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Added 11 mins ago
Principal Cloud & AI Apps Solution Engineer
Microsoft
Toronto, ON
Full-time
…engagements, bringing deep expertise in application architecture, agent development, application modernization, and cloud-native…
Added 11 mins ago
Stagiaire développeur IA & automatisation
Ericsson
Montreal, QC
Full-time
Évaluez quand utiliser l'automatisation traditionnelle, un service logiciel, un agent ou une combinaison d'approches.
Added 1 hour ago
Principal Research Scientist
ServiceNow
Montreal, QC
Full-time
Added 1 hour ago
Loss Prevention Store Security Agent
TJX Canada – Winners, Marshalls, HomeSense
Surrey, BC
$37,590 to $52,626 CAD / year
Full-time
We're seeking a Loss Prevention Store Security Agent to help create a safe, secure, and welcoming environment in our stores. In this impactful role, you’ll be instrumental in theft…
Added 2 hours ago
Senior Data Platform Developer - AI Platform
Geotab
Oakville, ON
Full-time
…and deliver results! Geotab is seeking a Senior Data Platform Developer who will be building the Geotab internal machine learning and generative AI platform. This role allows all Geotab…
Added 2 hours ago
Senior Data Platform Developer - AI Platform
Geotab
Toronto, ON
Full-time
…and deliver results! Geotab is seeking a Senior Data Platform Developer who will be building the Geotab internal machine learning and generative AI platform. This role allows all Geotab…
Added 2 hours ago
Senior Data Platform Developer - AI Platform
Geotab
Waterloo, ON
Full-time
…and deliver results! Geotab is seeking a Senior Data Platform Developer who will be building the Geotab internal machine learning and generative AI platform. This role allows all Geotab…
Added 2 hours ago
Sr Associate Machine Learning Engineer
Workday
Vancouver, BC · Canada, BC, Vancouver
Full-time
…that will revolutionize our customers' workday? Join the AI Agent Engineering team, where we're pioneering cutting-edge HR & Finance AI Agents that deeply integrate within the Workday…
Added 2 hours ago
Principal Engineer (API Platform)
Xero
Remote, Canada
Full-time · Remote
…and steward will serve as the trusted foundation for AI- and agent-driven automation across Xero’s accounting workflows; meaning you will be thinking not just about today’s developer…
Added 2 hours ago
Senior Software Engineer, AI Enablement
Xero
Vancouver, BC
Full-time
Developing guidance and best practice for authoring agent skills, including agents for remediation tasks
Added 3 hours ago
Manager, Internal Audit, Regulatory Compliance and Risk Management (Bilingual FR/EN)
PwC
Montreal, QC
Full-time
Added 3 hours ago
Data and Product Analyst (Contract)
PwC
Toronto, ON
Full-time
Added 3 hours ago
Senior ServiceNow Developer
Symbiotic Digital
ON · Cornwall East, Ontario
Contract
The Sr. Software Developer will design, implement, and
Added 3 hours ago
Senior Lifecycle Marketing Manager
VelocityEHS
Canada
Full-time
Lead the use of Marketo and 6sense email solutions, including the AI Email Agent (AIE), overseeing nurture programs, segmentation, personalization, automation, and standards for…
Added 3 hours ago
Senior Software Developer, Build Platform
Wealthsimple Technologies
Remote, Canada
$152,000 to $189,000 CAD / year
Full-time · Remote
As a Developer on our team, you won't just be building tools; you'll be shaping the entire developer journey at Wealthsimple. From their first day onboarding to their thousandth code…
Added 3 hours ago
Group Lead, AI Governance
Kraft Heinz
Toronto, ON
Full-time
Experience with cloud and identity controls, CI/CD, model/agent lifecycle management, observability, incident management, and production support (preferably Microsoft Azure)
Added 3 hours ago
Lead Analytics Solutions Developer
Enercare Inc.
Markham, ON
Full-time
The Lead Analytics Solutions Developer is the senior technical authority for how Enercare’s business data is modelled, defined and delivered for analysis. You will design the data…
Added 3 hours ago
Senior Data Integration Engineer
Connor, Clark & Lunn Financial Group Ltd.
Vancouver, BC
Enable real-time and event-driven data flows to support autonomous agent decision-making.
Added 3 hours ago
Senior Data Integration Engineer
Connor, Clark & Lunn Financial Group Ltd.
Toronto, ON
Enable real-time and event-driven data flows to support autonomous agent decision-making.
Added 4 hours ago
AI Solutions Engineer
Connor, Clark & Lunn Financial Group Ltd.
Vancouver, BC
Experience with agent frameworks (e.g., LangChain, LlamaIndex or equivalents), including tool use, orchestration, and multi-step flows
Added 4 hours ago
AI Solutions Engineer
Connor, Clark & Lunn Financial Group Ltd.
Toronto, ON
Experience with agent frameworks (e.g., LangChain, LlamaIndex or equivalents), including tool use, orchestration, and multi-step flows
Added 4 hours ago
Product Engineer
Insight Global
Toronto, ON
$150,000 to $180,000 CAD / year
Full-time
…including orchestration pipelines, evaluations, and LLM-based agent models - Experience working with agentic AI or orchestration frameworks such as LangChain, LangGraph, Mastra, or similar…
Added 4 hours ago
Allstate Sales Agent
Allstate Canada
Ottawa, ON
Full-time
As an Allstate Sales Agent, you’ll grow your own book of business, build strong relationships in your community, and help people protect what matters most. This is a hybrid role, where…
Added 4 hours ago
Staff Software Engineer (Fullstack, BE-leaning)
Apostra
ON · United Counties of Stormont, ON
Contract
In this role, you’ll be a technical leader responsible for the APIs, protocols, and agent interfaces that power our agentic advertising platform. You’ll design systems where AI agents are…
Added 4 hours ago
Loss Prevention Store Security Agent
The TJX Companies, Inc.
Mississauga, ON · Surrey, BC · CAN Home Office Mississauga ON
$37,590 to $52,626 CAD / year
Full-time
We're seeking a Loss Prevention Store Security Agent to help create a safe, secure, and welcoming environment in our stores. In this impactful role, you’ll be instrumental in theft…

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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