[Remote] Head of Operations and Strategy

Note: The job is a remote job and is open to candidates in USA. Nirvana Insurance is a commercial insurance company using AI and real-time IoT data to improve risk assessment and insurance operations. The Head of Strategy & Operations sets strategic priorities, leads operating processes and cross-functional initiatives, and oversees teams across business operations, marketing, safety, and insurance operations.

Responsibilities

• 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
• 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
• 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

Skills

• 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
• 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

Benefits

• Equity
• Medical, dental & vision insurance (100% employer paid)
• 401k with up to 4% company match
• Unlimited PTO
• Parental leave
• Wellness reimbursement
• Work from home friendly
• Work-from-home stipend

Company Overview

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