[Hiring] Engineering Team Lead, AI Platform @Roofr

Role Description

Roofr is at an inflection point with AI, and this role is at the center of it. As Engineering Team Lead of our AI Platform team, you'll own the application foundation that makes AI a native part of how Roofr's product works — establishing the integration architecture, agent patterns, and core abstractions that every product team will build on top of. This isn't a siloed role — you'll work horizontally across the entire engineering department, making you one of the most cross-cutting and influential contributors in the org. This is a rare opportunity to define how an entire product organization integrates with AI from the ground up. The architectural decisions you make here will be the ones every team follows for years.

What You'll Get to Do:

• Build and lead a team of platform engineers, setting technical direction, conducting code reviews, and mentoring engineers as the team grows
• Define and build the application-layer foundation for AI at Roofr — establishing the core integration patterns, agent architecture, and shared abstractions that product teams across the org will build on
• Own the integration architecture strategy — making the foundational decisions on how Roofr's product connects to AI services and third-party systems, and setting the standard for how the rest of engineering builds with AI
• Design and maintain our third-party integration layer, establishing scalable, reliable patterns for connecting Roofr to external services and APIs
• Build the data pipelines that power our AI features — structured data feeds, embeddings, retrieval infrastructure, and more
• Take strong ownership over platform reliability, performance, and developer experience — the teams building on top of you depend on it
• Partner with product and engineering leadership to shape the AI roadmap and help the broader organization understand what's possible
• Navigate a maturing codebase and help drive architectural consistency across domains with varying levels of maturity
• Establish standards and best practices for how Roofr builds with AI — from SDK design to observability and reliability
• Evaluate emerging models, frameworks, and tooling and make pragmatic, well-reasoned bets on adoption

Qualifications

• 7+ years of software development experience, with 3+ years in a technical leadership role
• Practical, hands-on experience building production AI systems — you've shipped agents, integrations, or AI-powered features at scale, not just experimented with APIs
• Deep familiarity with LLM APIs and agent frameworks (e.g. Anthropic Claude, OpenAI, LangChain, or similar)
• Experience building evaluation pipelines and quality benchmarks for LLM-powered systems
• Strong background in integration architecture — designing reliable, extensible connectors to third-party services
• Experience building data pipelines that feed AI systems, including familiarity with RAG, embeddings, and vector search patterns
• Backend engineering depth with a track record of building systems that scale — fullstack experience is a plus
• Experience with PHP/Laravel is an asset; what matters most is that you've built scalable backend platforms and can learn the stack
• Proven ability to take ownership — you think beyond your tickets, care about the long-term health of what you build, and hold a high bar for quality
• Comfort being a strong individual contributor while also growing and guiding a team
• Strong communication skills — you can articulate complex technical tradeoffs clearly to engineers and non-technical stakeholders alike
• Experience at an early-stage or high-growth company, and the ability to thrive with the pace and ambiguity that comes with it
• A genuine excitement for what AI makes possible — and the pragmatism to build it well

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
• 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!