AI-First Tech Leader — Hands-on & Team Builder

Dan Martell; Southwestern Ontario; Hybrid; CAD 250,000 - 1,000,000; Full time

Job summary

Winly, an AI-powered sales platform, seeks an AI-first Technical Leader to own product engineering. You'll code daily while guiding a small team of engineers and contractors, moving fluidly between architecture, product decisions, and hands-on development.

You will translate business priorities into a focused technical roadmap, partner with the Business Leader, and report progress, risks, and key decisions to the Martell Ventures board.

Qualifications

• 7+ years building and operating production software with leadership experience.
• Hands-on builder capable of owning systems from architecture to deployment.
• Experience shipping AI-enabled features and using modern AI models and tools.
• Strong product judgment linking technical decisions to customer outcomes.
• Experience ensuring uptime, security, performance, and cost control.
• Clear communication with technical and non-technical stakeholders, including executives.

Responsibilities

• Define technical direction and pragmatic architecture aligned with company strategy.
• Stay hands-on: write production code, review PRs, debug issues, ship improvements.
• Own reliability, security, performance, and customer experience quality.
• Build an AI-first engineering organization with testing, CI/CD, monitoring, and docs.
• Lead a small team of engineers and contractors toward clear outcomes and standards.
• Translate customer insight into focused product and engineering roadmaps.
• Report roadmap progress, performance, risks, and investments to the board.

Skills

Hands-on software engineering

Technical leadership

AI features experience

Product judgment

System reliability

Clear communication

Tools

AI development tools

CI/CD

Job description

Winly, an AI-powered sales platform, seeks an AI-first Technical Leader to own product engineering. You'll code daily while guiding a small team of engineers and contractors, moving fluidly between architecture, product decisions, and hands-on development.

You will translate business priorities into a focused technical roadmap, partner with the Business Leader, and report progress, risks, and key decisions to the Martell Ventures board.