Introduction
Jacob Zipfel is Head of Legal & Corporate Secretary at CareRev, a Series C healthcare technology startup transforming how healthcare facilities staff their teams. With 15+ years of experience building, scaling, and protecting high-growth companies, Jacob has served as Head of Legal or lead attorney for 10+ B2B/B2C platforms generating billions in annual revenue, including Amazon’s self-service advertising business (which he helped scale 20x, reaching billions in annual revenue), Amazon Restaurants (expanded from a pilot to a 24-city platform), and REEF Technology’s ghost kitchen network (scaled 10x to hundreds of global locations).
Jacob’s career began as a commercial litigator at two Am Law 100 firms before transitioning in-house to Amazon, where he discovered his passion for building and scaling in fast-moving environments. Known for forward-thinking solutions to mission-critical business matters and high-stakes disputes, Jacob brings deep experience in product counseling, commercial transactions, risk management, litigation, marketplaces, AI, privacy, and compliance.
His philosophy is simple but powerful: legal leaders aren’t just executing; they’re redesigning the pieces of the puzzle to help the entire company accomplish its strategic objectives.
Career Arc & Foundational Lessons
Zac: Tell me about your career journey and how you ended up at CareRev.
Jacob: I began as a Big Law litigator in Chicago (Jenner & Block and Barnes & Thornburg) and enjoyed the people and the work. But I wanted to be closer to the business, not just the briefs. Over Christmas one year, my wife and I agreed I’d explore in-house. A few days later, an Amazon recruiter called. We said yes.
In Seattle, I stepped into an operating role as lead lawyer, effectively a mini-GC, for Amazon’s self-service advertising and Amazon Restaurants. This is where I discovered what I love most: building and scaling. We grew the ads business 20x to billions in annual revenue and expanded Amazon Restaurants from a pilot to a 24-city food delivery platform with thousands of participating restaurants. That training and experience rewired how I practice: solve for the business objective, move fast, build for scale, and calibrate risk with frameworks like one-way versus two-way doors. That mindset has guided my every role since.
Back in the Midwest, I joined REEF Technology (a late-stage tech startup) as AGC during its hypergrowth. REEF was building the largest network of ghost kitchens while operating a massive parking management footprint. My remit was to recruit and develop a legal team and build the supporting operating system (playbooks, standardization, simplification, and automated workflows) so deals moved faster, judgment stayed steady, and teams had a clear, confident path to “yes.” REEF was a rocket ship and a fun ride.
CareRev (a Series C tech startup) was a natural next step: a mission-driven healthcare marketplace platform with regulatory complexity. As Head of Legal & Corporate Secretary, I’ve led our legal and government affairs team and applied my Build-Scale-Protect framework. A good example is the development of our novel staffing marketplace, which greatly expanded our serviceable addressable market (SAM).
The throughline is this: I’m a business partner first. I listen, make trade-offs explicit, and help executives and boards quickly determine the best path to accomplish their objectives. That’s how I ended up at CareRev and how I lead legal today.
Zac: You’ve gone from Big Law to increasing legal leadership roles at Amazon, REEF, and now CareRev. What key shifts in mindset made those transitions successful?
Jacob: One key mindset is acknowledging that with startups and other high-growth companies, you cannot know the future. You often don’t know what will happen in six months, let alone years. While that uncertainty can be uncomfortable, accepting it is liberating. You move fast on reversible decisions (two-way doors) and are rigorous and intentional about irreversible decisions (one-way doors). You learn to design for optionality and flexibility and convert one-way door decisions into two-way doors wherever practical.
Zac: Tell me more about one-way versus two-way doors.
Jacob:Startups and other high-growth companies need to be nimble. They need to react and seize opportunities as they come and go (e.g., finding product-market fit). Decisions that function as one-way doors can be dangerous: once you’ve gone through that door, it’s very difficult, expensive, or impossible to go back (like signing a three-year exclusivity agreement that you can’t terminate). Failing to know the future is not the problem. The problem is denying that the future is contingent and uncertain, and then making important one-way decisions predicated on an anticipated future.
It’s liberating to realize: I’m not expected to know the future. What I am expected to do is build with optionality and flexibility so we can adapt as opportunities come and go. That’s an important mindset, whether you wear a legal hat or a business hat.
Zac: What is another key shift in mindset?
Jacob: Think of the company’s “big picture” or strategic objectives as the picture on a puzzle box that you and your colleagues are trying to create. The puzzle pieces might be product, sales, supply chain, finance, and legal, among others.
As a junior in-house attorney, you’re often deep in execution and focused on the pieces in front of you (e.g., negotiating a procurement contract). You may not be included in strategy sessions, let alone meetings with the CEO or board. Some companies have all-hands meetings or quarterly business reviews (QBRs); that’s helpful. But as a junior attorney, it’s still hard to see the full picture. You still need to seek that visibility.
As you move into more senior roles, you gain visibility over more pieces and the ability to reshape or design new ones (e.g., create a new contract template or workflow). If a product piece and legal piece don’t fit and it’s creating a gap, you can work with your Chief Product Officer to change the product, adjust terms, or modify a process so the fit is clean and delivers faster execution and fewer downstream issues. Remember to take a step back to ask: What’s the best way to accomplish our objective (the picture), not just with the pieces we have, but by deciding what those pieces should look like? That’s where value is truly created.
