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'llGet 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
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
Skills Required
- 7+ years leading technology solutions for business operations
- Experience managing and developing a team
- Strong business judgment and ability to identify technology leverage opportunities
- Technical fluency across architecture, APIs, integrations, data, and automation
- Hands-on familiarity with LLMs, AI agents, and AI-enabled development
- Track record converting complex, ambiguous business problems into measurable solutions
- Strong product thinking and ability to prioritize by impact
- Experience partnering with senior stakeholders on cross-functional, high-ambiguity problems
- College degree in a relevant field
- Willingness 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 — Cigna-administered medical plans provide multiple options (EPO/OAP/OAPIN/HDHP) alongside dental, vision, prescription coverage, disability, and life/AD&D. 2026 plan materials and state notices indicate broad essential health benefits with mainstream networks.
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Retirement Support — A tiered 401(k) match structure is documented, offering meaningful employer contributions when employees save. This complements equity grants/RSUs that are commonly included in total rewards.
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Leave & Time Off Breadth — Employee-reported baselines around defined PTO and company holidays, plus flexible sick time, position time off as a strength. Parental leave is frequently described as generous for the U.S. context, though candidates should confirm current specifics.
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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