In-House

The state of legal technology and the future of legal practice

jon@caspianstudios.com (Docusign) — Wed, 18 Feb 2026 10:00:00 +0000

The legal industry is currently reeling from what markets are calling the "SaaSpocalypse." On January 30, 2026, Anthropic released its Claude CoWork platform with open-source legal plugins. This wasn't just another product launch; it wiped nearly $285 billion off software and legal tech stocks in a single session. Heavyweights like Thomson Reuters (TR), RELX, and LegalZoom saw double-digit crashes as the market realized that the "middlemen"—companies that simply provide AI-powered contract review—might be getting disintermediated by the LLM providers themselves.

Today, we’ll be talking with Zach Posner, Co-Founder and Managing Partner at The LegalTech Fund, about what this means for legal technology companies, the future of legal practice, and predictions from two experts on this topic for the next year.

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Unlocking Your Legal Career: Personal Branding, Community, and The Contract Nerds-Docusign Acquisition

jon@caspianstudios.com (Docusign) — Tue, 6 Jan 2026 20:27:14 +0000

Jessica and Hemma of DocuSign speak with Nada Alnajafi, founder of Contract Nerds. They all emphasize how important community is to building support and connections in the legal world. Nada shares the origin story of Contract Nerds and the impact that online platforms had on scaling her business.

The three also discuss the acquisition of Contract Nerds by DocuSign and the value of community-driven insights for product development.

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Key Quotes:

HEMMA: People don't like the networking word, but really just enjoying the community is enough. You don't need to need anything. What I find is being generous yourself, coming to the community with a service mentality, offering to help people when you can. You're not doing that conditionally. You're not looking for something in return. But boy, does it pay dividends sometimes.

NADA: It all starts with relationships and having a community allows people to come congregate in a platform, in a place, around a certain topic that they're all interested in. To build relationships and you never know what a relationship can do for you beyond just the genuine part of having that relationship where five years from now, it could lead to an acquisition. It could lead to a new job like it did for you, Hemma. It could lead to a speaking opportunity. It could lead to you winning that negotiation when otherwise you might have been stuck and showing up for the community and for the people in your life. Just genuinely without having those expectations or trying to steer it in a direction. But just come and be yourself. And give to others what you know, your knowledge, your experiences, and share. And that's how we build trust and that's how we build relationships.

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Time stamps:

05:20 - Meet our guest

18:20 - Selling Contract Nerds

21:35 - Building a presence in compliance

33:00 - Learning from your community

38:48 - Keep or Redline

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Links:

Find Nada Alnajafi on LinkedIn

Find Jessica Nguyen on LinkedIn

Find Dr. Hemma Lomax on LinkedIn
More about Docusign

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Navigating Liability and AI in Contracts

jon@caspianstudios.com (Docusign) — Wed, 10 Dec 2025 06:00:00 +0000

Jessica and Natalia of DocuSign interview Laura Belmont, General Counsel at Civis Analytics. They discuss the complexities of commercial contracts, as well as data breaches, liability, indemnification, and how AI is impacting legal agreements.

Laura describes defining and negotiating data breach clauses, standardizing security terms, and the risks posed by AI tools.

As GC of Civis Analytics, Laura helps businesses thrive while bringing data-driven truth to organizational decision-making–for some of the world's biggest companies and the world's largest social causes

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Time stamps:

02:22 - Meet our co-host Natalia

03:57 - Meet our guest Laura

06:13 - Facing litigation costs

08:46 - Negotiating data breaches

13:49 - Indemnification and liability today

20:23 - AI agreements

28:25 - Getting around negotiated CAPs

35:00 - Cross-functional collaboration

41:00 - Keep or redline?

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Links:

Find Laura Belmont on LinkedIn

Find Jessica Nguyen on LinkedIn

Find Natalia Jhaveri on LinkedIn
More about Docusign

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The Reporting Line: Does Your GC's Boss Really Matter?

jon@caspianstudios.com (Docusign) — Tue, 30 Sep 2025 14:23:42 +0000

Jessica, Jim and Victoria Harvey, Chief Legal Officer at Smile Brands, Inc., dive into the complexities of reporting structures for General Counsels (GCs), discussing the pros and cons of reporting to CEOs versus CFOs, and the broader impacts on a legal department's influence within an organization.

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Key Quotes:

Once when you're reporting to the CEO, you're setting the tone that you're also a strategic partner. You're bringing more to the table, and you're not just a compliance officer, although that is also part of my function. But you are there to help drive the business. You are part of the executive team. You're making the decisions to grow the business.

