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 work across the company to unpack complex problems, spot where technology creates real leverage, and lead a team that turns those opportunities into working solutions, from AI agents and automation to custom builds, integrations, and enterprise platforms.

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

• Get deep into how teams operate, understanding their goals, economics, workflows, and constraints to identify the highest-leverage opportunities for technology

• 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 framing the problem and shaping the solution through implementation, adoption, and measurable impact

• 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

• Build a point of view on where technology creates the most leverage across Lemonade, then turn that into a portfolio of initiatives you drive from opportunity to measurable impact

What you'll need

• 7+ years leading complex technology initiatives, ideally in consulting, digital transformation, or a client-facing environment where you've owned both the problem and the outcome

• Exceptional structured problem solving, you can quickly understand how a business or function works and what drives its outcomes, break down ambiguous problems, and identify where technology can create the most leverage

• Strong technical fluency across architecture, APIs, integrations, data, and automation, enough to shape solution design, evaluate tradeoffs, 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 leading complex technology initiatives from problem definition and solution design through implementation, adoption, and measurable business impact

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

• Strong executive communication and stakeholder management, you can turn complexity into a clear point of view, influence senior leaders, and drive decisions across functions

• A college degree in a relevant field

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