In this premiere episode of GC Sidebar, Paragon Legal CEO Trista Engel sits down with Jennifer Miller, General Counsel and Corporate Secretary at Grammarly, for a candid, four-question conversation on leadership, legal innovation, and career wisdom.
From navigating balloon-powered internet to driverless delivery bots and now generative AI, Jennifer shares sharp insights from her diverse GC journey—including why AI is reshaping legal departments, how to lead with strategic impact, and the simple test she uses to decide when it’s time to make a career move.
Plus, find out what she’d be doing if she weren’t a lawyer (spoiler: it involves a lot of dogs). Watch now for sharp takes and real talk with one of today’s most dynamic GCs.
Prefer reading over watching? Below is the complete transcript from our GC Sidebar interview with Jennifer Miller, General Counsel at Grammarly.
Trista Engel:
Hi! I’m Trista Engel, CEO of Paragon Legal, and welcome to GC Sidebar, a short and sharp conversation series with today’s most forward-thinking general counsel.
In just four questions, we cover the legal industry, leadership, careers, and a little fun.
Today I’m joined by Jennifer Miller, General Counsel and Corporate Secretary at Grammarly, the AI-powered writing and productivity assistant trusted by probably many of you watching, along with over 40 million others worldwide.
Jennifer began her legal career at Morgan Lewis before moving in-house to companies including Cisco, HP, and Gigamon.
She stepped into her first general counsel role in 2018 at Loon, an Alphabet Moonshot company, and then Starship Technologies, before joining Grammarly as GC in 2023.
She’s gone from tech hardware to driverless bots to balloon-powered internet to generative AI, and I know she’s got some great stories to tell. Jennifer, thanks so much for being here.
Jennifer Miller:
Oh, thank you so much for inviting me to join you.
Trista Engel:
Let’s jump in. What is the one biggest change in the last 5 to 10 years that has impacted the legal department the most?
Jennifer Miller:
Oh, I think, given where I am right now, the one biggest change in the last 5 to 10 years that’s impossible to ignore would have to be AI and the maturation of machine learning generally.
It’s part of the reason why I decided to go to Grammarly as General Counsel. We really feel that AI is a productivity augmentation that helps people be so much more effective and efficient.
I think it has taken the legal department by storm in so many ways, both good and bad. Recognizing that many of the tools available are still… some of them that aim to replace human effort have so many problems. They have errors, they hallucinate, things like that.
So it’s hard for legal departments. Grammarly and other tools like Grammarly and Coda help people become more productive. I think those augmentation tools are what legal departments can bring on to really be much more helpful to the team.
But it’s hard because some of these tools are not people-replacement ready, and that leads to a really uncomfortable tension where you have to do more with less, but less, if it leads to errors, can bring too much risk for a business.
Trista Engel:
Yeah, that’s such a great point, and so interesting for you to be inside a company that’s really doing that augmentation for others and leading the way, being on the forefront in legal as well as in AI.
Jennifer Miller:
Yeah, that’s right.
Trista Engel:
What’s the most valuable lesson you’ve learned as a GC?
Jennifer Miller:
Such a great question! The most valuable lesson that I’ve learned, I’ve been General Counsel now at a couple of different companies, and I think it’s clear to me that the most valuable lesson is that to be effective, the General Counsel must lead.
Assuming that he or she has a team, he or she, and the team as a whole, must be really strategic thinkers about the business.
I always say that I view myself as a business executive with a legal lens. And if you’re not putting the business first, and the General Counsel and the legal team isn’t looking ahead at how a company grows its revenue, avoids problems, mitigates risk, the business team will just stop including legal.
Then the legal team is left out of the important decisions. I think the most strategic legal counsel teams are by far the most effective because they’re really helping to drive the business forward. To be the most valuable, it has to be the most strategic.
Trista Engel:
I fully agree with that, and love the lens of putting the business hat on first with the legal lens. That’s great.
Jennifer Miller:
That’s right. And I recognize not every General Counsel role is a strategic GC role. Some are more transactional, and that’s totally okay. However, I think as general counsels take a more prominent role in their company, they must be really strategic.
Trista Engel:
Absolutely.
What’s the best career advice you’ve received or given?
Jennifer Miller:
So much career advice I’ve received over the years, and then some I’ve turned around and given.
I think I have two things I’d love to talk about.
First, I was on a panel once, and someone asked us this question, they asked, “How do you know when it’s time to leave your role?”
This is something someone shared with me a long time ago, and I’ve now taken it in and shared it a number of times. I firmly believe that you have to know when’s the right time to leave, to join a new company, all those things.
But I think the key test is that a person should always be either learning or earning. Assuming one of those is true, it’s a good place to be.
If you’re learning or earning, some money, whatever it might be, that is the test. If it ceases to be true, that’s when it’s time to seriously think about moving on to the next challenge.
What’s interesting, I was at a dinner earlier this week, and the woman sitting next to me, I hadn’t met her before, but she had heard that panel where I talked about, “How do you know when it’s time to leave?”
She said that hearing “learning or earning” in her head caused her to leave her role and get a new job. She was really happy and thanked me. I thought, “Wow, okay, I guess that was impactful.”
Trista Engel:
Yeah, you rarely get that kind of feedback on your advice.
Jennifer Miller:
I know. That question to me was so timely because she literally just told me that this week.
And then the second piece of guidance that I give people is something that has come from my own journey, as I’ve gone from law firms to in-house, to becoming more senior and now General Counsel, everything is a season in life.
It’s perfectly appropriate to make decisions based on that season. People often feel like the decision they’re facing in the moment is something that has to be true forever. I really don’t believe that’s true.
An example, when my two sons (now in college) were in private preschool, I made different financial choices. I wanted to be at a company that had liquid stock because I needed the money to pay for preschool.
Then they went to public elementary school, and suddenly I had a different season. I could take more risk in my legal career.
As they got older, I could take bigger jobs that required travel. I was talking to a woman I mentor, and she said she didn’t know how to decide, she wanted to stay home briefly with her young child.
She felt that decision would derail her whole career. We talked about it being just a season of life. You come back later and pivot. Yes, you’ll have to explain.
But as long as the narrative explains why you made your choice, you can always pivot later.
You have to give yourself grace and recognize the decisions you make now might not be the same decisions you’ll make later, and that’s okay.
Trista Engel:
I love that. That’s great advice, giving yourself grace to make the decisions that feel right to you in the moment, and not fear that it’s derailing everything ahead of you. Because in fact, it’s probably getting you to the right place.
Jennifer Miller:
Indeed.
Trista Engel:
That’s great. If you weren’t an attorney, what would you be?
Jennifer Miller:
Oh, if I were not an attorney, I would own a farm and have a sanctuary for animals of all kinds, in particular dogs and cats.
We have a standard poodle at home. I would love to adopt all the dogs, all the time, and take care of them. So yes, I would run an animal sanctuary.
Trista Engel:
Well, maybe that’s in your future, Jennifer.
Jennifer Miller:
We’ll see.
Trista Engel:
All right, bonus question. Who is your favorite fictional lawyer?
Jennifer Miller:
Oh, it’s silly, but I grew up watching L.A. Law, so I’m not sure I have one especially, but that’s what made me realize I wanted to be a lawyer.
Trista Engel:
Oh, that’s fantastic!
Well, that was really fun, Jennifer. Thank you so much for sharing your insights and sharing your journey.
Jennifer Miller:
Thank you. Thank you so much.
Trista Engel:
All right, 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.
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