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Added 3 mins ago
Controls Engineer
Actalent
Cambridge, ON
$40 to $60 CAD / hour
Contract
Evaluate components and systems, providing recommendations to the design team.
Added 3 mins ago
Health & Safety Supervisor
FCC Construcción
Toronto, ON
Full-time
…activities cover all areas of engineering and construction. It is a leader in the execution of transport infrastructure, as well as in residential and non-residential construction. FCC…
Added 3 mins ago
Specialiste De Controle De Projets/Project Controls Specialist
Actalent
Levis, QC · Saint-Lambert-de-Lévis, QC
$50 to $80 CAD / hour
Contract
Added 3 mins ago
Hse Specialist
Actalent
Vancouver, BC
$32 to $45 CAD / hour
Full-time
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Added 3 mins ago
Human Resources Business Partner
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Oakville, ON
$90,000 to $140,000 CAD / year
Full-time
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Added 3 mins ago
Senior Security Engineer
Actalent
Ottawa, ON
$60 to $110 CAD / hour
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Job Title: Expert Security Engineer Vulnerability Prime
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Security Software Engineer
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$60 to $80 CAD / hour
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We're looking for a Security Software Engineer to help build and secure the systems that establish trust across devices, manufacturing environments, and cloud services. This role is ideal…
Added 3 mins ago
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Actalent
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$60 to $80 CAD / hour
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Senior Security Engineer
Actalent
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$60 to $110 CAD / hour
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Added 4 mins ago
Carbody Structure Designer
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…suppliers, industrialization teams, and the project management team, contributing to the creation of innovative rail vehicles. You’ll also play a part in ensuring high-quality designs are…
Added 19 mins ago
Anti-Cheat Programmer (March of Giants)
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Montreal, QC
Full-time
Ubisoft is a global leader in gaming with teams across the world creating original and memorable gaming experiences, from Assassin’s Creed, Rainbow Six to Just Dance and more. We believe…
Added 19 mins ago
Development Lead - Application Development
Air Canada
Toronto, ON
Full-time
…your career take flight by joining our diverse and vibrant team at the leading edge of passenger…
Added 49 mins ago
Job ID #32265: Manager, IT Operations
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Hamilton, ON
Full-time
…from the downtown core, and so much more. Join our diverse team of talented and ambitious staff who embody our values of sensational service, courageous change, steadfast integrity,…
Added 49 mins ago
Senior Financial Analyst, Corporate Financial Reporting
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Toronto, ON
Full-time
Thank you so much for considering our company in your career search! Classic Fire + Life Safety is a leader in the fire protection and life safety industry because of our talented,…
Added 1 hour ago
Technician II – Vehicle Maintenance
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Toronto, ON · Scarborough, ON
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Light Equipment Operator - Winter
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Class 3 Service Driver
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Winter Crew Member / Lead
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AI Solution Principal
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Beutel Goodman is seeking a strategic and collaborative leader to join our team as VP, Enterprise Risk Management. This role is responsible for leading the firm's enterprise risk management…
Added 2 hours ago
Delivery Driver
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Martell Ventures

Technical Leader

Waterloo, ON, Canada

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

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 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.

Apply About employer

More about this job

Responsibilities

You will lead product engineering by setting technical direction, writing production code, and coordinating a high-performing team. Additionally, you will partner with business leadership to translate company priorities into a scalable technical roadmap while reporting progress to the board.

Requirements

Candidates must have 7+ years of experience building and operating production software with a proven track record in technical leadership. You should also possess strong expertise in AI-enabled development workflows, system architecture, and the ability to communicate complex technical decisions to non-technical stakeholders.

Skills

Technical leadership
Software architecture
AI-native development
Product engineering
Team management
CI/CD
System reliability
Security
Performance optimization
Incident response
Strategic planning
Stakeholder communication
Code review
Debugging
Roadmap development

Benefits

Equity compensation
Performance-based compensation

Visa sponsorship

Not detected in the job text

Keywords

AI-powered sales platform
B2B SaaS
Technical Leader
Product Engineering
Architecture
AI agents
CI/CD
Testing
Documentation
Monitoring
Incident response
Scalability
Security
Performance
Code review
Deployment
Operations
Technical roadmap
Business strategy
Stakeholder management
Early-stage environment
Automation
Engineering fundamentals
Production software
AI models

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