Head of Operations and Strategy

Swooped; United States; Hybrid; USD 280,000 - 370,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

Equity compensation

Retirement plan with employer match

Paid time off and parental leave

Wellness reimbursement and remote work

Job summary

Swooped, a United States-based company, is seeking a Head of Operations and Strategy to align organizational strategy with execution across Business Operations, Marketing, Safety, and Insurance Operations. The role reports to the General Manager of the Insurance business and sits on the executive leadership team.

The position offers full-time work with work-from-home flexibility, and you will shape cross-program priorities, establish scalable operating rhythms, and lead cross-functional

Qualifications

• 10+ years in strategy, operations, or general management.
• Experience across strategy-to-execution lifecycle.
• Advanced analytics including P&L, unit economics, financial modeling.

Responsibilities

• Define annual and quarterly plans with FP&A, align priorities and resources.
• Lead data-driven performance reviews and root-cause analyses.
• Guide partnerships and vendor relationships with analytical rigor.
• Scale learning across units and disseminate best practices.
• Develop business cases for new markets and growth opportunities.
• Lead executive cadences: leadership meetings, reviews, and board prep.
• Ensure operational infra, systems, and tooling scale programs.
• Drive automation and AI initiatives in workflows.
• Guide marketing to connect strategy with measurable pipeline.
• Oversee safety programs and data-informed decisions for fleets.
• Collaborate with GMs and heads as analytical counterpart.

Skills

Strategic planning

Analytical thinking

Financial modeling

Leadership

Executive communication

Job description

The hiring organization is seeking a Head of Operations and Strategy to lead the alignment between organizational strategy and execution. Reporting directly to the General Manager of the Insurance business and serving on the executive leadership team, this leader will guide an organization of approximately 15 people spanning Business Operations, Marketing, Safety, and core Insurance Operations.

This is a full-time role based in the United States with work-from-home flexibility, operating at the center of company decision-making to shape cross-program priorities, establish scalable operating rhythms, and lead critical cross-functional initiatives.

Key Responsibilities

• Define and lead the annual and quarterly planning cycles in partnership with FP&A, translating strategic objectives into concrete priorities, OKRs, and resource allocation decisions across business lines.
• Monitor and evaluate business performance against plans, conducting deep dives and root-cause analyses to maintain a data-driven understanding of performance trends.
• Advise on key partnership strategies, including carrier and reinsurer relationships, bringing analytical rigor to evaluation, structuring, and ongoing management.
• Lead cross-program learning by identifying successful practices within individual business units and building mechanisms to scale those insights organization-wide.
• Evaluate new growth opportunities, such as new markets, adjacent lines, and distribution strategies, developing business cases to guide go/no-go decisions.
• Direct operating cadences at scale, including weekly leadership meetings, monthly business reviews, quarterly planning sessions, and board preparation.
• Lead the business operations function to ensure programs have the operational infrastructure, systems, reporting, and tooling needed to scale efficiently.
• Drive the core operations agenda by identifying opportunities to replace manual processes with automation and AI agents, prioritizing development, and measuring outcomes.
• Guide and scale the marketing function across demand generation, brand, content, and go-to-market enablement to connect strategy to measurable pipeline results.
• Oversee and scale safety programs and interventions designed to help commercial fleets make data-informed decisions.
• Partner with program General Managers and functional heads as an analytical counterpart to guide strategic decisions.
• Drive high-priority, cross-functional initiatives that span organizational boundaries without a dedicated functional owner.
• Attract, develop, and mentor a multidisciplinary team, maintaining high talent standards and fostering professional growth.
• Guide the development of executive reporting dashboards and communication frameworks that provide clear performance visibility.

Required Qualifications

• 10 to 15+ years of experience in strategy, operations, management consulting, or a general management role.
• Demonstrated experience operating across the complete strategy-to-execution lifecycle, including setting strategic direction and establishing the teams and processes to execute against it.
• Advanced analytical capabilities, including fluency in financial modeling, unit economics, P&L analysis, and data-driven business case development.
• Proven track record of leading and developing multidisciplinary teams of 10 to 20+ people.
• Demonstrated experience establishing operating cadences, planning frameworks, and accountability systems that drive sustained organizational alignment.
• Strong executive presence and written communication skills, with demonstrated experience preparing board materials and executive decision memos.
• Demonstrated ability to manage ambiguity, exercise judgment, and prioritize high-impact strategic initiatives.

Preferred Qualifications

• 3+ years of experience in a high-growth environment building operational infrastructure from early stage through scale.
• Industry experience in insurance or insurtech, particularly within property and casualty (P&C), commercial auto, or managing general agent (MGA) operations.
• Background in management consulting at a premier firm or corporate development.
• Direct experience building or deploying AI and automation within operational workflows.
• Familiarity with telematics, IoT data, or data-driven underwriting models.
• Marketing leadership experience, including designing or implementing marketing technology stacks within a scaled B2B environment.

Compensation and Benefits

• Estimated total cash compensation: $280,000 - $370,000. Actual base salary varies depending on candidate location, job-related knowledge, transferable skills, and interview assessment.
• Equity compensation is provided for full-time roles.
• Comprehensive health, dental, and vision insurance.
• Retirement plan with employer match.
• Paid time off and parental leave.
• Wellness reimbursement and remote work support.

Equal Opportunity and Notices

The hiring organization is an Equal Opportunity Employer and considers applicants for employment without regard to race, color, religion, sex, sexual orientation, national origin, age, disability, genetics, or any other basis protected under federal, state, or local law.

All qualified applicants will be considered in accordance with the San Francisco Fair Chance Ordinance. Candidates who are interested in the role but do not meet every single qualification are encouraged to apply.