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Added 40 mins ago
Senior Staff Cloud Security Engineer | Operational Technology | Office of CISO
ServiceNow
AB · Alberta, CANADA
Full-time
It all started when engineer Fred Luddy wrote code that automated a tedious task for his coworker, Phyllis. She cried tears of joy. That moment inspired Fred to build a company that could…
Added 3 hours ago
Data Engineering, Cloud Migration & Platforms Engineer
General Motors
Markham, ON
Full-time
Lead or support incident response, service recovery, root cause analysis, and post-incident reviews for data-platform and pipeline issues.
Added 6 hours ago
Senior Embedded Software Designer
Kepler Communications Inc.
Toronto, ON
Full-time
…we’re committed to creating an environment where you can grow, lead, and make a global…
Added 6 hours ago
Junior Resource Strategy Analyst
AtkinsRéalis
Mississauga, ON
Full-time
Assist lead to develop and maintain short-term and long-term resource forecasts based on project portfolios, business pipelines, and operational requirements.
Added 7 hours ago
Lead AI Engineer
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Toronto, ON · Waterloo, ON · Sun Life Toronto Atria
Full-time
Corporate IT is seeking an experienced Lead AI Engineer to design, develop, deploy, and support enterprise-grade Artificial Intelligence, Machine Learning, and Generative AI solutions on…
Added 8 hours ago
Senior Application Security Engineer
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The Senior Application Security Engineer is a senior technical role responsible for advancing security across the software development lifecycle (SDLC). Working closely with application…
Added 8 hours ago
Senior Application Security Engineer
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Full-time
The Senior Application Security Engineer is a senior technical role responsible for advancing security across the software development lifecycle (SDLC). Working closely with application…
Added 9 hours ago
Senior Technical Program Manager
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CNN is hiring a Senior Technical Program Manager to lead high-impact programs that span product, technology, design, and product operations. This is a deeply technical senior…
Added 9 hours ago
Sales Development Representative
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…driving analytics for greater efficiency, your ideas will help engineer solutions for stronger communities and a sustainable…
Added 9 hours ago
Principal Geotechnical Engineer
WSP in Canada
Saskatoon, SK
Full-time
…engineering presence across Saskatchewan. As a Principal Geotechnical Engineer , you'll leverage your established industry relationships, reputation, and expertise to develop new client…
Added 10 hours ago
Development Team Lead
UniSysTech Consulting
Toronto, ON · Greater Toronto Area, Canada
Other
As a technical lead, you will bridge the gap between architecture, product strategy, and engineering execution - mentoring talent, driving engineering best practices, and ensuring robust…
Added 10 hours ago
Digital Architect – Data - GOAPRDJP00000987
S M Software Solutions Inc
AB · Edmonton, AB
Full-time
…will provide architectural expertise and strategic guidance, lead solution architecture, support cross-functional agile product teams, and help deliver user-centric digital services aligned…
Added 10 hours ago
Principal Geotechnical Engineer
WSP in Canada
Regina, SK
Full-time
…engineering presence across Saskatchewan. As a Principal Geotechnical Engineer , you'll leverage your established industry relationships, reputation, and expertise to develop new client…
Added 10 hours ago
Digital Architect – Data - GOAPRDJP00000987
S M Software Solutions Inc
AB · Edmonton, AB
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…will provide architectural expertise and strategic guidance, lead solution architecture, support cross-functional agile product teams, and help deliver user-centric digital services aligned…
Added 10 hours ago
Digital Architect – Data - GOAPRDJP00000987
S M Software Solutions Inc
AB · Edmonton, AB
Full-time
…will provide architectural expertise and strategic guidance, lead solution architecture, support cross-functional agile product teams, and help deliver user-centric digital services aligned…
Added 10 hours ago
Application Development - Senior IAM Systems Engineer - Advanced
Raise
Toronto, ON
Full-time
We at Raise are hiring a Application Development - Senior IAM Systems Engineer - Advanced for one of our top clients. After establishing themselves as an industry leader, they’re now…
Added 11 hours ago
Senior Data Platform Engineer - Zonda - Toronto, Ontario
CoStar
Toronto, ON
$140,000 to $170,000 CAD / year
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We are looking for a Senior Data Platform Engineer to design, automate, and operate the shared capabilities that underpin our enterprise data platform.
Added 11 hours ago
Electrical Engineer - Intermediate - Mining & Metals
Fluor
Vancouver, BC
Full-time
…value and technical competence. This position supports the Area Lead or Lead on assigned projects or evaluates, selects, and applies standard engineering techniques to a medium set of…
Added 11 hours ago
Intermediate Civil Design Engineer
Fluor
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…value and technical competence. This position serves as an Area Lead on assigned projects or performs moderately complex engineering assignments, evaluates, selects, and applies standard…
Added 11 hours ago
Principal Design Engineer/ Mechanical Lead - for Mining & Metal projects
Fluor
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At least 5 years of experience serving as Lead Engineer on mining and metals projects
Added 11 hours ago
Principal Cloud & AI Apps Solution Engineer
Microsoft
Toronto, ON
Full-time
…& Apps and a broad leadership mandate across the Microsoft platform. You will lead strategic technical engagements, orchestrate expertise across Business Applications, Security, Cloud & AI…
Added 12 hours ago
Staff Software Engineer, Core Applications
Solink
Remote, Canada
$138,445 to $173,056 USD / year
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Reports To: Xiaokun Xu, Application Team Lead
Added 12 hours ago
Principal Research Scientist
ServiceNow
Montreal, QC
Full-time
It all started when engineer Fred Luddy wrote code that automated a tedious task for his coworker, Phyllis. She cried tears of joy. That moment inspired Fred to build a company that could…
Added 12 hours ago
Site Reliability Engineer II (AI Platform)
OpenTable
Toronto, ON
As a Site Reliability Engineer II on the Serving Platforms team within Infrastructure Engineering, you will design, automate, and manage the core container stack and infrastructure powering…
Added 13 hours ago
Kubernetes Reliability Engineer
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The CaaS IT Infrastructure Engineer is a highly skilled expert responsible for solving complex business problems using advanced cloud native technologies. The engineer will build and…

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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