people.ai

Episode Website: https://betweentwocoos.com/peopleai-coo-art-harding

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 

Prior to Uplight, Angela was Chief Strategy Officer at Symantec, Chief Revenue Officer and Chief Marketing Officer at Rally Software, and Chief Executive Officer at Apto, so she's a clear underachiever. :)

Uplight is a technology partner for energy providers and the clean energy ecosystem to help them reach their decarbonization goals.  Uplight was last valued at $1.5 billion dollars, which is an achievement in and of itself, let alone for a company that's only 3 years old.

Episode Website: https://betweentwocoos.com/uplight-coo-angela-tucci/

Angela Tucci on LinkedIn: https://www.linkedin.com/in/angelatucci/

Uplight: https://uplight.com/

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 

The 80/80 Marriage: https://www.8080marriage.com/

Hotjar, is a European headquartered start-up with over 200 fully remote team members distributed across the globe. Ken is also a digital nomad and has been traveling with his family across Central America, Europe, and Africa for nearly 7 years.

Prior to his travels, Ken held leadership positions in traditional corporate environments where he gained great experience but was tied to his desk. He relishes life “outside the cube”.

Ken on LinkedIn: https://www.linkedin.com/in/kenweary/

Hotjar: https://www.hotjar.com/

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 

Steve Taylor on LinkedIn: https://www.linkedin.com/in/stephen-h-taylor/

HipTrain: https://hiptrain.com

Episode Webpage: https://betweentwocoos.com/hiptrain-coo-steve-taylor/

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 

ExecThread: https://execthread.com

Joe Meyer: https://www.linkedin.com/in/joejmeyer/

Michael Koenig: https://linkedin.com/in/mkoenig514/

Nathaniel has a long career of founding and leading companies including Fellow Robots, BRCK, the largest provider of public wifi in Africa, and Ushahidi the world’s largest open-source platform for crisis response. Along the way, he worked on furthering clean energy as part of the Clinton Climate Initiative at the Clinton Foundation, and Nathaniel was part of the Obama Administration's first class of Presidential Innovation Fellow where he was special advisor on open data at USAID, the world's premier international development agency, where he went on to become the Chief Data Officer.

With that kind of track record, it’s safe to say that Nathaniel puts his money where his mouth is when it comes to creating technological solutions to some of the world’s biggest problems.

Nathaniel on LinkedIn: https://www.linkedin.com/in/nathanielmanning/

Kettle: https://ourkettle.com/

Episode Website: https://betweentwocoos.com/kettle-coo-nathaniel-manning

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 

Prior to co-founding Hatch, Dave was the CTO of BabyCenter, where he was responsible for software engineering and product. 

Dave Weiss on LinkedIn: https://www.linkedin.com/in/daveweiss99

Hatch: https://www.hatch.co

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 

Episode website: https://betweentwocoos.com/hatch-coo-dave-weiss

Valerie kicked off her career in the early days of the internet with one software exit followed by one agency exit, in the Web 1.0 days. She gained a ton of experience across brand building and performance marketing, as well as e-commerce, in 15 years working in digital agencies in various roles including VP Operations, GM, VP Client Services.

Most recently she served as the Global Chief Digital Officer for the world’s foremost luxury conglomerate, LVMH, across 16 beauty brands. LVMH Beauty brands include a mix of iconic centuries-old luxury household names such as Parfums Christian Dior, powerhouses like Benefit Cosmetics, Givenchy, and Fresh, as well as more recently incubated hot businesses such as Fenty Beauty.

She’s recently returned to her startup roots at Dia & Co, where she has been the COO for the last 6 months. Dia & Co is the leading online multi-brand clothing retailer serving women who wear sizes 10 - 32. Dia & Co offers a membership service where stylists curate monthly boxes to help customers find their style, as well as a fast-growing marketplace where customers can shop direct for the very best brands offering inclusive sizing.

Valerie Hoecke on LinkedIn: https://www.linkedin.com/in/hoecke/

Dia&Co: https://www.dia.com/

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514

Part two, coming next month, focuses on scaling the go-to-market and creating $B's in value.

Shippo is a shipping software company backed by Bessemer and D1, where she led Marketing, Sales, Business Development, Customer Success, Customer Support, People Ops, and Strategic Planning. During her time at the company, Shippo's revenue grew 3x faster than the US eCommerce shipping market, and the company's valuation grew from $220M to over $1B in just 18 months.

Prior to joining Shippo, Catherine was the Chief Business Officer at Automattic, the company behind WordPress.com, during the company’s growth from a valuation of $1B to $3B. While at the company, she led the acquisition and integration of WooCommerce. Previously at Facebook, she helped launch the Facebook Audience Network and led the three-year planning process, and at Random House, worked on the transition from physical to digital books. Catherine began her career as a strategy consultant at McKinsey.

Stay up to date with Catherine at:

• LinkedIn: https://www.linkedin.com/in/catherine-stewart-800b841/
• Website: https://catherinetaylorstewart.com
• Episode Webpage: https://www.betweentwocoos.com/catherine-stewart-part-one-people

Stay up to date with Michael at:  https://linkedin.com/in/mkoenig514

Part 1 of Doug's session dropped on January 4th, 2022 and focuses on Doug's path to COO and scaling people and culture.

