Deborah Holstein believes that understanding the customer isn't optional, and that data fluency is a core discipline, not a nice-to-have — because deeply understanding the customer is the thing that should drive every strategic decision a company makes. Her approach is to stay relentlessly focused on what needs to happen, and to align the people and resources of the business to actually make it happen.

Deborah joined Rocket Lawyer in 2023 as Chief Growth Officer. She leads Rocket Lawyer's customer-first growth and go-to-market strategy, bringing together customer insights, data, brand, positioning, acquisition, and retention to inform both marketing and product strategy. She also leads Rocket Lawyer's Partnerships and International teams.

I got the chance to ask Deborah why she joined Rocket Lawyer, how she thinks about the brand's evolution, how AI and attorneys fit together, and what she's learned along the way that she wants to pass on to emerging leaders.

Interview with Deborah Holstein, CGO of Rocket Lawyer

When you joined Rocket Lawyer, what did you see in the company and the opportunity that made you want to be part of it?

When I looked at Rocket Lawyer, what I saw was a real opportunity to fix something that had been broken for a long time: how individuals and small business owners get access to the legal protection they deserve.

Given the complexities of the legal system and the cost of legal services, too many people have been forced to choose between muddling through a legal matter on their own or investing their time and money in finding and paying an attorney — neither of which meets their needs.

Rocket Lawyer membership changes that. Now everyone has an affordable way to get and stay legally protected, with a combination of trusted legal AI and seamless access to the right attorney, all in one membership.

Rocket Lawyer was historically known as a place to create legal documents. Today the experience brings together AI, attorneys, filings, and more. How do you think about what the brand stands for as the company evolves?

Rocket Lawyer is no longer just a way to create your own legal documents. Now we are a place for every individual and small business owner to come when they face any legal matter.

Documents are the foundation of the legal system, so that's where Rocket Lawyer started. Over the years, we built on that foundation, adding more ways to help individuals, families, and small business owners handle the full range of legal matters they face — contracts, disputes, hiring and firing employees, starting a business or staying compliant with business filings, trademarks, succession and estate planning, and more.

Our brand has stood for providing affordable access to the protections of the law through a combination of technology and professional legal services from attorneys. Now, with the rapid growth and user adoption of AI, we've been able to accelerate bringing that vision to life for more and more people.

What I hear directly from our members is how much they value being seamlessly connected with an attorney about any legal matter when they choose to, as part of their membership. They consistently share that they feel so much more confident about their decisions and action plan after talking through the specifics of their unique situation.

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

When I think a few years ahead, I want Rocket Lawyer to be known for helping ensure every individual and every small business owner has a strong legal foundation from day one. That means an affordable legal membership — combining trusted legal AI with real human attorney guidance — so that everyone can start out, and stay, legally protected.

I want access to legal protection to be so ubiquitous that it's included on registries as a graduation, housewarming, or shower gift, because everyone deserves to live their lives with the confidence of having a strong legal foundation. And I want every small business owner to approach their contract negotiations on the same level playing field as companies with large internal legal teams.

I want Rocket Lawyer to be known for making sure legal protection isn't something only big companies or wealthy individuals can access. It's something everyone starts with.

Your career has taken you through companies at very different stages — from startups to companies like Yahoo, Cisco, and Dropbox. What have those experiences taught you about what a Chief Growth Officer needs to understand beyond traditional marketing?

My experience at companies at very different growth stages has given me the ability to see around corners and to recognize what's needed for a company's next stage of growth. That allows me to diagnose what the business needs to do right now in order to be where we want to be six, nine, or twelve months from now.

One of the clearest examples of why that matters is that a go-to-market strategy isn't just something that happens after product decisions are made. In freemium, product-led-growth businesses, it is the desired go-to-market that informs necessary aspects of the product experience. Users need to experience a short time to value, there need to be viral loops, and the product needs to deliver persistent value — or cost-efficient growth simply cannot happen.

Sales-driven motions work differently, because the buyer and the user generally aren't the same person, and enterprise-size contracts can support the costs of onboarding and training. Therefore, the product experience requirements will be different.

Your business's go-to-market strategy is your business's growth strategy — it is not one size fits all.

How should what a company learns about its customers, positioning, market shifts, and performance influence where the business invests or what it builds next?

Every business must have a deep understanding of its customers. Understanding their needs, pain points, and behaviors informs business, product, and marketing strategy.

