Technical Leader

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

Compensation: OTE $250K to $1M+ (salary, performance-based, and equity compensation)

Location: Waterloo, ON

About Winly

Winly is an AI-powered sales platform that helps teams turn digital conversations into qualified opportunities and booked calls. It is a Martell Ventures portfolio company with the ambition to build a category-defining product and a highly leveraged, AI-first operating model.

About Martell Group

The Martell Group exists to build people, brands, and ventures that create meaningful impact. Across our four companies, we combine audience, operators, and execution to launch scalable products and empower ambitious leaders in Media, B2B SaaS, and AI.

Founded by serial entrepreneur and investor Dan Martell (investor in Udemy, Intercom, and Unbounce), we're building a company that values leadership, growth, and simplicity, and we're looking for people who live those values too.

Our goal is to attract world-class talent and align people where their impact is greatest. When you apply to Martell Group, you'll automatically be considered for all open roles across our companies, not just the one you applied for.

About the Role

We'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 Do

1. 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 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.