Compensation: OTE $250K to $1M+ (salary, performance-based, and equity compensation)
Location: Waterloo, ON
About the RoleWe're looking for an AI-first Technical Leader to own product engineering at Winly. You'll write code every day while coordinating a small, high-performing team of engineers and contractors.
This is a player-coach role for someone who can move fluidly between architecture, product decisions, hands-on development, and team leadership. You'll partner closely with the Business Leader to translate company priorities into a focused technical roadmap, and you'll report progress, risks, and key decisions to the Martell Ventures board.
Your mandate is to build a reliable, scalable product; use AI to increase the speed and quality of development; and create a technical organization that can grow with the business.
What You'll Do1. Own the product and technology- Set the technical direction and make pragmatic architecture decisions that support the company's strategy.
- Stay deeply hands-on: write production code, review pull requests, debug critical issues, and ship meaningful product improvements.
- Own reliability, security, performance, and the quality of the customer experience.
2. Build an AI-first engineering organization- Use AI-native development tools and workflows to help a small team produce exceptional output.
- Establish strong engineering fundamentals, including testing, CI/CD, code review, documentation, monitoring, and incident response.
- Continuously improve how the team plans, builds, ships, and learns.
3. Lead a small, high-performing team- Coordinate engineers and contractors around clear outcomes, priorities, and standards.
- Create the context, feedback loops, and accountability needed for people to do their best work.
- Identify when to hire, contract, automate, or simplify as the company grows.
4. Partner with the Business Leader- Turn customer insight and business priorities into a focused product and engineering roadmap.
- Balance speed, quality, cost, and technical risk when making decisions.
- Bring technical judgment into company planning, resource allocation, and product strategy.
5. Communicate with the board- Report to the Martell Ventures board on roadmap progress, product performance, technical health, risks, and investment needs.
- Communicate complex technical decisions in clear business terms.
- Surface issues early and bring thoughtful recommendations, not just problems.
What You Bring- 7+ years building and operating production software, including experience leading a small team, contractors, or a technical function.
- A strong track record as a hands-on builder who can own systems from architecture through deployment and operations.
- Experience shipping AI-enabled product features and working with modern AI models, tools, and development workflows.
- Strong product judgment and the ability to connect technical decisions to customer and business outcomes.
- Experience building reliable systems and owning uptime, security, performance, cost, and incident response.
- The ability to create clarity, set standards, and keep a small team moving quickly without adding unnecessary process.
- Clear communication skills with both technical and non-technical stakeholders, including executives and boards.
- High ownership, sound judgment, and comfort operating in an early-stage environment where priorities evolve quickly.
Success Looks Like (First 120 Days)- Agentic pipeline. Winly's development workflow has been rebuilt around AI agents-from planning and implementation through testing, review, documentation, and deployment.
- Team adoption. Every engineer and contractor is effectively using the pipeline, with clear standards, shared workflows, and documented best practices.
- Quality guardrails. Automated tests, CI/CD, code review, monitoring, and human approval points allow agents to move quickly without compromising reliability or security.
- Measurable leverage. Development velocity, cycle time, release frequency, and quality are measured, with clear evidence that the team is shipping faster and more consistently.
- Hands-on leadership. You are actively contributing code while continuously improving the systems that multiply the output of the entire team.
- Scalable foundation. The Business Leader and Martell Ventures board have a clear view of the pipeline's performance, risks, and roadmap for further automation.
