Head of Operations & Strategy - Remote & AI-Driven Growth

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

Benefits offered by this job

Health insurance

Retirement plan with employer match

Paid time off and parental leave

Wellness reimbursement and remote work

Job summary

Swooped is seeking a Head of Operations and Strategy to align organizational strategy with execution. The role reports to the General Manager of Insurance and sits on the executive team, leading ~15 people across Operations, Marketing, Safety, and Insurance Ops.

The role is full-time in the United States with work-from-home flexibility, shaping cross-program priorities, operating rhythms, and critical initiatives. Requires extensive strategy-to-execution experience and strong analytical skills.

Qualifications

• 10–15+ years of experience in strategy, operations, management consulting, or general management.
• Experience operating across the complete strategy-to-execution lifecycle.
• Advanced analytical capabilities including financial modeling, unit economics, P&L analysis, and data-driven business cases.
• Proven track record leading multidisciplinary teams of 10–20+ people.
• Experience establishing operating cadences, planning frameworks, and accountability systems.
• Strong executive presence and written communication skills.
• Ability to manage ambiguity and prioritize high-impact strategic initiatives.

Responsibilities

• Define annual and quarterly planning cycles with FP&A and translate objectives into priorities and resource allocation.
• Monitor performance with data-driven analyses and root-cause assessments.
• Advise on partnerships with carriers and reinsurers, with rigorous evaluation.
• Scale learnings across units by implementing scalable practices.
• Evaluate growth opportunities, build business cases for go/no-go decisions.
• Direct operating cadences: leadership meetings, reviews, planning sessions, board prep.
• Ensure infrastructure, systems, reporting, and tooling to scale programs.
• Drive automation and AI initiatives and measure outcomes.
• Guide marketing to connect strategy to measurable pipeline results.
• Oversee safety programs to inform data-driven decisions.
• Partner with GMs and functional heads as analytical counterpart.
• Drive cross-functional initiatives spanning org boundaries.
• Mentor and develop a multidisciplinary team with high standards.
• Develop executive dashboards and communication frameworks for visibility.

Skills

Strategic planning

Financial modeling

Data analysis

Leadership

Executive communication

Change management

Ambiguity management

Job description

Swooped is seeking a Head of Operations and Strategy to align organizational strategy with execution. The role reports to the General Manager of Insurance and sits on the executive team, leading ~15 people across Operations, Marketing, Safety, and Insurance Ops.

The role is full-time in the United States with work-from-home flexibility, shaping cross-program priorities, operating rhythms, and critical initiatives. Requires extensive strategy-to-execution experience and strong analytical skills.