GC Sidebar: Doe Gregersen, General Counsel at Nav Technologies

In this GC Sidebar Season 2 episode, Paragon Legal CEO Trista Engel speaks with Doe Gregersen, General Counsel at Nav Technologies, about what it really means for legal teams to operate as strategic business partners.

Doe shares why relationships are at the center of effective in-house leadership and how trust allows legal teams to be brought into conversations earlier, influence decisions more meaningfully, and help businesses move forward rather than simply react to risk. She discusses why the role of legal isn’t to eliminate risk entirely, but to help organizations understand, contextualize, and navigate it thoughtfully.

She also reflects on how legal leaders can shift from being viewed as blockers to enablers, why embedding legal into business decision-making matters, and how strong relationships ultimately drive both influence and impact across the organization.

Full episode now available.

Read the Full Conversation

Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Doe Gregersen, General Counsel at Nav Technologies.

Trista Engel:

Welcome to GC Sidebar, a short and sharp conversation series with leading general counsel about the decisions, reflections, and people behind the title.

I’m Trista Engel, CEO of Paragon Legal, and today I’m joined by Doe Gregersen, General Counsel at Nav Technologies, a credit and financial health platform focused on helping small businesses build credit.

Throughout her career, Doe has worked at the intersection of credit access, lending, and financial inclusion, particularly for individuals and small businesses, while also dedicating her time to community organizations.

Doe, I’m so glad you’re here. Thank you for joining me.

Doe Gregersen:

I’m so excited to be part of this series. Thank you so much, Trista.

Trista Engel:

Awesome. Let’s jump in.

Trista Engel:

What’s one issue facing legal teams right now that you think is overrated or premature?

Doe Gregersen:

I hope I’m not saying the same thing everyone else has said, but for me, it’s the AI bubble.

We’re hearing about it from every direction. One message is that AI is going to replace your job. Another is that legal has to protect the company from AI because it’s going to take all your data and information. Then there’s the concern that employees are using AI on their own and nobody knows what’s happening.

There are so many conversations happening around it.

At the same time, I’ll attend presentations and be surprised by how many attorneys raise their hands when asked if they’ve never used AI before.

To me, AI is a great tool. It’s a value-add, and it absolutely should be part of our day-to-day work. But in many ways, it’s just another vendor or another piece of software. The hype around it feels outsized for where we are today.

Trista Engel:

I love that you call out how many people haven’t really used it because there is a disconnect between the hype cycle and what’s happening in reality.

At the very least, there’s a wide spectrum of usage. The hype cycle gives everyone FOMO and makes people feel like they’re behind the curve. The reality is that most people aren’t behind. Most people are learning and hopefully testing because it’s happening and it’s coming. We should be learning how to harness it, but in a smart way.

Doe Gregersen:

That’s such a great point.

There’s also this pressure that you have to use AI or you’ll be left behind. But adopting it just for the sake of adopting it doesn’t make sense.

You need an actual use case. You need to know what outcome you’re trying to achieve and focus on that instead of treating AI as either a magic solution or dismissing it because it generated a picture with five fingers.

Trista Engel:

Exactly.

I’m also wary of studies that claim things like “90% of lawyers are using AI.” There’s a huge spectrum of usage. Having a ChatGPT account and asking a few questions instead of using Google counts the same as thoughtful, sophisticated integration into workflows. Those aren’t equivalent use cases.

Doe Gregersen:

Absolutely. I’m glad we’re aligned on this one.

Trista Engel:

What’s the most valuable lesson you’ve learned as a GC?

Doe Gregersen:

Through the years, the most valuable lesson has been realizing that my job isn’t to protect the business from itself.

My job is to enable the business, be a thought partner, work across teams, identify risks, and help my business partners evaluate them. I’m not the last line of defense whose role is to say no to everything.

Trista Engel:

That’s such a great point for people listening.

You have to transition from thinking of yourself as an advisor to the business to thinking of yourself as part of the business. Especially if you come from a law firm environment, that’s a critical mindset shift.

Doe Gregersen:

Absolutely.

I worked at a law firm during law school as a paralegal, but after graduation I went directly in-house. Because of that, I grew up professionally as part of the business while also being a lawyer.

I’ve seen a stark difference when working with outside counsel. Sometimes they’ll explain what the law requires, and I’m thinking, “I understand that, but the system can’t do that. I need another way.”

Understanding that we aren’t going to eliminate all risk, that we will carry some risk, and that our role is to help the business achieve its goals while managing that risk has been huge.

Trista Engel:

Very cool.

