Senior Operations Manager, Strategy & Insights

Summary

Join Lemonade's Customer Operations enablement team as a high-impact leader, steering cross-departmental initiatives across Claims, Underwriting, and CX teams. You will combine strategic planning with operational leadership, redesigning processes, strategizing vendor relationships, and implementing automation. Partnering with various teams, you'll translate insights into scalable, tech-enabled solutions. You'll report to the Director of Operations and manage an Operations team. This role demands strong analytical, communication, and leadership skills, with a passion for AI-driven automation. The position offers a competitive salary, equity, healthcare benefits, 401(k), PTO, and parental leave.

Requirements

• 4+ years in strategy, operations, consulting, or program management—experience in tech/SaaS or high-growth environments preferred; P&C insurance a plus
• Proven success leading complex, cross-functional initiatives from concept through measurable results
• Fluency with data: SQL/BI tools, financial modeling, and the ability to translate metrics into business decisions
• BA Degree in Analytics or related field
• Passion for AI-driven automation and a track record of operational innovation
• Executive-level communication skills—able to distill complexity, influence decisions, and drive alignment across levels and functions
• Ability to work 100 % remotely
• Enthusiasm about learning and adapting to the exciting world of AI – a commitment to exploring this field is a fundamental part of our culture

Responsibilities

• Own the strategy cadence for Customer Ops—defining objectives, road-mapping initiatives, and tracking progress against cost and quality KPIs
• Lead cross-functional projects that streamline workflows, expand automation, and unlock efficiency across Claims, Underwriting, and CX
• Build executive-ready business cases using rigorous financial analysis and forecasting to influence budgeting and headcount decisions
• Translate data into action—partner with Analytics to surface insights and with Product to embed them in tooling and platform enhancements
• Develop and execute a holistic vendor strategy covering selection, onboarding, relationship management, and ongoing optimization to maximize value
• Rally stakeholders around change—craft crisp narratives, socialize proposals, and ensure smooth execution from pilot through scale
• Mentor and develop a lean team of high-caliber operators and analysts, fostering growth and high performance

Benefits

• Access to healthcare benefits
• 401(k) plan with company match
• Robust PTO
• Parental leave