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A Q&A with Everlaw's VP of People Leah Fine

by Colleen Haikes

We are thrilled to welcome our new Vice President of People, Leah Fine, to the team. Leah joins Everlaw having established her career as a management consultant at Bain, before pivoting into the People function where she helped scale brightwheel from 50 to 500 team members. 

Leah recently sat down with us to share how she became passionate about leading people, how the mission-driven nature of Everlaw drew her to this role, and how the People function will continue to evolve in the coming years.

We’ll start with some basics. Tell us a little about yourself.

I was born and raised in Sacramento but spent a ton of time in New York and lived abroad for a number of years in Latin America and China before moving back home to San Francisco, where I live with my partner, our toddler, and our neurotic dog.

I’ve had a circuitous route and ultimately fell in love with both company building and the People function. I believe that it’s our people who really define a company’s trajectory and I love learning about individuals to understand what they care about and what motivates them, and I am fascinated by how a group of people can best work together to achieve big things. 

Everlaw VP of People Leah Fine
Everlaw VP of People, Leah Fine

What drew you to joining the Everlaw team?

First, Everlaw’s mission. At my core, I am a mission-driven person, and I like to work with mission-driven folks. Second, I wanted to be a strategic partner to the business. It was clear to me that AJ and the leadership team view people, both the function and Everlawyers, as critical to the success of the company. Finally, I loved the people I met in the interview process. Building a company is hard, and I want to do it with exceptional, kind, and values-aligned colleagues. 

You mentioned that you had a circuitous route to becoming a People leader. How has your diversity of experience shaped your approach to leading people and building team cultures, and shaped you as a leader? 

I have a non-traditional route into the People function - and that has shaped my approach to both leadership and my function. I'm curious about different ways to do things, and I try to avoid being too rigid about one “right way” to do things. I think that comes from spending the first five years of my career working in Brazil and China across wildly different industries including a law firm, publishing, government, and non-profit. Navigating different cultures, ways of working, and languages gave me flexibility, creativity, and, frankly, adaptability in how I approach challenges.

Having a broader business background has influenced my approach to my role. I am grateful for my time working as a consultant at Bain. It gave me a strong toolkit for understanding how businesses operate, and for solving complex and novel problems. A great people strategy should always work backwards from what we are trying to achieve as a business, while operating in alignment with our values. 

And, of course, my work is influenced deeply by my prior experiences within the People function, most significantly at the startup brightwheel, where I helped us scale from 50 to 500 team members. 

What role does continuous learning play in maintaining relevance in one's career?

There’s so much change in careers now, both driven by individuals looking to tackle new challenges and by external changes. Just look at the past few years - navigating a global pandemic, experimenting with a radical shift to work from home and return to office, changes in the funding environment for startups, and the rise of different technologies. The ability to adapt and learn and move forward has been critical to success. 

I actually think about this more with my daughter than at work. I think having a growth mindset comes down to self-confidence— not arrogance that you know everything or are best—but the self-belief that you can learn and get better with time and effort. More than that, it’s the self-confidence to tolerate failure. I want to instill in my daughter the confidence to not know, to struggle, and to take risks. 

How do you see the role of Head of People evolving in the coming years? 

There has already been an important shift over the past decade to recognize the People function as a core part of the business, and a place for innovation and strategy. I expect that to continue.

The role will increasingly demand People leaders with strong business acumen, and the ability to develop novel solutions to complex people problems. I’ve seen a ton of innovative thinking from peers in recent years, and I’m inspired by those challenging HR orthodoxy and driving innovation that best support the people and the businesses we serve.

What’s on the docket for your first 90 days at Everlaw?

You’ve asked a lot of questions about learning, and that’s my focus for my first 90 days. I want to learn as much as I can about people, the business, and our customers. That’s the foundation that I need to build an informed strategy and roadmap for the people function. So, please come talk to me!

Last question: What do you like to do in your free time?

I spend the vast majority of my free time with my family. Outside of that, I love going on walks with my dog, trying new restaurants or my husband’s new recipes (he’s the cook!), and supporting the San Francisco Opera, as well as catching up on reality TV.