Director of Business Applications

We're looking for a business-minded, technically strong leader to lead Business Applications at Lemonade and play a key role in building a more autonomous company. You'll lead a team that works across Lemonade to understand complex business challenges and turn them into technology solutions - from AI agents and automation to custom solutions, integrations, and enterprise platforms. Doing this well takes a deep understanding of how the business works and the instinct to spot where technology can create genuine leverage.
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

Turn business challenges into working technology solutions - partnering with leaders across Lemonade to find where AI and automation can materially change how work gets done

Build toward a more autonomous Lemonade by identifying where work can be fundamentally redesigned through agents, AI, and software - then leading the team in making it real

Own problems end-to-end, from getting deep into the business challenge, through implementation, adoption, and measurable outcome

Shape a forward-deployed BizApps model where the team works close to the business, moves quickly, prototypes fast, and shares accountability for results

Lead and grow a strong team that combines business understanding, product thinking, and technical depth - raising the bar for ownership, curiosity, and speed

Set the strategy and technical direction for the platforms, integrations, and data flows that power teams across Lemonade

What you'll need

7+ years leading technology solutions for business applications/operations, with experience managing and developing a team.

Strong business judgment - you can quickly map how a function works, what drives its outcomes, and where technology creates real leverage

Strong technical fluency across architecture, APIs, integrations, data, and automation (enough to evaluate solutions and confidently guide technical decisions)

Hands-on familiarity with modern AI capabilities, including LLMs, agents, and AI-enabled development, and genuine curiosity about where it's headed

A track record of turning complex, ambiguous business problems into solutions with measurable impact

Strong product thinking - you start with the problem, challenge requirements, prioritize by impact, and care whether what you build actually gets used

Experience partnering with senior stakeholders on cross-functional, high-ambiguity problems

A college degree in a relevant field

Ready to work in an office environment most days of the week