We're looking for a Senior Operations Manager to lead AI-powered automation across Lemonade's Customer Operations organization — and fundamentally change how we serve customers at scale.
This isn't an oversight role. It's a builder role. You'll own the automation strategy across CX, Claims, and Underwriting, sitting within our centralized Customer Operations team, partnering daily with Product and Engineering to shape the roadmap and drive our AI-first operational transformation from concept through production scale.
We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. These aren't buzzwords, they're how we actually work.
Our AI-first approach isn't just a tagline either. We're building the future of insurance with AI at the center, and we need people who are genuinely excited to learn and grow alongside these tools.
In this role you'll
Own the automation roadmap across Customer Ops — setting priorities, defining requirements, and driving delivery of AI-powered solutions across digital CX, Claims, and Underwriting workflows in close partnership with Product and Engineering
Serve as the primary ops-side counterpart to Product on GenAI programs, shaping how automation solutions are built, tested, and operationalized — and closing the feedback loop so what gets built actually works in production
Build hands-on — designing agent architectures, engineering prompt workflows, and vibe-coding automation tools. You're not just managing builders; you are one
Build executive-ready business cases with rigorous financial analysis and forecasting that influence budgeting, headcount, and automation investment decisions
Lead and develop a team of builders focused on GenAI integration and workflow automation, fostering a culture where experimentation, technical craft, and operational impact are equally valued
Drive GenAI initiatives from pilot to production — owning the full lifecycle from proof-of-concept through scaled deployment across CX, Claims, and Underwriting
Champion an AI-first mindset across Customer Ops, setting the pace for how the team thinks about automation and keeping the organization on the frontier of emerging tools and techniques
Own the tooling strategy and vendor feedback loop, ensuring operational needs shape tooling decisions through structured feedback, testing, and roadmap input to Product and external partners
What you'll need
6+ years in operations, program management, or a similar role — preferably in technology, insurance, or fintech
3+ years of hands-on experience building AI and automation solutions: prompt engineering, workflow automation, AI agent design, or vibe coding — a portfolio of things you've built, not just programs you've managed
2+ years of team leadership with a track record of developing high-performing individual contributors
Demonstrated ability to partner cross-functionally with Product and Engineering, translating operational needs into technical requirements and driving shared outcomes
Strong data fluency — comfortable with SQL, BI tools, and turning metrics into decisions that stick
Executive-level communication skills — able to distill complexity, influence decisions, and drive alignment across levels and functions
A builder's mindset — you default to building the solution, not writing the requirements doc for someone else to build
A genuine, demonstrated commitment to staying on the frontier of AI tools, techniques, and applications — enthusiasm alone isn't enough
Ability to work in a remote environment
College Degree
Please note that we are unable to sponsor applicants for work visas.
Unfortunately, we cannot consider applicants from these states: Alaska, California, Colorado, Montana, Hawaii, New Mexico and Puerto Rico.
Lemonade's US base salary range for this full-time position is $140,000 - $155,000 plus equity + benefits. Our salary ranges are determined by role, level, and location. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Speak to your recruiter to hear more about the specific salary range for your preferred location.
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Skills Required
- 6+ years in operations, program management, or a similar role (preferably technology, insurance, or fintech)
- 3+ years hands-on experience building AI and automation solutions (prompt engineering, workflow automation, AI agent design, vibe-coding)
- 2+ years of team leadership with a track record of developing high-performing individual contributors
- Demonstrated ability to partner cross-functionally with Product and Engineering and translate operational needs into technical requirements
- Strong data fluency, comfortable with SQL and BI tools, and turning metrics into operational decisions
- Executive-level communication skills to distill complexity and influence cross-functional stakeholders
- Builder's mindset with hands-on execution (designing agent architectures, engineering prompt workflows, building automation tools)
- Demonstrated commitment to staying on the frontier of AI tools, techniques, and applications
- Ability to work in a remote environment
- College degree
Lemonade Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Lemonade and has not been reviewed or approved by Lemonade.
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Healthcare Strength — Health coverage is delivered via mainstream Cigna medical options, with multiple plan types and supplemental health protections. This signals broad networks and a robust core healthcare offering.
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Retirement Support — A company 401(k) match is part of the package and is positioned alongside other core financial benefits. This provides structured retirement savings support as a standard element of total rewards.
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Leave & Time Off Breadth — PTO is presented as generous, alongside paid sick time and strong parental leave with a return-to-work program. These time-off provisions extend beyond the basics and support work-life needs.
Lemonade Insights
What We Do
Our mission is simple: Create the world’s most loved insurance through technology and social impact. As a certified Public Benefit Corporation and B-Corp, Lemonade is constantly challenging how the insurance industry does business. We’re creating an experience that is fast, affordable, and hassle-free across renters, homeowners, pet, life and car insurance. And through our annual Giveback program, in which leftover premiums are donated to charities our customers choose, we’ve donated nearly $5 million to a variety of organizations in need.
Why Work With Us
We’ve set out to make insurance loveable, fast, simple, and socially impactful - words that aren’t often associated with this industry. We’re a Certified B-corp, the only US insurance company to never invest in polluting industries, and our annual Giveback program has donated nearly $5 million globally to nonprofits in need.
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