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Serv Recruitment

Technical Leader

Waterloo, ON, Canada

Job type: Full-time
Apply by: Oct 29, 2026
Experience: 7+ years building and operating production software, including experience leading a small team, contractors, or a technical function.
Posting language: English
Posted: Sep 29, 2026

Apply About employer

Applications open in a new tab.

Original job description

Serv, a global executive recruitment partner, is hiring on behalf of our client Winly for a Technical Leader.

Join the Team:

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.

For more information, visit: https://www.danmartell.com/

Why you shouldn't work here: Radical Transparency from our CEO

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.

Position Responsibilities:

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.

This role includes:

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.

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.

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.

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.

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.

Qualifications:

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.

Our Ideal Teammate Is Someone Who:

Is proactive and accountable
Thinks strategically while remaining deeply hands-on
Communicates with clarity and confidence
Thrives in a fast-paced, early-stage environment
Operates with a high level of ownership and sound judgment
Is comfortable making pragmatic decisions as priorities evolve
Balances speed, quality, cost, and technical risk
Uses AI-first thinking to increase leverage and improve how work gets done
Creates clarity and accountability without adding unnecessary process
Cares deeply about building reliable products and delivering measurable business impact

Location: Waterloo, ON (In-Office)

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

Apply About employer

More about this job

Responsibilities

Own Winly’s product engineering direction, architecture, reliability, and technical roadmap while remaining hands-on with production code and coordinating a small team of engineers and contractors. Build an AI-first development workflow, partner with the Business Leader on product and business priorities, and report progress, risks, and investment needs to the board.

Requirements

Requires 7+ years of experience building and operating production software, including experience leading a small team, contractors, or a technical function. Candidates should have a strong hands-on engineering record, experience shipping AI-enabled features, sound product judgment, experience owning system reliability and operations, and clear communication skills.

Skills

Technical Leadership
Software Architecture
Hands-On Software Development
AI-Enabled Product Development
AI Agent Workflows
Team Leadership
Product Strategy
Roadmap Planning
Reliability Engineering
Security
Performance Optimization
CI/CD
Automated Testing
Incident Response
Stakeholder Communication
Board Reporting

Visa sponsorship

Not detected in the job text

Keywords

AI-First Engineering
AI Agents
AI Models
AI-Native Development Tools
Production Software
Software Architecture
Product Engineering
Technical Roadmap
Product Strategy
Automated Testing
CI/CD
Code Review
Documentation
Monitoring
Incident Response
Reliability
Security
Performance
Uptime
Deployment
Engineering Workflows
Development Velocity
Cycle Time
Release Frequency
Technical Risk
Early-Stage Environment
Board Reporting
B2B SaaS
Sales Platform
Digital Conversations

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