Ultimately, that’s the job of every leader: keep the objective clear, see the whole table, and design and combine the pieces so the picture comes together. That mindset makes the work more fun and rewarding. And it shows up as faster progress, cleaner execution, and fewer surprises.
Zac: How did your time at Amazon influence how you think about legal’s role in enabling growth?
Jacob: First, I learned at Amazon that my role is simple: help the business determine how best to accomplish its objectives. I frame advice to business partners as “here’s how we can achieve the objective,” tied to business impact. If my guidance isn’t landing, I’ve likely forgotten that role.
Second, speed matters. As General George S. Patton memorably said: “A good plan violently executed now is better than a perfect plan executed next week.” Move quickly on reversible decisions and slow down only for one-way doors.
Third, separate signals from noise. As a lawyer, you’re trained to spot issues. But most of that is noise. Understand what truly matters: typically, that’s only a few issues. Stay laser-focused on them.
Interim (aka Flex) Legal Staffing
Zac: You’ve had experience with the temp-to-perm and flexible staffing models at REEF. How do you see that fitting into the startup mindset of two-way doors?
Jacob: At my prior stop, REEF Technology, we hired multiple folks on temp-to-perm. It helps you onboard more quickly and retain optionality for both sides if the fit isn’t there. It can also help organizations that prefer variable versus fixed cost structures.
Zac: What do you think the next generation of flexible legal staffing will look like, especially with AI in the mix?
Jacob: Candidates need AI proficiency, including how to prompt effectively and verify outputs. The AI tools used will vary by organization, but much of the needed skill set will remain constant for the near- to mid-term future.
Automation & AI in Legal Workflows
Zac: What advice do you have for lawyers who want to start using AI in their work?
Jacob: Start in your personal life. Download the ChatGPT app and purchase the “Plus” subscription at $20 a month. Always use “Thinking” or a similar reasoning mode. Turn off training on your chats. And just start using it. This helps you learn AI capabilities and constraints and quickly upskill your use of AI for work. And it’s a lot of fun.
For example, I used AI to quickly summarize and chart results from blood work testing over 10 years, tracking items like my cholesterol, weight, and other health markers.
I also used ChatGPT to build, in one hour, a month-long lesson plan for my kids’ summer break regarding the American founding and Revolutionary War. The daily lesson plans included a script, citations to source materials (e.g., Library of Congress online materials), recommended kids’ books on the topics I could purchase straight from Amazon, local historical excursions, and kids’ thematic arts and crafts (e.g., building their own Mayflower models). Easily 5-10 hours of work if I hadn’t used AI.
Zac: For legal teams exploring AI or automation for the first time, what’s the best “low-risk, high-impact” place to start?
Jacob: Two starting points:
(1) What repeated tasks frustrate you or your legal team? Start with repeated tasks that make you or your team think: this isn’t what I went to law school for.
(2) If supporting a commercial function, ask the sales team. Sales will give direct feedback on what’s working and what isn’t.
As you use AI, it’s helpful to remember this framework: think of AI as “middle to middle” and not “end to end.” Humans provide the context and effective prompt (the start), let the AI process (middle to middle), and then humans verify and refine the output (the end). More from Balaji S. Srinivasan: AI is polytheistic, not monotheistic – balajis.com.
Zac: What AI tools do you currently use?
Jacob: Work: gc.ai and Practical Law AI features.
Personal: ChatGPT, Lovable for “vibe coding” kids’ games and other silly projects, and Rufus on Amazon for selecting products.
Advice for Aspiring and Current Legal Leaders
Zac: What advice would you give to GCs who are new to the role or aspiring to that seat?
Jacob: First, speak the language of your business partners. Frame guidance in business terms, with explicit trade-offs and impact on growth, margin, and risk, not in isolated legal concepts.
Second, remember the puzzle analogy. You’re not executing on your legal pieces, divorced from a broader picture. You’re helping to shape, design, and combine the pieces so the company can accomplish its strategic objectives. That’s the real value creation. It also means keeping your board and leadership aligned on the picture and any major one-way doors ahead.
Third, embrace uncertainty. Don’t bet on your ability to predict the future. Build for optionality and flexibility. Move fast on two-way doors. Be rigorous and intentional about one-way doors.
Fourth, start using AI now. Don’t wait. Start in your personal life if you need to, but build that muscle. Lawyers who embrace AI will thrive.
And finally, remember your role: help the business accomplish its objectives. If you’re not doing that, you’ve lost the plot.
Thanks, Zac. I enjoyed the discussion.
Organizations and Tools Mentioned
gc.ai – AI copilot purpose-built for in-house counsel, generating high-quality drafts, legal research, and advice.
Practical Law (Thomson Reuters) – Legal know-how and drafting resources with integrated AI features.
ChatGPT (OpenAI) – General-purpose AI assistant with reasoning capabilities.
Lovable – Platform for rapid prototyping and “vibe coding” simple applications.
