Head of Finance

About Fulcrum

Think about everything that matters to you — your home, your car, your business, your team. Almost all of it is insured. Now think about how much of that industry still runs on spreadsheets and email.

Insurance is one of the largest service verticals in the world — a $1.5 trillion industry that touches every business and every person. Every business has it. Most people never think about it. That's exactly why the software opportunity is so large.

Software has transformed finance, healthcare, logistics, and real estate. Insurance is the last major services vertical where AI hasn't rewritten the rules yet. We're changing that.

We're building the AI platform for insurance brokers — the firms that sit at the center of this industry and service the biggest companies in the world. Our platform automates the work that used to eat up entire teams, saving our customers thousands of hours and millions of dollars every year. We're post-Series A, already trusted by 30% of the top 50 brokers in the country, and growing fast. The largest players in the space aren't just our customers — they're our advocates.

Most people spend their careers in markets that are already well-served. This isn't that — and we're just getting started.

Why Fulcrum

• Rocket-ship growth. We've achieved multiple seven figures in ARR in just over a year, serving large enterprise clients including 30% of the top 50 brokers in the country.

• Extreme ownership. You'll be our first finance hire, with full latitude to build the function from the ground up.

• Real stakes, real impact. We're attacking one of the largest untapped verticals in the world. Your work will directly shape how we deploy capital, communicate with investors, and scale into our next phase of growth.

• World-class people. We hire exceptionally — every person on this team is among the best at what they do. You'll be surrounded by people who raise your game.

• In-person collaboration. Join a lean, staff-level team (ex-Affirm, Uber, DoorDash, McKinsey) working side-by-side in San Francisco; we believe the best ideas are fostered in an in-person environment.

• Massive upside. Competitive base salary plus meaningful founding-team equity.

About the Role

We're seeking a Head of Finance to build our finance function from scratch. As our first finance hire, you won't inherit a playbook—you'll write it. You'll assess where we stand, decide what to build, and then build it: accounting infrastructure, FP&A, tax and compliance, and investor relations. You'll start as a team of one—hands-on across everything—and grow the function by hiring and developing a team as the company scales. This role is for someone who thrives in ambiguity, moves fast, and can zoom between month-end close and board-level storytelling. You'll report directly to the CEO and sit at the table for our most consequential decisions.

What You'll Do

• Investor Relations. Own the investor relationship end-to-end — board materials, quarterly updates, cap table hygiene, and 409A valuations. Be the connective tissue between our financial story and the people who believe in it.

• Fundraising. Lead financial preparation for future raises: data room, diligence, financial narrative, and coordination with outside counsel. Partner closely with the CEO to get us across the finish line.

• Financial Strategy. Build and own our financial models, forecasts, and budgets. Fluent in SaaS metrics — ARR, NRR, CAC, LTV — and able to translate them into decisions that shape the company.

• Cash & Capital. Own cash management and burn tracking. Keep leadership informed and ahead of the curve; help us think clearly about capital allocation and headcount.

• Accounting Infrastructure. Establish the accounting processes, controls, and systems to scale — monthly and quarterly close, financial statements, ASC 606 revenue recognition, and audit readiness.

• Tax & Compliance. Oversee federal, state, and local obligations including sales tax nexus and R&D tax credits. Know when to go deep yourself and when to bring in outside expertise.

• Operations. Manage payroll, benefits administration, AP, vendor relationships, and banking — building the operational backbone until we have the team to hand these off.

• Team Building. You start as a team of one. As we grow, you hire and develop the finance team beneath you — and define what great finance talent looks like at Fulcrum.

What You'll Bring

• 8+ years of finance experience, with a mix of accounting, FP&A, and investor-facing work.

• Evidence that you can build, not just operate — whether that's standing up a finance function, leading a fundraise, creating structure where there was none, or taking on scope well beyond your job title.

• Demonstrated ability to hire and develop finance talent as the company grows.

• Strong command of GAAP, ASC 606 revenue recognition, financial modeling, and board-level reporting.

• Fluent in SaaS metrics and able to build the reporting infrastructure around them.

• Experience supporting or running a fundraise (Series A and beyond), including working with outside counsel on financing and equity documents.

• Comfortable owning tax, compliance, payroll, and equity administration — and knowing when to bring in outside expertise.

• An independent mind. You form views from first principles, push back when you disagree, and don't wait to be told what needs to be done. You're as comfortable making the call as you are doing the work.

• Exceptional communication skills; able to translate complex financials into clear narratives for founders, investors, and operators.

• CPA or MBA a plus, but not required if your experience speaks for itself.

• Ability to work 5 days a week from our San Francisco office (open to candidates willing to relocate).

Our Team and Philosophy

• Builders at heart. You don't wait for a process to exist—you create it, refine it, and own it.

• Bias toward action. You have an internal sense of urgency. You'd much rather get something done today than tomorrow.

• Owners, not renters. You treat the company's money and decisions like your own. You hold yourself accountable to outcomes, not just outputs.

• Ambitious about the opportunity. You're excited about building the defining AI company in the insurance industry—and you understand that great finance is a competitive advantage.

What We Offer

• Competitive salary + meaningful equity.

• Full health, dental & vision.

• High-ownership, high-trust culture with lightning-fast executors.

• Regular team off-sites, dinners, and an office stocked for builders.