Engineering Team Lead AI Platform

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 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

What You’ll Bring to the Role:

• 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

Compensation Range: $170,000 - $190,000 CAD

Our compensation ranges are built using multiple market benchmarks and reflect both the scope of the role and current market data. While many hires fall within the beginning to midpoint of the band to allow for growth over time, we tailor offers based on each candidate’s experience, seniority, and demonstrated impact.

🏠 What we offer (US + Canada)

When you join our team, you’re not just accepting a job. You’re making a career move. Here’s how we’ll support you in doing some of the most impactful work of your career:

🏝️ Vacation/Paid Time Off:

• 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

🤝 Perks:

• 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!

🤖 AI Notice

At Roofr, we’re big fans of AI. It helps us write job descriptions that don’t put you to sleep, takes notes during interviews so we can actually listen, and even helps us track down awesome humans like you.

Feel free to use AI to prep, research, or get pumped up for your interview (we see you, ChatGPT power users 👀). But when it’s time to chat, we’d love to meet you, not your AI alter ego. Bring your real, unfiltered self, we promise we will too.

And don’t worry, a real, live human is behind every part of our process. Every application is reviewed by a real person, and you’ll always speak with real humans throughout the interview process. No bots, just good people ☺️

⚠️ Important Notice

We’ve been made aware of an individual impersonating Roofr using a fraudulent domain: roofrr.com (note the extra “r”). Our company takes the security and privacy of job applicants very seriously. We will never ask for payment, bank details, or personal financial information as part of the application process. All our legitimate job postings can be found on our official career site. Please be cautious of job offers that come from non-company email addresses, instant messaging platforms, or unsolicited calls.

To ensure your application is legitimate, please apply directly through our official careers page: https://roofr.com/careers.

If you receive any suspicious messages or have questions, reach out to us at talent@roofr.com.

Your safety and security are important to us — thank you for your vigilance!

Roofr is proud to be an equal opportunity employer. We are committed to equal employment opportunity in the workplace regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status.