A small business owner faces multiple legal situations in running their business, including negotiating and signing new contracts or enforcing existing ones, hiring and firing employees or independent contractors, staying compliant with business filings, protecting brands with trademarks, and planning for the future with succession and estate planning.

Addressing just one of these legal situations is good, but proactively recognizing how each one fits within the many legal matters business owners face ensures Rocket Lawyer creates holistic, valuable experiences for its customers.

Does AI-driven discovery change more than the marketing channel itself? Does it change how companies need to position and explain what they do?

For years, marketing leaders have struggled to justify necessary investment in brand and awareness, because bottom-of-funnel, non-brand paid search has just been easier to measure and defend in a budget meeting. Reliance on non-brand paid search has always been a risky game, because not all of your potential customers are searching for a solution right now. Your target audience must know who you are and what you do, so that when they do have that need, they navigate straight to your site or app to engage and buy.

Users adopting AI for discovery makes over-reliance on bottom-of-funnel search an existential risk that cannot be glossed over. When a user asks an AI assistant a question, it is answered right there in the experience — there is no click to attribute, no last touch to credit, and the once "easy measurement" just no longer applies.

As a growth leader, I see this shift of users to AI discovery as a necessary catalyst for businesses to take a new approach to their marketing strategy and become more sophisticated in what and how they measure impact. The smartest companies made that shift well before AI answers crossed the chasm — now the laggards are playing catch-up.

As customer journeys become more fragmented, do the traditional boundaries between brand, search, content, paid marketing, PR, lifecycle marketing, and customer experience still make sense?

All marketing touchpoints need to be integrated. There is only one customer, so no matter the touchpoint, a customer should see a consistent message. Each touch builds on and reinforces the others, and they can't feel disconnected.

The delivery and optimization of each channel and touchpoint still requires specialized expertise, so teams still require specialization. I think of it like an orchestra, where there is an expert playing each instrument and each section relies on the same conductor to bring their parts together into a coherent whole for the concert. The integrated go-to-market strategy is the conductor, ensuring all the talented musicians together deliver the music that engages and moves each customer.

At Rocket Lawyer, that shared piece of music is simple: no matter which touchpoint, the customer should walk away understanding that Rocket Lawyer is the place to affordably address any legal matter they face.

When the channels themselves are changing this quickly, how do you make sure the company is adapting its strategy rather than just optimizing yesterday's playbook — or chasing the latest shiny object?

This is a challenge for every leader in every function, not just growth teams. Many teams default to incremental approaches because that feels safest. But when technology and user behavior are changing rapidly, adaptation is rarely incremental. It requires thinking differently about the problem and working in different ways — all of which will feel uncomfortable.

To help teams feel confident about thinking differently, I work to keep them grounded in the fundamentals of understanding the customer. If we know customers' needs and pain points, and we know they now have some new behaviors and expectations, then the work is still creating strategies to reach and engage them with creative, compelling messaging and offers wherever they are.

What advice do you find yourself giving emerging leaders over and over again?

What I find myself reminding emerging leaders about most is to stay curious. Stay curious about your market, your customers, your business, and your functional area, because the only constant in any career is change.

And because getting anything accomplished in any size business requires effectively communicating and collaborating with many different people, the best leaders also stay curious about the people they work with. To be effective, you need to get curious about them as individuals — what they care about, how they like to make decisions, whether they prefer written communication or meetings, and so on.

Whenever there are cross-functional communication challenges, leaders must always communicate and operate from a place of putting the business outcome first, because it's rare that someone is actually trying to sabotage your project or your day. It's best to lean in and get curious about what they think and what is important to them. Many times it's something as simple as not having a shared vocabulary, which becomes enough of a gap to create a misunderstanding.

About Deborah Holstein

Deborah Holstein is Chief Growth Officer at Rocket Lawyer. She holds an MBA from NYU Stern, where she double-majored in marketing and statistics, and a Bachelor of Business Administration from Georgetown University.

With more than 15 years in technology and SaaS growth and marketing leadership, she has led high-performing teams at companies of all sizes and growth stages. Before joining Rocket Lawyer in 2023, Deborah held marketing and growth leadership roles at companies including Yahoo, Cisco, Hightail, and Dropbox.

Deborah advises and invests while also mentoring emerging leaders. She has written extensively about business strategy, growth, marketing, and leadership.