Paul Hollerbach knows the Rocket Lawyer business from nearly every angle. Before becoming CEO, he served as the company’s Chief Financial Officer, where his role required him to understand not only the numbers, but what was driving them — from customer behavior and product performance to where the company was investing and why.

Now, as CEO of Rocket Lawyer, Paul brings that same analytical mindset to a much broader job: deciding where Rocket Lawyer goes next and leading the company’s strategy and continued evolution as an online legal platform.

I got the chance to ask him about Rocket Lawyer’s strategy, how the legal-services landscape is changing, and how his experience as CFO has shaped the way he leads the company as CEO.

Interview with Paul Hollerbach, CEO of Rocket Lawyer

When you describe Rocket Lawyer to someone today, what do you want them to understand about the company?

Rocket Lawyer is all about helping small businesses, families, and everyday people take care of their legal matters. We’re passionate about making legal help accessible and easy to understand for the individuals, families and small business owners who may just avoid it altogether because it feels way too expensive or intimidating.

We’ve been doing this for a while now, and we really know the legal space. Right now, we’re using AI to accelerate how we make legal protection accessible to everyone — specifically by pairing AI native experiences with our network of licensed attorneys in ways that completely modernize how legal services are delivered.

What is Rocket Lawyer particularly good at right now, and where do you think the company has the biggest opportunity to get better?

We’re really good at serving small businesses — especially those with under ten employees — as well as families and individuals. That’s always been our sweet spot. It’s been an underserved market due to cost and complexity, but everyone has a right to the exact same quality of legal protection regardless of their size or budget.And the opportunity here is massive. You’ve got around 35 million SMBs in the US, with 4-5 million new ones starting up every year. Our goal is to build the modern legal service for them — combining smart AI solutions with our deep legal data, and weaving that seamlessly into our attorneys’ workflows. At the end of the day, it’s about giving people the best of both worlds: great technology and real human legal expertise.

The way people access legal help is changing quickly — from AI to online legal services to new ways of connecting with attorneys. Where do you think Rocket Lawyer fits into that change?

We’re definitely not trying to replace attorneys — they’re an absolute necessity. AI is fantastic for initial research, figuring out where you stand, and supporting you through tasks you choose to do DIY. But when you want true legal advice and services, you need a human lawyer. What we’re doing is stripping away all the friction between facing a legal issue and getting it resolved, whether you do it yourself with AI tools or connecting with a lawyer who knows laws relevant to your unique situation inside out. The companies that win here will be the ones blending great tech with real legal expertise in a smooth, trusted, and secure way.

When you think three to five years ahead, what do you want Rocket Lawyer to be known for?

I want us to be known for completely reimagining how legal services are delivered for small businesses and families by bringing technology and real human expertise together. Ultimately, I want Rocket Lawyer to be the platform people truly trust as their go-to legal partner in running their business or taking care of their family.

You’ve spent your career looking at businesses through finance, operations, and strategy. Which experiences before Rocket Lawyer most shaped the way you think about building and growing a company today?

First, you have to be in a large, growing market that’s ready for tech innovation. If you have that, you’re in a great starting spot. From there, it really comes down to disciplined execution on a clear strategy. You need great operators who act with total integrity and like to move fast. When you empower those leaders and give them room to run, great things happen.

I’ve seen a company scale from tens of millions close to $10 billion in revenue. Sure, the market and timing were right, but what made it happen was leadership executing with high velocity while building a real foundation for scale — hiring the right people, modernizing tech, and streamlining processes. Without that infrastructure upon which you can scale, companies just stumble when they start hitting real size.

You were looking at many of these same questions as CFO before becoming CEO. Did stepping into the CEO role change the way you thought about Rocket Lawyer’s opportunity?

I still see the exact same massive opportunity to modernize legal services that I always did. The difference now is that I’m responsible for driving that vision across the entire company and making it happen, rather than just building the financial architecture behind it.

I’ve always been pretty hands-on with strategy and operations, so it felt like a natural step. The most rewarding part has definitely been getting closer to the product, watching our development velocity pick up, and empowering our leaders to do their best work.

Are there parts of that CFO mindset that you’ve had to adjust or even resist as CEO?

As a CFO, you’re always thinking about return on investment and trade-offs. The shift for me as CEO has been realizing that 'return' isn't always a quick financial metric. Sometimes the true return is building customer trust, growing brand equity, or developing new AI capabilities for the long haul. There’s definitely a bit more art involved in the CEO role, and honestly, I find that really refreshing.

You’re known for asking a lot of questions before making a decision. When someone brings you an idea, what are you usually trying to understand first?

I'm usually trying to figure out if the team has really thought through how this idea helps the customer. How does it improve their experience, and in turn, how does it drive business results? Those two things go hand in hand, but you always have to start with customer value. Too often, people chase shiny objects or try to react to a competitor without thinking it through. There’s nothing better than doing the research, crafting a solid plan, getting everyone aligned, and executing it. But it all starts with a thoughtful vision.

When do you decide you have enough information and it’s time to make the call?

It’s when I’ve pressure-tested the main assumptions and clearly understand the impact on the customer and business KPIs. If the data points us in a clear direction and the team has a solid plan to iterate and learn as we go, waiting for 100% certainty just slows you down. We like to think deeply, but we’re doers at heart—and often, the fastest way to get real feedback is just to ship the product.

What do you hope employees understand about the way you make decisions?

I want them to know that my questions aren't a sign of doubt — they're just my way of making sure we're totally aligned on the ‘why.’ If I’m digging into the details, it’s because I want to ensure the customer value and business impact are crystal clear. I value rigorous thinking, but I value momentum even more. At the end of the day, my decisions come down to a simple question: Does this make things better for our customers, and does it drive real results for the business?

About Paul Hollerbach

Paul brings more than 25 years of experience across finance, operations, strategy, and business leadership. A graduate of Cal Poly San Luis Obispo and a Certified Public Accountant, he began his career at Ernst & Young and KPMG before moving into financial planning at Silicon Graphics. He later spent nearly a decade at Yahoo!, where he held senior finance roles including Vice President Corporate Controller and Vice President of Financial Planning and Investor Relations, before serving as Chief Financial Officer of Current TV.

His history with Rocket Lawyer goes back more than a decade. Paul first joined the company as CFO in 2012, serving in the role for seven years before transitioning to an Advisory Board Member. He returned as CFO in 2021 and stepped into the role of interim CEO in 2025 before becoming Rocket Lawyer’s Chief Executive Officer.

That combination of deep familiarity with Rocket Lawyer and a career built around finance, strategy, and operational decision-making gives Paul a distinctive perspective on both where the company has been and where it is headed.