Part 1: https://www.betweentwocoos.com/part-1-grafana-labs-coo-doug-hanna/

Grafana Labs: https://grafana.com

Doug Hanna on LinkedIn: https://www.linkedin.com/in/douglashanna1

Episode Website: https://betweentwocoos.com/part-2-grafana-labs-coo-doug-hanna

Episode Transcript: https://betweentwocoos.com/part-2-grafana-labs-coo-doug-hanna/#transcript

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514

Michael Koenig on Twitter: https://twitter.com/mkoenig

Part 2 of Doug's episode will air in a few weeks and focuses on scaling the go-to-market.

Grafana Labs - https://grafana.com

Doug Hanna on LinkedIn: https://www.linkedin.com/in/douglashanna1

Episode Website: https://betweentwocoos.com/part-1-grafana-labs-coo-doug-hanna

Episode Transcript: https://betweentwocoos.com/part-1-grafana-labs-coo-doug-hanna/#transcript

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514

Michael Koenig on Twitter: https://twitter.com/mkoenig

Fred Wilson's post on working multiple jobs: https://avc.com/2021/10/working-multiple-jobs/

Founder Collective: foundercollective.com

Micah Rosenbloom on Twitter: https://twitter.com/micahjay1
Micah Rosenbloom on LinkedIn: https://www.linkedin.com/in/micah-rosenbloom-a0350/

Eric Paley: https://twitter.com/epaley/
Raj De Datta: https://twitter.com/rdedatta
Scott Belsky: https://twitter.com/scottbelsky
Bill Tranchard: https://twitter.com/btrenchard
Chris Dixon: https://twitter.com/cdixon
James Tamplin: https://twitter.com/jamestamplin
Dave Frankel: https://twitter.com/dafrankel

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 

Michael Koenig on Twitter: https://twitter.com/mkoenig

Nira.com 

Marie Prokopets on Twitter: https://twitter.com/MarieProkopets

Marie Prokopets on LinkedIn: https://www.linkedin.com/in/marieprokopets

Hiten Shah on Twitter: https://twitter.com/hnshah

Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 

Episode website: https://betweentwocoos.com/nira-coo-marie-prokopets

Transcript: https://betweentwocoos.com/nira-coo-marie-prokopets/#transcript

Justin focuses on building the next generation of consumer products, particularly where AI meets customer experience. Prior to Tucows, Justin was Head of Product & CX Innovation at Verizon. He founded Focus Health, Grey Seven Labs, and Qstir. He was a Director of Strategy and Experience at Macquarium, lead the Strategy and Innovation team at Arke Systems. He currently advises a number of startups focused on the next generation of AI platforms and products.

Justin Reilly on LinkedIn: http://www.linkedin.com/in/justinreilly

Justin Reilly on Twitter: https://twitter.com/justinMreilly

Justin Reilly on the web: https://justinmreilly.com

Tucows: https://tucows

Ting Fiber: https://ting.com/internet

Episode Webpage - https://betweentwocoos.com/justin-relly-tucows-chief-product-officer

Episode Transcript - https://betweentwocoos.com/justin-relly-tucows-chief-product-officer#transcript

Michael Koenig - https://linkedin.com/in/mkoenig514

True Ventures is a venture capital firm with an astonishing track record of investing in the best companies like Peleton, Fitbit, Ring, Duo Security, Automattic, and Sweetgreen, which just went public on the New York Stock Exchange.

Jim initially joined True Ventures as CFO in 2012 and now leads all operations as the firm's COO. He brings substantial operational and financial experience to venture-backed tech and biotech companies. Jim has held numerous operating and CFO positions, leading four companies through their IPO processes. When he is not focused on operations, he's doing all sorts of high-octane activities like racing his Yamaha R6 motorcycle.

Ben Horowitz's Book, The Hard Thing About Hard Things - https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205

True Ventures - https://trueventures.com

Jim Stewart - https://www.linkedin.com/in/james-stewart-b1b10320/

Episode Webpage - https://betweentwocoos.com/jim-stewart-true-ventures-coo 

Episode Transcript - https://betweentwocoos.com/jim-stewart-true-ventures-coo /#transcript

Michael Koenig - https://linkedin.com/in/mkoenig514

Check out:

Allie Fleder on LinkedIn: https://www.linkedin.com/in/allie-fleder

SimplyWise: https://simplywise.com

EUROUT: https://www.euroutconference.org

Episode website: https://www.betweentwocoos.com/allie-fleder-simplywise-eurout

Between Two COO's: https://www.linkedin.com/company/betweentwocoos

Michael Koenig: https://linkedin.com/in/mkoenig514

Running Remote: https://runningremote.com

Running Remote 30% Coupon Code: betweentwocoos

For a transcript of the episode, go to: betweentwocoos.com/allie-fleder-simplywise-eurout

• How a philosophy degree prepared him for everything and nothing at the same time
• Credit Suisse's attempt to crush the humanity out of him
• Creating security, safety, and certainty for employees
• Over-communicating without stressing people out
• How processes can improve people
• Getting rid of the office and going fully remote
• And lemurs. Yes, lemurs, the animals.

Chopra Global: https://chopra.com

Chopra Global's Brand New Mobile App: https://chopra.com/app

Chopra Global's Upcoming Events: https://chopra.com/retreats

Rich Wallach on LinkedIn: https://www.linkedin.com/in/wallachr

Episode website: https://www.betweentwocoos.com/deepak-chopra-global-coo-rich-wallach

Between Two COO's: https://www.linkedin.com/company/betweentwocoos

Michael Koenig: https://linkedin.com/in/mkoenig514

Running Remote: https://runningremote.com

Running Remote 30% Coupon Code: betweentwocoos

Michael Koenig: https://linkedin.com/in/mkoenig514