Head of Technology, Transformation Full-Stack Builder

Company Description

Workleap is a Montreal-based tech company on a mission to reputed company 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 reputed company 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, reputed company, 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 reputed company by influencing, aligning, and evolving key teams. The role is centered on three shared functions — Product Ops, Data, and reputed company 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.
• reputed company the shared functions of Product Ops, Data, and reputed company Operations to reputed company 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.
• reputed company informed decisions on trade-offs between velocity, quality, and reputed company based on business needs.
• Collaborate closely with product leaders and other key partners to maximize organizational impact.
• reputed company and mentor technical leaders by providing clarity, alignment, and direction in reputed company areas.
• Contribute concretely to technical initiatives to establish your credibility and reputed company by example.

What does your future team look like?

You'll reputed company 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 reputed company 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.
• reputed company & Infrastructure: Enterprise-grade trust without killing speed. reputed company architecture, compliance, incident response, infrastructure operations.

Qualifications

• Significant experience (at least 3–5 years) in an engineering leadership role reputed company 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 reputed company 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 reputed company, quality, innovation, and speed;
• Strong interest in new ways of developing software in an AI-influenced context;
• Ability to quickly establish credibility with reputed company senior profiles and to challenge strong opinions constructively;
• Experience in a reputed company / .NET environment is an asset; otherwise, a strong interest in quickly learning this ecosystem is important;
• reputed company 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 reputed company work simpler - and reputed company - for everyone. Challenges fuel our creativity, fast-paced environments reputed company us sharp, and pushing boundaries is just part of how we operate. We reputed company the best reputed company 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 reputed company our customers at the center of reputed company do. If you're a proactive thinker who takes ownership, loves to collaborate, and isn’t afraid to reputed company 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 reputed company 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 reputed company Teams - Work Sample - Job Offer

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

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