Remote Head of Technology, Transformation Full-Stack Builder

Company Description

Workleap is a Montreal-based tech company on a mission to make work simpler.

Since 2006, we’ve been building game-changing products that tackle HR and IT’s biggest challenges.

Workleap operates two distinct product lines:

• The Workleap Platform , an AI-powered HR solution designed to drive team performance and boost employee engagement.


• ShareGate , the leading Microsoft 365 migration and governance solution, trusted by IT professionals worldwide for its unmatched simplicity.

Today, more than 20,000 companies rely on Workleap products to grow, lead, and operate with confidence.

We’re builders at heart, with a clear purpose: to craft the simplest products that deliver exceptional value for our customers. Period.

Job Description

So, what will your new role look like?

As a Head of Technology, your mission will be to advance the organization's execution capacity by influencing, aligning, and evolving key teams. The role is centered on three shared functions — Product Ops, Data, and Security Operations — with a clear transformation mandate: stabilize certain teams, support a new dynamic around AI, clarify priorities, and increase velocity without compromising quality. This position requires someone capable of making an impact in a matrix structure, leading through technical credibility and influence, and concretely contributing to the engineering vision.

Responsibilities:

• Stabilize the teams under your responsibility and create conditions for effective collaboration in a context of organizational evolution.


• Define and advance an engineering vision that improves execution speed at the organizational scale.


• Lead the shared functions of Product Ops, Data, and Security Operations to better support product teams.


• Establish clear benchmarks for performance and velocity, then guide teams toward measurable gains over time.


• Accelerate delivery by reducing friction, dependencies, and obstacles between teams.


• Make informed decisions on trade-offs between velocity, quality, and security based on business needs.


• Collaborate closely with product leaders and other key partners to maximize organizational impact.


• Inspire and mentor technical leaders by providing clarity, alignment, and direction in gray areas.


• Contribute concretely to technical initiatives to establish your credibility and lead by example.

What does your future team look like?    

You'll lead the Shared Tech group (~20 people): where we build the standards, the platforms, and the enabling infrastructure that serve both product lines (ShareGate and Workleap). You'll partner with the heads of each product line who own the product outcomes, and your mission is to make delivery dramatically faster.

The three pillars of your scope:

• Product Operations: Builder tooling, AI SDLC, observability, analytics, billing and subscription. Turn product activity into decisions and improve developer velocity.


• Data: Single trusted, AI-ready analytics backbone. Shared data models, governance, data science as a shared capability, AI quality foundations.


• Security & Infrastructure: Enterprise-grade trust without killing speed. Security architecture, compliance, incident response, infrastructure operations.

Qualifications 

• Significant experience (at least 3–5 years) in an engineering leadership role within a growing or large-scale SaaS technology environment;


• Demonstrated ability to influence without relying solely on hierarchical authority, particularly in matrix structures;


• Strong technical credibility and willingness to be hands-on: ability to go deep, understand code, and contribute concretely;


• Experience managing leaders, including contexts where 3 directors may report to the position;


• Relevant experience managing or coordinating organizations of approximately 20 people;


• Ability to lead organizational transformation mandates with high expectations for impact;


• Experience improving execution velocity while maintaining a high level of quality;


• Good judgment to navigate trade-offs between security, quality, innovation, and speed;


• Strong interest in new ways of developing software in an AI-influenced context;


• Ability to quickly establish credibility with very senior profiles and to challenge strong opinions constructively;


• Experience in a Microsoft / .NET environment is an asset; otherwise, a strong interest in quickly learning this ecosystem is important;


• Presence in Montreal preferred, and ability to travel to the office occasionally.

 

Who we are

We’re a team of curious minds and bold builders, brought together by a shared drive to make work simpler - and better - for everyone. Challenges fuel our creativity, fast-paced environments keep us sharp, and pushing boundaries is just part of how we operate. We believe the best ideas come from experimentation, rapid learning, and even the occasional discomfort - that’s where growth happens.

Since 2006, we’ve been rethinking the way teams work, blending creativity and tech to solve real problems in IT and HR. We move quickly, we learn constantly, and we always keep our customers at the center of what we do. If you're a proactive thinker who takes ownership, loves to collaborate, and isn’t afraid to leap into the unknown - you’ll fit right in.

Additional Information

At Workleap, we build together, we trust each other, and we support each other in success or failure. You will be able to express yourself, evolve and develop your creativity in an environment that will adapt to your daily life and your needs.

We strive to create a healthy and inclusive work environment. This is everyone’s business. 

Our Candidate Experience Flow at Workleap: 
Phone Screen - Virtual Interview using Microsoft Teams - Work Sample - Job Offer

As a tech-forward company, we leverage AI tools to enhance our recruitment process, while ensuring all hiring decisions remain human-led.

We are looking forward to getting to know you! 

By applying to this job, you are confirming that you have read and agree to the terms of our .

#LI-Remote