Head of Operations and Strategy

This is a fully remote position, open to applicants in United States.

📋 Description

• Define and lead the annual and quarterly planning process in collaboration with FP&A.

• Convert long-term vision into actionable priorities, OKRs, and decisions regarding resource allocation.

• Track business performance and conduct in-depth analyses to identify root causes.

• Provide guidance on partnerships with carriers and reinsurers.

• Facilitate cross-program learning and share insights across business units.

• Assess growth opportunities and create business cases for go/no-go decisions.

• Manage weekly leadership routines, monthly business reviews, quarterly planning cycles, and board preparations.

• Oversee the business operations function and establish scalable systems, processes, reporting, and tools.

• Replace manual tasks with AI agents and automation while measuring their impact.

• Enhance marketing efforts across demand generation, branding, content, and go-to-market enablement.

• Lead and expand safety programs and interventions for fleet operations.

• Collaborate with program GMs and functional leaders on key decisions.

• Spearhead high-priority company-wide initiatives that lack a designated owner.

• Build, attract, develop, and manage a high-performing cross-functional team.

• Create dashboards, reporting mechanisms, and communication frameworks for enhanced leadership visibility.

• Mentor and coach top talent.

⛳️ Requirements

• 10-15+ years of experience in strategy, operations, consulting, or a general management role.

• Proven ability to navigate the complete strategy-to-execution continuum.

• Proficiency in financial modeling, unit economics, and data-driven decision-making.

• Capability to analyze a P&L and formulate a business case.

• Experience in leading and developing teams of 10-20+ individuals across various functions.

• Strong, well-founded opinions on operational cadences, planning rhythms, and accountability systems.

• Executive presence along with outstanding written communication skills.

• Ability to prepare for board meetings, draft decision memos, and present to stakeholders.

• Comfort in uncertain situations and a keen ability to prioritize effectively.

• 3+ years at a high-growth organization where you have contributed to building operational infrastructure from early stages to scale (preferred).

• Experience in the insurance or insurtech sector, particularly in P&C, commercial auto, or MGA operations (preferred).

• Background in management consulting (MBB or equivalent) or corporate development (preferred).

• Experience in developing or implementing AI/automation in operational workflows (preferred).

• Familiarity with telematics, IoT data, or data-driven underwriting models (preferred).

• Leadership experience in marketing and knowledge of marketing technology stacks and scaled B2B marketing operations (preferred).

🏝️ Benefits

• Competitive salary & equity.

• Comprehensive medical, dental & vision insurance (100% employer paid).

• 401k plan with up to 4% company match.

• Unlimited paid time off.

• Parental leave benefits.

• Wellness reimbursement program.

• Flexible work-from-home policy.

• Work-from-home stipend.

• Paid time off.