You always have to stay humble. And I can tell you, even though I've been with the company for a long period of time, whenever we have a new executive joining or someone else on my team joining, I'm always open to new ideas. Just because you've been doingcertain things a certain way, you need different perspectives. I think in your career, no matter what level you get to, you always have to be humble and respectful and listen to others' perspectives because your way may not be the only way to be doing something.

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Time stamps:

04:30 - Victoria’s journey

06:07 - Topic of the day

20:13 - Tactics for gaining influence

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Links:

Find Victoria Harvey on LinkedIn

Find Jessica Nguyen on LinkedIn

Find Jim Shaugnessy on LinkedIn
More about Docusign

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How AI disrupts the law firm model

jon@caspianstudios.com (Docusign) — Wed, 27 Aug 2025 08:00:00 +0000

Ken, Jessica, and Jenny Hamilton, CLO of Exterro, discuss AI’s potential in the legal profession. They dive into their favorite tools and how to apply them, as well as the importance of human oversight to ensure accuracy and compliance. Jenny also shares strategies for driving adoption within her team and making sure new tech meets the needs of her team.

Tune in to hear personal experiences, practical insights, and expert opinions on AI’s transformative potential and its challenges in legal.

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Time stamps:

02:20 - About Ken

03:49 - About Jenny and Exterro

05:05 - What’s exciting, what’s scary about AI?

09:28 - Helpful tools

17:58 - Driving adoption

23:23 - How to be a new adopter

26:18 - Advice for entry level associates

37:39 - How AI disrupts the law firm model

46:25 - Keep or redline

49:46 - Final takeaways

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Links:

Find Jenny Hamilton on LinkedIn

Find Jessica Nguyen on LinkedIn

Find Ken Priore on LinkedIn
More about Docusign

Subscribe on Apple Podcasts

Subscribe on Spotify

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Future-Proofing your Legal Department

jon@caspianstudios.com (Docusign) — Wed, 30 Jul 2025 10:00:00 +0000

Sandy MacDonnell, Head of Legal Ops at DocuSign, and Krysta Johnson, Senior Legal Ops Evangelist at DocuSign, highlight the importance of metrics, data, and AI in transforming the legal profession from cost center to strategic, growth-oriented role. Sandy and Krysta both stress the need for adaptability at a time of rapid tech changes, as well as best practices for implementing new legal technologies.

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Key Quotes:

SANDY: I think this is true about the rest of the industry as well, is that, you know, it's really seeing legal and putting legal in that more strategic kind of role and being that partner to the business, and being that department of yes and like, how does the legal team help our sales team sell more, not just tell them how they can't do things. So I think that's been a really fun evolution of, of the legal operations function. Um, and I'm just excited because I think it's opening up a lot of career opportunities for folks who've been in these types of roles. It's much more creative, much more kind of fun and, like forward looking, I guess I would say.

SANDY: I think if there's anything I've learned in legal operations, it's like things change all the time, right? You had like one thing you were running towards and the next day the GCs like, Hey, actually I wanna go chase this other thing. Being flexible, being, uh, adaptable, continuously learning, right?

Like in this world today that we're living in with ai, we're seeing, you know, like the legal landscape always changed quickly when I think about technology. But today it's changing so much more rapidly. So if you have some, you know, if you're hiring someone to do legal operations for you, that person better be super excited about change, about, you know, learning the new technologies, what's coming down the line, how are we gonna reshape our department to, to adopt those new technologies. Just so essential.

KRYSTA: We operate currently in most of the corporate world, in these very, somewhat isolated silos. Yes, there's some cross-functional collaboration, but I think the idea of these silos is what really kind of stifles a lot of change that could move a lot faster.

And I think we're going to see more centralized operations functions where there might be a, like dedicated people that support legal operations, but they will sit in a more dedicated operations function under say, the COO versus sitting within the legal team. As you said, Sandy, like there is a lot of democratizing of technology and like ability to educate yourself.

And I think just like we've seen changes in the past 20 years in the legal, like the legal field itself, we, we'll see that change in operations as well where you, you don't have people doing a lot of the more menial work.

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Links:

Find Sandy MacDonnell on LinkedIn

Find Krysta Johnson on Linkedin

Find Jessica Nguyen on LinkedIn

Find Ken Priore on LinkedIn
More about Docusign

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Reinventing Your Legal Career

jon@caspianstudios.com (Docusign) — Wed, 14 May 2025 10:00:00 +0000

Todd Smithline, CEO of Bonterms, describes the importance of developing skills that go beyond your legal expertise. Salesmanship, project management, and information synthesis all lend themselves to adaptability in both legal and non-legal roles. He describes the value of feedback, how to offer value to your clients, and how to stay positive.

