Head of Finance

WHO WE ARE

The company is on a mission to harness the power of data to revolutionize commercial insurance and enable a safer world. We are bringing much-needed innovation into the legacy, trillion-dollar commercial insurance industry. We have developed cutting-edge predictive models that use real-time IoT data from billions of connected devices, allowing us to better understand and price risk. Our AI-driven platform fundamentally changes the way an insurance company operates with personalized risk scoring, faster underwriting, modernized claims, and proactive, data-driven insights to help customers prevent accidents.

We’ve already proven the scale—serving thousands of fleets and more than doubling our written premiums year over year. Our data moat is growing exponentially with more than 30 billion miles of telematics data, leading to more predictive models and new insights into how we can better understand and reduce risk. Altogether, our loss ratio, efficiency, and customer experience are redefining what can be done in the industry.

With $270+ million raised, including our Series D round in December 2025, we’re only accelerating our growth, with strong support from top-tier VCs including Lightspeed, General Catalyst, and Valor. The company’s leadership team has previously helped scale multi-billion-dollar companies from scratch, including Samsara, Glassdoor, and Flexport, and includes industry veterans from Nationwide, The Hartford, and RLI.

ABOUT THE ROLE

In this role, you'll be the financial owner of the company Insurance Services (NIS), a commercial insurance MGA and the engine of our written premium growth. You'll own its accounting close, revenue recognition, billing operations, reinsurance program economics, and business-unit FP&A end to end.

Today that work sits across several people as one piece of each of their broader, multi-entity roles. As we scale, NIS deserves a single, accountable owner — and this is that seat. You'll report to our CEO, oversee our Accounting, Billing, and FP&A teams, and partner closely with our cross-functional leaders across the company.

This is a high-impact, high-autonomy role for someone who thrives in a fast-paced, ambiguous environment. You'll build and enhance the processes, source of truth, and the team behind one of the most economically important parts of the company.

WHAT YOU'LL DO

• Own NIS's monthly, quarterly, and annual FP&A cycle — budget-vs-actual for the company and its programs — and author the variance narrative that feeds our board process

• Own NIS's accounting close and revenue recognition for MGA commission income (ASC 606), including treaty-year commission-rate reconciliation

• Own NIS's billing operations — premium invoicing, mileage-based installment billing, agency commission netting — across all insurance programs, partnering with the Billing team on execution and serving as the escalation point for billing disputes and cancellations

• Own premium trust account funding approval and serve as the escalation point for fronting-carrier remittance operations, partnering with our Controller's team on execution

• Own the reconciliation of NIS's reinsurance program economics — quota share loss ratios and provisional and contingent commission true-ups by treaty year — and build the single, shared source of truth behind them

• Own financial oversight of our subproducer and agency agreements, from reviewing terms to resolving remittance and commission-balance questions with our agency partners

• Coordinate NIS's audit deliverables with our external auditors as part of the broader company-wide engagement

• Author NIS's financial narrative and results for the board deck

• Serve as the day-to-day financial partner to our Fleet, Business Auto, and Non-Fleet business-unit leads

• Build and lead a small, high-leverage team, with an accountant, FP&A lead, and billing operations associates

ABOUT YOU

• Hands-on experience across both accounting and finance/FP&A inside an operating company of approximately 8 - 12 years

• Detail-oriented and execution-focused, with the resilience to thrive in a high-performance, fast-paced setting

• Hands-on operator: comfortable digging into the details with teams, implementing solutions, and iterating quickly — not just producing metrics or analysis

• Comfortable operating in an environment where entity structures and processes can be complex and navigating those challenges and building the future is energizing

• Demonstrated outstanding analytical and problem-solving skills

• Excellent communication skills with the ability to simplify and articulate complex financial concepts to diverse stakeholders, from executives to operators

• ASC 606 revenue recognition experience, ideally with commission-based revenue models

• Prior experience in fintech; some fluency in insurance or MGA economics are nice to have experience

• Experience overseeing billing or invoicing operations is a plus

• Prior insurance or financial services experience is a nice to have, not a requirement

BENEFITS

• Competitive salary & equity

• Medical, dental & vision insurance

• 401k with company match

• Unlimited PTO

• Remote (U.S.)

We set our salary ranges using compensation data from companies similar to our stage and size. For this role, the estimated salary range for this position is $200K - $280K. The actual base salary will vary depending on multiple factors unique to each candidate, including location, job-related knowledge, transferable skills, work experience and our assessment of your level during the interview process.

The company offers a wide range of best-in-class, comprehensive benefits for this role including 100% employer paid healthcare plans, a healthy 401k match program, paid time off, parental leave, wellness reimbursement, work-from-home stipend and more. In addition, the company offers equity for all full-time employees, which is not included in the range listed above and will have a significant impact on your overall compensation.

The company is committed to building a diverse and inclusive workforce. If you're interested in this role, but do not meet 100% of the qualifications listed above, we encourage you to apply. We'd like to consider you for this position and roles that may be a fit in the future. The company is an Equal Opportunity Employer and considers applicants for employment without regard to race, color, religion, sex, orientation, national origin, age, disability, genetics or any other basis forbidden under federal, state, or local law. The company considers all qualified applicants in accordance with the San Francisco Fair Chance Ordinance.