Automation Engineer, Billing Platform

What You’re Applying For We're looking for an Automation-First QA Engineer to help us build quality into the Billing Platform from the ground up. This role sits at the intersection of engineering, automation, and AI — and it's core to how our Engineering team ships fast without breaking things. You'll own quality strategy for your domain and shape the tools, frameworks, and systems that let developers and AI agents move at full speed.

We believe three things matter for every role at Lemonade: drive to push through challenges, efficiency that keeps standards high while moving fast, and adaptability that lets you pivot with data and AI insights. 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

• Own quality strategy for the Billing Platform — setting the vision while empowering developers to lead day-to-day quality in their code
• Build and evolve automated testing solutions across Web, API, and end-to-end user flows
• Design tools, frameworks, and infrastructure that make quality faster, more scalable, and more autonomous
• Use AI agents and prompt engineering to improve test creation, coverage analysis, and other parts of the quality lifecycle
• Partner with developers, Product, and Design to surface risks early and influence technical decisions before they become costly ones
• Translate quality data and delivery signals into clear recommendations on gaps, priorities, and readiness
• Drive quality engineering best practices across the organization — not just within your own domain

What You'll Need

• 4+ years of experience as a QA Engineer or Software Engineer in Test
• Strong coding skills in at least one modern language — TypeScript, Python, or similar
• Hands-on experience with Playwright, Cypress, or comparable modern automation frameworks
• Experience designing end-to-end testing strategies across Web, API, and data layers
• A builder mindset — you turn ideas into tools and frameworks, not just test cases
• A red team instinct — you challenge assumptions, stress-test decisions, and find the edge cases others miss
• Familiarity with AI tools, prompt engineering, or AI agents, and genuine curiosity about where they take software quality next
• Excellent written and verbal communication skills in English
• Ready to work in an office environment most days of the week

Things to know…

Lemonade is an equal opportunity employer committed to diversity and inclusivity. We never discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status. If you require reasonable accommodations due to religious beliefs, pregnancy, or disabilities, let us know at any time.