We're looking for a Senior Manager to fundamentally reshape how insurance filings get done at Lemonade. This role sits at the intersection of AI platform design, regulatory operations, and change leadership — and you'll own it end to end, working closely with our Product, Engineering, Actuarial, and Compliance teams inside Insurance Operations.
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’llLead filing platform and automation initiatives from concept through rollout — scoping, building, testing, and iterating in close partnership with Product and Engineering
Map filing workflows and regulatory requirements continuously to identify the highest-impact opportunities for AI integration, automation, and systemic efficiency gains
Drive adoption of new tools and workflows across the insurance org, translating platform capabilities into clear value for stakeholders
Build and lead the IO platform team focused on owning and scaling filing tooling, fostering a culture where experimentation, regulatory credibility, and operational impact are equally valued
Set and hold the bar for filing quality, speed, and compliance as automation takes on more of the work — ensuring what gets built performs in a regulated environment
Establish the operating model, governance, and feedback loops that let the platform team build with speed and rigor
6+ years in insurance, with meaningful exposure to filings, regulatory operations, or compliance
3+ years leading teams, with a track record of managing technically strong ICs and holding them accountable to outcomes
Direct experience with automation and process improvement, required
Experience identifying manual or inefficient operational workflows and replacing them with technology-enabled solutions that improve speed, accuracy, and cost efficiency
Hands-on fluency with LLMs like Claude or ChatGPT — you know how to build prompts, map logic, and use AI to multiply your output, not just talk about it
Strong project management and stakeholder communication skills: you move work forward through others, translate between technical and operational, and don't lose momentum when priorities shift
Advanced data analysis skills and the ability to independently extract insights that drive platform decisions
A builder's mentality: energized by ambiguity, focused on outcomes, and comfortable creating structure where there isn't any
*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 $130,000 - $152,500 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. Our competitive total rewards package includes comprehensive health & wellness coverage, equity, a 401(k) plan with employer match, 20 paid vacation days, and parental leave. Speak to your recruiter to hear more about the specific salary range for your preferred location and our total rewards package.
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Skills Required
- 6+ years in insurance with exposure to filings, regulatory operations, or compliance
- 3+ years leading teams and managing technically strong individual contributors
- Direct experience with automation and process improvement
- Experience replacing manual operational workflows with technology-enabled solutions
- Hands-on fluency with LLMs (e.g., Claude, ChatGPT); prompt building and logic mapping
- Strong project management and stakeholder communication skills
- Advanced data analysis skills and ability to extract independent insights
- Builder's mentality: comfortable with ambiguity and focused on outcomes
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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