Head of Operations and Strategy

Job Description

Who We Are:Nirvana 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. Nirvana's leadership team has previously helped scale multi-billion-dollar companies from scratch, including Samsara, Rubrik, and Flexport, and includes industry veterans from Hiscox, The Hartford, and RLI.

About the Role:We're hiring a Head of Strategy & Operations to own the connective tissue between where Nirvana is going and how we get there. In this role, you’ll help set the strategic direction for our organization, translate that into how we operate, and then build the machinery to execute it.

Leading a ~15 person organization that spans Business Operations, Marketing, Safety, and core Insurance Operations, you will sit at the center of the company’s decision making. You will shape priorities across programs, design the operating cadences that keep leadership aligned, and drive cross-functional initiatives that don't fit neatly into any one team. On any given week, you might advise on a carrier partnership strategy with a reinsurance partner, redesign how we onboard a new line of business, build the automation playbook that retires manual workflows, or run the QBR that holds the org accountable to its targets.

The right person for this role is part strategist and part operator. You think in systems but ship in sprints. You're as comfortable modeling the unit economics of a new program as you are standing up the team and processes to launch it. You've seen what "good" looks like at a company that's growing fast and have opinions about how to build operating muscle without creating bureaucracy.

This role reports to our GM of the Insurance business, and sits on the executive leadership team. You'd have direct exposure across the full business and a seat in executive-level conversations from day one. It's a high-visibility role for someone who wants to operate at the intersection of strategy and execution.

What You'll DoStrategy

• Define and drive the company's annual and quarterly planning process in close partnership with FP&A, translating long-range vision into concrete priorities, OKRs, and resource allocation decisions across programs.
• Own the pulse on business performance - monitor and evaluate progress versus plans, and lead deep-dives and root-cause analyses to ensure a date-driven understanding of trends
• Advise on key partnerships, including carrier and reinsurer relationships, bringing analytical rigor to how we evaluate, structure, and grow these relationships over time.
• Lead cross-program learning - identify what's working in one business unit and build the mechanisms to transfer those insights to others.
• Evaluate new growth opportunities (new markets, adjacencies, distribution strategies) and build the business cases that inform go/no-go decisions.

Operations

• Own the operating rhythm at scale: weekly leadership cadences, monthly business reviews, quarterly planning cycles, and board preparation.
• Lead the business operations function - the team that ensures our programs have the operational infrastructure (systems, processes, reporting, tooling) to scale without linear headcount growth.
• Drive the core operations agenda: identify where manual work can be replaced by AI agents and automation, prioritize the build, and measure the impact.
• Build and continuously improve the marketing function - demand generation, brand, content, and GTM team enablement - connecting growth strategy to measurable pipeline outcomes.
• Lead and scale our safety programs and interventions to help fleets making better decisions based on Nirvana’s insights

Leadership

• Serve as a counterpart to program GMs and functional leaders - a partner with the credibility and analytical depth to shape decisions across programs.
• Drive high-priority, company-level initiatives that fall in the white space between functions; the projects that are critical but don't have a natural owner.
• Leading a high performing team across functions, including attracting, developing, and managing talent to drive to clear outcomes
• Enable and lead a team to build dashboards, reporting, and communication frameworks that give leadership clear line-of-sight into performance without requiring a standing army of analysts.
• Raise the bar on talent for our organization - bring your experience and passion for building great teams, and lean in to mentor and coach top talent.

What You Bring — Must-Haves

• 10-15+ years of experience in strategy, operations, consulting, or a GM-type role
• Demonstrated ability to operate across the full strategy-to-execution arc: you've set direction AND built the team and processes to deliver against it. A track record of strategy decks alone won't cut it.
• Analytical rigor: you're fluent in financial modeling, unit economics, and data-driven decision-making. You can interrogate a P&L, build a business case, and spot when the numbers don't add up.
• Experience leading and developing teams of 10-20+ people across multiple functions. You hire well, give direct feedback, hold a high-bar for talent, and create environments where strong people want to stay.
• Has strong, tested opinions on how to design operating cadences, planning rhythms, and accountability systems that drive real behavioral change.
• Executive presence and exceptional written communication. You can run board prep, write a killer decision-memo, and present to partners without a script.
• Comfort with ambiguity and the judgment to prioritize ruthlessly. At any given time, there are 30 things that could matter, and you pick the 3 that move the needle.

Nice-to-Haves

• 3+ years at a high-growth company where you've built operating infrastructure from early stage through scale.
• Insurance or insurtech industry experience — particularly in P&C, commercial auto, or MGA operations.
• Background in management consulting (MBB or equivalent) or corporate development.
• Experience building or deploying AI/automation in operational workflows
• Familiarity with telematics, IoT data, or data-driven underwriting models.
• Marketing leadership experience - you've built or helped design a marketing technology stack and helped execute it in a scaled B2B marketing function.

Why Join Nirvana

• Run the operating system of a company redefining an industry. Commercial insurance hasn't changed in decades. We're changing it — and you'll own how we operate as we scale.
• Real authority, not just influence. You'll lead a meaningful organization, make resource allocation decisions, and shape company strategy — not just prepare slides for someone else.
• Work at the intersection of AI and insurance. Our models are the product. Understanding how to operationalize AI — and build an organization that compounds its advantages — is the core challenge of this role.
• Join a leadership team that's done this before. Nirvana's leaders have built billion-dollar companies. You'll be surrounded by people who know what scaling looks like and hold a high bar.

Benefits:

• Competitive salary & equity
• Medical, dental & vision insurance (100% employer paid)
• Parental leave
• Wellness reimbursement
• Work from home friendly

We set our salary ranges using compensation data from companies similar to our stage and size. For this role, the estimated total cash for this position is $280,000- $370,000. The actual total cash 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. If you’re interested in this role, but do not meet 100% of the qualifications listed above, we encourage you to apply. Nirvana considers all qualified applicants in accordance with the San Francisco Fair Chance Ordinance.