Senior Manager, Insurance Operations

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’LL

- Lead 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

WHAT YOU’LL NEED

- 6+ years in insurance, with meaningful exposure to filings, regulatory operations, or compliance

- 3+ years leading teams, with a track record of managing technic...