Trista Engel:

What’s the best career advice you’ve received or given?

Doe Gregersen:

This is such an interesting question.

It didn’t really come as advice, but I treat it that way. During a job interview, I asked a general counsel what the biggest part of her job was.

She told me, “Relationships are the job.”

That really stuck with me and changed the way I thought about my role.

I’d always built relationships. I understood trust was important and that getting to know people mattered. But it wasn’t intentional. It was more of a byproduct of working together.

After that conversation, I made relationship-building a deliberate goal.

Whenever I’m at work, I’m building relationships, connecting with people, and reaching out. I want to be more than the lawyer people come to with questions. I want to be a true partner who’s part of their everyday workflow.

Trista Engel:

I love that answer.

Everything we do is built on trust, and relationships are how you build trust. It’s a very different way of thinking about your job than simply focusing on the substantive legal work.

You still need that expertise, but then you have to think about how you communicate it, how you influence outcomes, and how your advice gets incorporated. It’s all about relationships.

Doe Gregersen:

Exactly.

Trista Engel:

How have you leveraged flexible legal talent to augment your in-house team?

Doe Gregersen:

I’ve leveraged it in a couple of different ways, and in both situations I worked with Paragon Legal.

What we’ve been able to do is outsource specific projects that were too large for the team at the time and would have significantly increased our legal spend if we’d used outside counsel.

For example, at a previous company, when I joined, we didn’t have a proactive vendor management or contract management program. We had contracts, but we needed someone to review them all, identify expiration dates, notice requirements, and other key information.

We worked with Paragon Legal on that project.

Another example involved extensive licensing requirement research across all 50 states. That’s not something you want to send to a law firm, but it’s also difficult for a smaller legal team to absorb internally.

Both projects were very positive experiences.

Trista Engel:

I’m so glad to hear that.

I love those examples because they’re projects that really enable the business and need to get done, but they aren’t necessarily part of the team’s day-to-day work.

Too often those projects get pushed to the back burner. Sometimes they can’t, especially when they’re regulatory. Finding a way to get that work done can make a real difference for the business.

Doe Gregersen:

Exactly.

I’ve had a very positive experience with Paragon, and I’m always looking for opportunities to shorten timelines by bringing in someone who doesn’t need to be a permanent hire but can still have a significant impact.

Trista Engel:

Absolutely.

Trista Engel:

If you weren’t an attorney, what would you be?

Doe Gregersen:

That’s a tough question because I have so many hobbies.

I’m always doing DIY projects, crafting, and trying things I’ve never done before. I’ll see something and think, “I wonder if I can make that.”

But I don’t know if I’d enjoy it as much if it were my job.

Ever since high school, I wanted to be an attorney. I don’t really know why. It was just my focus, so I never seriously considered other career paths.

Looking back, project management sounds fascinating because it’s fast-paced and different every day. Maybe a project manager. Maybe a carpenter.

I honestly don’t know. There are so many possibilities.

Trista Engel:

It sounds like you found exactly the career you were meant to be in.

I love that you skipped the traditional law firm path and went straight to where you wanted to be.

Doe Gregersen:

I definitely think in-house was the perfect fit for me, and I’m very happy I got there quickly.

Trista Engel:

Paragon turns 20 this year. What’s one memory from 20 years ago that still stands out to you?

Doe Gregersen:

First, congratulations. That’s a huge milestone.

Trista Engel:

Thank you very much.

Doe Gregersen:

I hope there’s a big cake or champagne involved.

Trista Engel:

Absolutely.

Doe Gregersen:

Twenty years ago, I was in law school while working full-time. I lived about an hour away from both work and school, so I was sleeping maybe five hours a night.

Honestly, it’s not a time I necessarily want to relive.

It was a constant grind of just trying to get through.

Trista Engel:

That’s very real.

If the version of you from 20 years ago could see you now, she’d hopefully think it was all worth it.

Doe Gregersen:

For sure.

It was absolutely worth it. Even the journey itself was necessary and valuable in getting me where I am today.

But when I think about 20 years ago, that’s definitely what comes to mind.

Trista Engel:

We’ll ask you again in a few years. Maybe a different memory will rise to the top.

Doe Gregersen:

Perfect. Let’s do that.

Trista Engel:

Awesome. Thank you so much, Doe. This was a lot of fun. I really appreciate you being here and sharing your journey.

Doe Gregersen:

Thank you, Trista.

Trista Engel:

That’s a wrap on today’s episode of GC Sidebar. Catch more great conversations on our website at paragonlegal.com.

Thanks for tuning in.