Senior AI Quality Engineer

Roofr

1d•Remote

About The Position

At Roofr, we’re obsessed with our customers. We constantly gather feedback to shape, prioritize, and launch the products they truly need. That’s what makes Roofr’s CRM special. We started by building essential sales tools like aerial roof measurements and digital sales proposals. But when our customers asked for a simple, affordable way to manage and scale their entire businesses, we listened. So, we created a CRM that connects these solutions—along with payments, material ordering, and more—into a seamless, powerful platform. With a clear roadmap ahead, we’re excited to continue expanding and leading the market with innovative products. We have an amazing culture, strong financials, and best-in-class company metrics. It’s an exciting time to be part of an extraordinary startup that is already successful, yet still early enough to offer its team significant growth, equity, and the opportunity to make a real impact. This position is for an existing vacancy. Roofr is building the application foundation that will define how AI is integrated across our entire product — and we need someone to make sure it actually works. As our Senior AI Quality Engineer, you'll sit on the AI Platform team and own the eval frameworks, testing standards, and quality gates that every engineering team at Roofr depends on to ship AI with confidence. But this role extends well beyond the platform — you'll work horizontally across the entire testing organization, training teams, embedding best practices, and raising the bar on how Roofr tests everything it builds with AI. This is early, foundational work — you're setting the standard for the whole org, not just one team.

Requirements

5–8 years of software engineering or quality assurance experience
Hands-on experience building eval frameworks for LLM-powered features — you've thought seriously about how to measure output quality, consistency, and regression, and you've worked with tools like Promptfoo, DeepEval, Braintrust, or similar
Strong engineering fundamentals — you write real code, build real tooling, and aren't reliant on manual testing processes
Experience integrating automated quality checks into CI/CD pipelines
Familiarity with LLM APIs and agent frameworks (e.g. Anthropic Claude, OpenAI, or similar) and the specific quality challenges they introduce
Experience designing human review workflows to complement automated evaluation
Strong collaboration skills — you'll be working across many teams, and the standards you set only work if engineers actually adopt them
Comfort operating in an early-stage environment where the right approach isn't always obvious and you'll need to figure it out
Genuine ownership mentality — you care about whether AI at Roofr works well, not just whether the tests pass

Responsibilities

Define the testing standards and patterns for AI at Roofr — establishing how product teams validate AI behaviour when building on top of the application foundation
Build and own Roofr's LLM eval framework — selecting and extending the right tooling (e.g. Promptfoo, DeepEval, Braintrust) and designing the methodology that measures whether our AI integrations and agent outputs are performing correctly, consistently, and safely
Integrate quality gates into CI/CD pipelines so that regressions in AI behaviour are caught before they reach production
Design and implement human-in-the-loop review processes for AI outputs where automated evaluation isn't sufficient
Embedded on the AI Platform team — ensuring quality is designed into the integration architecture from day one, not bolted on after the fact
Work horizontally across the testing organization — coaching QA engineers and developers on AI eval patterns, embedding best practices into team workflows, and actively raising the quality bar across engineering
Stay close to the evolving AI quality landscape — new eval techniques, benchmarking approaches, and tooling like Ragas, Arize Phoenix, or LangSmith — and bring the best of it to Roofr

Benefits

1st week of employment is mandatory PTO! Start your journey with Roofr by decompressing and recharging - we will see you in week 2!
1 Friday off per month (we call those our laundry days!)
Company wide paid shutdown for the week between Christmas and New Years
Flexible time off
80% employer-paid benefits in the U.S. and 100% employer-paid premiums for Extended Healthcare and Dental in Canada
RRSP/401k match
Generous Parental Leave policy
We host an annual company retreat with great team building activities
Ample learning and development opportunities to continue growing your career
Home office setup stipend
Internet and phone allowance
Remote first culture
Weekly Friday paydays!