Director of Business Technology & AI Ops

We're looking for a Director of Business Technology & AI Ops to help Lemonade turn AI into real results for our business teams. You'll identify high-impact opportunities and lead the delivery of scalable solutions with measurable business outcomes.

As we build a more autonomous, AI-first company, you'll help shape our business technology direction - from enterprise platforms to AI-native solutions—and work across business teams, IT, and Product & Engineering to align the right capabilities and approach for each opportunity.

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

• Partner with Customer Operations and Revenue leaders to understand their goals, economics, and workflows, and shape a technology roadmap focused on measurable business impact.

• Lead the redesign of workflows through AI agents, automation, and software to improve performance and build more autonomous operations.

• Work across business teams, IT, and Product & Engineering to align on the right approach and ownership for each initiative, balancing speed, scalability, cost, and long-term value.

• Lead the business technology and AI initiative portfolio: prioritize opportunities, track investments and ROI, drive adoption, and ensure solutions deliver the expected outcomes.

• Shape the evolution of platforms such as Zendesk, Talkdesk, Twilio, and Revenue applications in partnership with business and technology leaders, identifying opportunities to simplify, consolidate, or introduce AI-native alternatives.

• Build and lead a strong team, defining the capabilities and operating model needed to deliver scalable solutions alongside IT and Product & Engineering.

What you'll need

• 7+ years leading business transformation, technology strategy, or complex cross-functional initiatives, ideally in consulting, business operations, or a tech-driven environment.

• Sharp business instincts and structured problem-solving, with the ability to spot what drives performance in complex operations.

• Hands-on understanding of AI, including large language models, agents, and automation, and how to apply them to real business problems.

• Technical fluency across APIs, integrations, data, and enterprise platforms, enough to evaluate solutions and work well with engineers.

• A track record of taking initiatives from idea to adoption and measurable results, including through teams you don't manage.

• Executive-level communication and stakeholder skills, with the confidence to challenge assumptions and align senior leaders.

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