Senior Director of Engineering

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.

In this role you'll:

• 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

What you’ll need:

• 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