Bonterms is the two-sided negotiation platform built on Standard Agreements. We solve contracts for Procurement and Sales, while keeping Legal happy. Average negotiation times on the Bonterms Platform are measured in minutes. Bonterms is lawyer-led and funded by XYZ Capital and Wilson Sonsini.

Key Quotes:

“ So I learned how to create a brand, how to create a product. Because even as lawyers, we are selling a product. I learned how to price a product, how to market a product, how to get a customer. How do you get a recurring customer? … I made the full step, the crazy step, the completely off the pier and into the bay step of stopping being a lawyer altogether. But even after that last leap, I took all my friends with me. I created this committee of 100 lawyers. I had a relationship with my prior firm. I was able to leverage the next step.”

“The one piece of advice I think I'd give lawyers who are interested in doing this: Sometimes I see this thing on LinkedIn where people say "Recovering lawyer" or "Former lawyer" or something like that. And I think I read that differently maybe than it's intended because I read it as them distancing themselves from that expertise and that experience. Whereas I think one of the easiest ways to make this move as a lawyer is to build on it, right? I think that all three of us did that, right? We didn't desert our former expertise, our relationships. We used them to spring to the next thing.”

“ I think the highest prized skill right now, across companies, is the people who can synthesize disparate information. And communicate it well, but at the same time deal with complex situations and nuance. This is something a lot of lawyers are trained to do. One of the skills that we really develop with lawyers is concentration. Paying attention to the details, pulling together disparate facts, and synthesizing information. So I think that is really going to be the coin of the realm going forward.”

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Time stamps:

01:12 - Meet David Wang

03:27 - Meet Todd Smithline

10:25 - Taking the leap away from legal

18:02 - Ensuring success in any role

27:47 - Non-legal roles to pursue

34:29 - How to approach law school

54:32 - Defining your value

55:52 - Keep or redline

57:45 - Where to find Todd

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Links:

Find Todd Smithline on LinkedIn

Find David Wang on LinkedIn

Find Jessica Nguyen on LinkedIn
More about Docusign

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The Art of Decision Ownership

jon@caspianstudios.com (Docusign) — Wed, 16 Apr 2025 10:00:00 +0000

Our hosts and Erin Abrams, Chief Legal Officer at Via, discuss the role of in-house counsel in business decision-making. Erin emphasizes collaboration, early involvement, and building a culture of trust and safety within legal teams.

Via builds innovative software to enable our customers — cities, transit agencies, transport operators, school districts, universities, and corporations — to transform their legacy transportation systems into advanced digital networks.

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Key Quotes:

“ In addition to having a framework for how decisions are made, I think it's really important to have a framework around the life cycle of what you're trying to accomplish. And I think of it very much in sort of a product lens, but what I've seen be really successful at organizations, especially as they're starting to scale, is really going to the teams and saying things like, "legal can't come at the end.””

“With our joint ownership model, I think part of that means not running away from the consequences of your decision and saying, okay, we mitigated this risk to a place that the business and the legal team felt comfortable.”

“There's not necessarily tons of in-house positions for litigators, but what you can do is become a professional risk mitigator. You can kind of shift and say, okay, I'm really good at pattern recognition. I know what has led to litigation in nine out of 10 cases. So now that I'm looking at this much earlier in the pipeline, I'm looking at it and a contract that seems vague. You know, there's an area of sort of like a gray area. You know, it feels a little bit squishy to me. I've seen litigation result in similar circumstances. Okay, well, this is like a risk I can mitigate.”

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Time stamps:

00:48 - Meet our co-host Ken

04:01 - Meet our guest Erin

09:25 - What effective partnership looks like

14:18 - Evaluating business risks

21:41 - Making challenging decisions

28:35 - Using compliance as a competitive advantage

31:35 - How to hire well

42:53 - Keep or redline?

45:30 - Where to find Erin

45:52 - Final takeaways

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Links:

Find Ken on LinkedIn

Find Erin on LinkedIn

Find Jessica on LinkedIn
More about Docusign

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Legal’s Role in Mitigating Cybersecurity Risks

jon@caspianstudios.com (Docusign) — Wed, 12 Mar 2025 14:45:35 +0000

Aaron Kornblum, head of legal at Oleria, discusses why security functions are increasingly important for legal departments. Aaron covers the evolution of security threats (from hacking to phishing to smishing), and describes the importance of identity management. Listen for insights on integrating security practices, fostering accountability, and leveraging legal frameworks to enhance both security and customer trust.

