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Head of Operations and Strategy

Nirvana Insurance - Remote - Remote - posted 2026-10-19

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Salary: USD 280,000 - 370,000 / annual

Nirvana is a commercial insurance technology company using AI-driven predictive models and real-time IoT telematics data to revolutionize risk scoring, underwriting, and claims. The company has raised $270M+ (Series D in December 2025) and is backed by top-tier VCs including Lightspeed, General Catalyst, and Valor. Leadership includes veterans from Samsara, Rubrik, Flexport, and major insurers. You will serve as Head of Operations and Strategy, reporting to the GM of the Insurance business and sitting on the executive leadership team. You will own the connective tissue between strategic vision and operational execution, leading a ~15-person organization spanning Business Operations, Marketing, Safety, and core Insurance Operations. STRATEGY RESPONSIBILITIES: - Define and drive annual and quarterly planning in partnership with FP&A, translating long-range vision into OKRs and resource allocation decisions - Monitor business performance, lead root-cause analyses, and maintain data-driven understanding of trends - Advise on key carrier and reinsurer partnerships, evaluating and structuring relationships - Identify cross-program learning opportunities and transfer insights across business units - Evaluate new growth opportunities (markets, adjacencies, distribution) and build business cases for go/no-go decisions OPERATIONS RESPONSIBILITIES: - Own the operating rhythm: weekly leadership cadences, monthly business reviews, quarterly planning, and board preparation - Lead the business operations function, ensuring programs have systems, processes, reporting, and tooling to scale efficiently - Drive automation agenda: identify manual work replaceable by AI agents, prioritize builds, measure impact - Build and scale the marketing function (demand generation, brand, content, GTM enablement) connecting strategy to pipeline outcomes - Lead and scale safety programs and interventions for fleet decision-making LEADERSHIP RESPONSIBILITIES: - Serve as counterpart to program GMs and functional leaders with analytical credibility - Drive high-priority, cross-functional initiatives in white-space areas without natural owners - Lead a high-performing team across functions: hiring, developing talent, driving outcomes - Build dashboards, reporting, and communication frameworks for leadership visibility - Mentor and coach top talent, raising organizational talent bar QUALIFICATIONS (MUST-HAVES): - 10-15+ years in strategy, operations, consulting, or GM-type role - Demonstrated ability across full strategy-to-execution arc: setting direction AND building teams/processes to deliver. Strategy decks alone insufficient - Analytical rigor: fluent in financial modeling, unit economics, data-driven decision-making. Can interrogate P&Ls, build business cases, spot numerical inconsistencies - Experience leading and developing teams of 10-20+ people across multiple functions. Strong hiring judgment, direct feedback, high talent bar, creates retention environment - Strong, tested opinions on designing operating cadences, planning rhythms, and accountability systems that drive behavioral change - Executive presence and exceptional written communication. Can run board prep, write decision memos, present to partners without script - Comfort with ambiguity and ruthless prioritization judgment. Can identify 3 needle-moving priorities from 30 possibilities NICE-TO-HAVES: - 3+ years at high-growth company building operating infrastructure from early stage through scale - Insurance or insurtech experience, particularly P&C, commercial auto, or MGA operations - Management consulting background (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: built or designed marketing tech stack and executed scaled B2B marketing function

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