Head of Technology

Workleap; Montreal (administrative region); Hybrid; CAD 170,000 - 210,000; Full time

Benefits offered by this job

Annual bonus

LTIP

Health insurance

Telemedicine

Wellness budget

Remote work

Office access in Montreal

In-person gatherings

Claude access

Job summary

Workleap is seeking a Head of Technology to lead the Shared Tech group of ~20 engineers in Montreal. You’ll drive end-to-end value, accelerate delivery, and increase autonomy across Product Ops, Data, and Security & Infrastructure.

This role shapes a fast, high-impact engineering culture aligned with AI-enabled development. You’ll partner with product leaders to balance speed, quality, and security while maintaining strong architectural integrity and team growth.

Qualifications

• 8+ years in engineering leadership within scaling SaaS.
• Experience transforming teams to ship value with autonomy.
• Hands-on technical credibility and ability to influence architecture decisions.

Responsibilities

• Lead Shared Tech group (~20 people) spanning Product Ops, Data, and Security & Infrastructure.
• Stabilize, clarify, and accelerate engineering delivery.
• Drive end-to-end value with AI-enabled automation across the lifecycle.
• Partner with product line heads to ensure delivery speed and accountability.

Skills

Engineering leadership

Transformation experience

Team velocity improvement

Stakeholder influence

AI-enabled development

Quality and reliability

Decision making

French language

Microsoft/.NET familiarity

Montreal-based

Travel willingness

Tools

Microsoft/.NET ecosystem

Job description

Company Description

Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart, we make simple products that actually matter to the people who use them. We have two product lines: The Workleap Agent, our agentic HR platform that helps managers become better leaders, and ShareGate, the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us to do exactly that. We're intentional about who joins us. If you're the kind of person who gets excited by a hard problem and wants to help shape what comes next, there's a place for you here.

Your role

Workleap's engineering organization is at an inflection point. We have two ambitious product lines, teams that ship, and a real window to change how we build. What's needed now is someone who can move engineering from a support function to a true velocity engine — more autonomous, more AI-enabled, and capable of delivering end-to-end value without the dependencies that slow everyone down. As Head of Technology, reporting directly to the CPTO & Co-Founder, you'll lead the Shared Tech group (~20 people), spanning Product Ops, Data, and Security & Infrastructure — the foundation on which both product lines run. Your mandate: stabilize, clarify, and accelerate.

Your impact:

• Increase engineering velocity and impact by enabling teams to ship end-to-end value with minimal dependencies;
• Improve delivery performance through stronger deployment frequency, shorter lead times, and sustained production reliability;
• Reduce organizational friction by increasing team autonomy, simplifying workflows, and clarifying ownership;
• Accelerate delivery cycles and reduce manual effort through AI and automation embedded across development workflows;
• Increase the leverage of product teams through scalable platform capabilities across Product Operations, Data, and Security & Infrastructure;
• Strengthen accountability by aligning teams around production outcomes, customer impact, and end-to-end ownership;
• Elevate organizational performance by building strong technical leadership and high-performing teams.

Your team

Over the next 6 to 12 months, your mandate is clear: transform engineering into a faster, more autonomous, and more reliable delivery engine. Concretely, that means enabling end-to-end delivery with fewer dependencies, embedding AI and automation across the full development lifecycle, strengthening engineering systems and platform foundations to durably increase impact per builder, and reinforcing ownership and accountability across teams.

The challenge is as much organizational as it is technical — building systems that scale while changing how teams collaborate and deliver value. You'll take charge of the Shared Tech group (~20 people), where we build the standards, platforms, and enabling infrastructure that serve both product lines.

The team spans three pillars: Product Ops (builder tooling, AI SDLC, observability, analytics, billing), Data (single trusted AI-ready analytics backbone, governance, shared data science capability, AI quality foundations), and Security & Infrastructure (security architecture, compliance, incident response, infrastructure operations). You'll work in partnership with the heads of each product line — they own the product outcomes, your mission is to make delivery dramatically faster.

What you'll bring

• +8 years of experience in engineering leadership within a scaling or large-scale SaaS environment;
• Hands-on experience in transformation contexts, with a focus on improving team velocity, efficiency, and overall impact;
• Strong technical credibility with a hands-on mindset: ability to go deep, understand systems, and contribute to technical decisions;
• Experience managing and developing leaders within engineering organizations of approximately 20-30 people;
• Strong ability to influence in matrix environments and quickly build credibility with senior stakeholders;
• Proven ability to improve execution while maintaining high standards of quality, reliability, and judgment;
• Sound judgment to navigate trade-offs between speed, quality, security, and innovation;
• Strong interest in modern engineering practices, particularly in AI-influenced development environments;
• Experience with the Microsoft / .NET ecosystem, or strong ability to ramp up quickly;
• Good understanding of French (written and spoken) required;
• Based in Montreal or able to travel regularly.

What the job comes with

• Annual bonus program.
• LTIP program, share in Workleap's long-term growth.
• RRSP + Family health insurance + telemedicine + annual wellness budget.
• Flexible vacation policy.
• Remote work, with access to our Montreal office.
• In-person gathering twice a year.
• Claude access, for everyone.

What drives us

At Workleap, we build software that sits at the center of how people experience work, every day, at every level.

We move fast. Priorities shift, decisions get made with the information we have, and we iterate. If you thrive on intensity and ambiguity doesn't slow you down, you'll feel right at home.
We're builders. We do what it takes to move forward. AI is part of our toolkit. We use it to go faster and decide smarter, not to replace judgment.

If you want real impact and a place where your decisions matter, this is it.

How we hire

Transparency is how we hire — for you as much as for us.

Here's how it works: a first call with a recruiter, then a virtual interview with the hiring manager. You'll then complete a take-home case study, followed by a meet with future colleagues to discuss it together. Depending on the role, the process may vary slightly — your recruiter will walk you through it on your first call.

We use AI to support certain steps of the process, but every hiring decision remains human.

We can't wait to meet you.

#LI-Remote