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Key Quotes:

CINDY: The best defense is a great offense in terms of, do we have our processes in place? Do we have our playbooks? Have we tabletopped? and this is assuming you have all your fundamentals, like all your tools, technology in place to really establish the security for the company.

AARON: It's that phishing attack to get Cindy's username and password. It's that smish, it's that fake text message to Jessica that is purportedly from her CEO asking for the password to send a wire transfer to the bank account. It's more and more prevalent to get in the door and then do all kinds of bad things once they're inside that juicy interior environment. So understanding what normal behavior looks like within your own environment, within your own ecosystem, is more important than ever. That hygiene, if you will, of accounts and account credentials, passwords, two factor auth, or multi factor authentication, to ensure that the person trying to log in really is the person trying who's trying to log or no one are supposed to be logging in.

AARON: If you think about some of the areas that we just touched on, so information security, so that building the great wall to keep out folks. But also inside the company, provisioning access and then reporting or doing compliance work. These might be separate teams within a single organization. Maybe it's a small company, and it's one person. But regardless, having that robust communication between the different parts of the company responsible, say for, maybe it's the CIO, and the CTO, and the Head of Legal or GC, and then the Chief Information Security Officer, each one of these professionals has a role in helping to build this portfolio of defensive measures.

AARON: What do you have in place to protect your identity security? How often do you conduct training for your employees? It's much more difficult to secure, much more expensive to, to take down.

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Time stamps:

00:37 - Meet our co-host, Cindy

01:58 - Meet our guest, Aaron
05:34 - Security incidents that keep us up at night

07:27 - Being prepared

15:43 - Ensuring cohesion

19:21 - Risk mitigation

25:43 - What’s in the news

34:14 - Keep or redline?

38:16 - Final take aways

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Links:

Find Aaron Kornblum on LinkedIn

Find Cindy Rosser on LinkedIn

Find Jessica Nguyen on LinkedIn
More about Docusign

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Mastering Influence as Legal

jon@caspianstudios.com (Docusign) — Wed, 12 Feb 2025 14:00:00 +0000

In legal leadership, credibility is key. In this episode, we’ll discuss the importance of earning and maintaining influence. Lisa Keith, General Counsel for Steve Madden, emphasizes aligning legal counsel with your business’ goals, and how legal professionals can effectively take part in business decisions. Tune in to gain practical advice on enhancing influence within your organization, balancing business and legal perspectives, and building crucial relationships with key stakeholders.

Steven Madden, Ltd. is globally recognized as a leading company in the fashion industry. What began as a modest $1100 investment in 1990 has developed into one of the most iconic brands in footwear.

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Key Quotes:

"I would say that you really need to pick your battles… I think you have to figure out the right advice to give within the confines of the business you work for and what is realistic, you know? And so I think if you come up with something that is palatable to the business. Then they will hopefully listen to you."

"I often try to think of my job as kind of like the moral and ethical center of the company. And I think to be a general counsel, you have to have a very strong sense of values… I'm not saying you have to be like a goody two shoes, but you have to kind of have a good sense of what you think is right and wrong and you have to let that guide you and your decision making. So sometimes it's not even about the legal, it's just about your instincts of morality."

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Time stamps:

01:13 - Question of the Day

02:49 - Jim’s journey

06:47 - Lisa’s journey

10:31 - How to influence business

15:16 - GC/CEO relationships

25:54 - Acting with integrity

36:28 - Keep or redline?

41:14 - Find Lisa Keith on LinkedIn

41:54 - Final takeaways

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Links:

Find Lisa Keith on LinkedIn

Find Jessica Nguyen on LinkedIn

Find Jim Shaughnessy on LinkedIn
More about Docusign

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Trailer

jon@caspianstudios.com (Docusign) — Fri, 31 Jan 2025 20:52:40 +0000

The best in-house legal teams aren’t just legal. They help their organizations solve complex issues, make the right decisions, and even grow their businesses. That’s right, legal isn’t just a cost center.

In-House is a podcast featuring top leaders in the legal industry. Tune in as Jessica Nguyen, award-winning Deputy General Counsel of AI Innovation and Trust at Docusign and former Chief Legal Officer of Lexion, interviews leading in-house counsel and legal experts. Our guests navigate the ever-shifting landscape of the latest issues, current events, and regulations - while balancing the needs of their organizations.

Whether you’re new or highly experienced, In-House is here to help you enhance your career.

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