We're looking for a Senior Director of Engineering to help scale how we build and own the core of Lemonade's business. This role sits at the center of our R&D organization, partnering closely with senior product and tech leadership to raise the bar on engineering culture, team structure, and platform ambition.
We believe two things matter for every leadership role at Lemonade: leadership that sets the bar for excellence, builds high performing teams, and holds them accountable, and strategy that thinks several years ahead and turns ambitious plans into reality. 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.
Lead multiple engineering domains, owning the structure, standards, and performance of teams that build Lemonade's core product
Drive strategic initiatives that increase engineering leverage, so we can do more with smaller, sharper teams
Partner with senior product and tech leaders to shape how we build, not just what we build
Architect next-generation platforms that support our evolving product vision and scale with the business
Attract, develop, and retain high-performing engineers, holding a high bar at every stage of the hiring and growth process
Turn complex business problems into technical solutions that are clean, scalable, and built to last
Embed AI into how we develop and ship, using it to accelerate delivery and raise the quality ceiling
Experience scaling high-performing engineering organizations through fast-growth phases, with a track record of raising the bar on delivery and quality
A leadership style that sets high standards, leads by example, and creates accountability without losing the team
Comfort operating in a product-led environment, where engineering and product move together
Strong communication skills, with the ability to give direct feedback, recognize great work, and build trust across levels
A genuine belief in meritocracy, where hiring and growth decisions are driven by skill, performance, and motivation
A bachelor's degree in Computer Science, Software Engineering, or a related technical field
Ready to work in an office environment most days of the week
Skills Required
- Experience scaling high-performing engineering organizations through fast-growth phases
- Proven leadership style that sets high standards, leads by example, and creates accountability
- Comfort operating in a product-led environment with close engineering-product collaboration
- Strong communication skills, including giving direct feedback and building cross-level trust
- Belief in meritocracy driving hiring and growth decisions
- Bachelor's degree in Computer Science, Software Engineering, or a related technical field
- Willingness and ability to work in an office environment most days of the week
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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