Job Description

So, what will your new role look like?

As Head of Technology, your mission is to evolve Workleap’s engineering organization toward a more autonomous, efficient, and AI-enabled model. You will lead the Shared Tech group and help accelerate the organization’s execution by aligning and evolving key teams. The role spans three core functions, Product Ops, Data, and Security & Infrastructure, with a clear mandate: stabilize, clarify priorities, and increase velocity without compromising quality. You will shape the systems, platforms, and practices that enable product teams to deliver faster, with greater autonomy and impact, by leveraging AI and automation.

Responsibilities:

• 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.

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 HR). 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.

Your role will be to evolve this group from a support function into a true engine of engineering velocity and impact.

What are the next challenges awaiting your team?

Your mandate is clear: transform engineering into a builder organization that can deliver faster without compromising quality or trust. In the next phase, the team will need to:

• Enable more autonomous, end-to-end product delivery with fewer dependencies and handoffs;
• Embed AI and automation throughout the development lifecycle to reduce manual work and accelerate execution;
• Strengthen the engineering systems and platform foundations that increase impact per builder over time;
• Replace manual processes with scalable, automated platform capabilities;
• Reinforce ownership and accountability across teams.

The challenge is both technical and organizational: building systems that scale while changing how teams collaborate, operate, and deliver value. Success means creating an engineering organization that operates as a high-leverage system, where small teams can deliver outsized customer impact at market speed.

Qualifications 

• +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.

Job Description 

So, what will your new role look like?

As Director, Security & Infrastructure, your role is to create the conditions for product and engineering teams to move faster with confidence. You will lead the infrastructure, security operations, and governance, risk, and compliance functions across Workleap and ShareGate, ensuring our environment remains reliable, scalable, and secure as the organization evolves. You will play a key role in supporting Workleap’s shift toward a Full-Stack Builder model, where small teams own the full journey from insight to production. This means building a platform and security foundation that reduces friction, strengthens trust, and helps teams ship quickly without compromising reliability, security, or compliance.

Responsibilities:

• Improve platform reliability and scalability so product teams can ship with confidence across Workleap and ShareGate;
• Reduce security and compliance risk through guardrails embedded directly into delivery workflows;
• Increase engineering autonomy by reducing dependency on centralized infrastructure support;
• Increase system resilience and minimize service disruption through stronger observability, incident response, and proactive capacity planning;
• Elevate team impact and organizational leverage by building a high-performing infrastructure and security function;
• Improve executive decision-making with clear, business-relevant visibility into security, compliance, and risk posture.

What does your future team look like?   

You will lead a platform-focused team spanning infrastructure, security operations, and GRC, supporting both Workleap and ShareGate. This team is evolving from a traditional support function into a platform enablement team, one that helps product teams move faster by providing reliable, secure, and easy-to-use foundations. Your role is to position this team as a force multiplier for engineering: reducing friction, increasing autonomy, and making security and infrastructure feel invisible to builder teams.

What are the next challenges awaiting your team?   

Your mandate is clear: transform infrastructure and security into silent foundations, robust in the shadows, transparent in everyday use, so that product delivery is smooth and the entire company stands on solid ground.

In the next phase, the team must:

• Enable true self-service so teams can build, deploy, and scale independently;
• Embed security directly into delivery workflows, eliminating manual gates;
• Strengthen platform reliability to support faster and more frequent releases;
• Shift governance from static control to continuous, automated assurance.

Beyond the systems, the real challenge is cultural: turning infrastructure and security into enablers of speed, not constraints. Success means product teams can ship faster with confidence and never have to slow down for infrastructure or security.

Qualifications

• 8+ years of experience across infrastructure and security leadership in technology organizations;
• Experience leading technical teams through transformation in fast-paced, evolving organizations;
• Strong expertise in cloud-native environments such as Azure or GCP;
• Hands-on experience with Kubernetes, infrastructure as code, and platform automation;
• Deep understanding of security frameworks, such as SOC 2, NIST CSF, ISO 27001, and CIS Controls;
• Proven ability to build secure, scalable, high-availability environments for SaaS products;
• Strong ability to communicate risk, priorities, and tradeoffs to executive and board-level stakeholders;
• CISSP, CISM, or equivalent credentials are considered an asset;
• Based in Montreal, or able to travel there a few times per quarter.

Job Description

So, what will your new role look like?

You are a hands-on engineering leader who builds great teams and ships great software. As Software Development Manager, you will build a new team from the ground up focused on modernizing ShareGate's architecture, setting the technical direction, staying close to the code, and earning the trust of your engineers.

This is not a purely people-management role. We expect you to lead from the front. 

Responsibilities:

• Build and shape a new team from the ground up, hiring, onboarding, and developing engineers who will own modernization work.
• Define and drive the technical direction for re-architecting and modernizing ShareGate's platform.
• Oversee the full software development lifecycle, from planning and execution to hands-on contributions in code, design, and quality.
• Drive engineering excellence across testing, security, observability, reliability, and performance, while optimizing delivery flow through CI/CD, automation, and tooling standards.
• Set clear expectations, manage technical debt pragmatically, and communicate trade-offs transparently with stakeholders.
• Coach and develop team members through technical challenges, 1:1s, performance reviews, and a culture of continuous learning and knowledge sharing.
• Partner closely with Product and Design to frame, scope, and deliver high-value, pragmatic solutions while anticipating risks.
• Play an active role in departmental strategic planning and contribute to key cross-team initiatives.

What does your future team look like? 

You will be building this team from scratch, which means you will have a direct hand in shaping its culture, technical standards, and ways of working from day one. The team's mandate is modernization, tackling the architectural work that sets ShareGate up for the next chapter of its growth. You will also be part of a broader engineering leadership group, collaborating on shared challenges and departmental goals.

Qualifications  

• 3+ years as a Software Development Manager, with a strong background as a software developer.
• Bachelor's degree in computer science or a related field, or equivalent experience.
• A background in leadership or management training is a plus.
• Proven experience leading modernization efforts, including legacy migration, re-architecture, or meaningful technical debt reduction at scale.
• Deep engineering fundamentals: able to set standards, review work credibly, and raise the bar across a team.
• Experience building teams, not just managing them, hiring, onboarding, and developing engineers from the ground up.
• A track record of developing engineers, influencing peers and directors, and collaborating effectively with Product and Design.
• Comfortable with Agile, whether Scrum, Kanban, or Lean, and pragmatic about how you apply it.

Salary range: $145K–$185K CAD.
This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate’s region to align with local market conditions.

Job Description

So, what will your new role look like?

We’re hiring a Staff Developer to lead the technical delivery of ShareGate’s most ambitious new feature, Backup, one of our customers' top requests. This marks a first for ShareGate in the migration space.

In this hands-on technical leadership role, you’ll own the architecture, define the long-term technical vision, and help build the team that will bring this highly requested capability to life.

Responsibilities:

• Lead the technical design, architecture, and delivery of the Backup feature, ensuring scalability, security, and long-term maintainability.
• Design and develop a new backup system that is reliable, automated, and easy to use, capable of meeting operational needs and recovery requirements.
• Define and champion a spec-driven development workflow, where features are designed upfront through detailed technical specifications before any code is written, enabling agentic AI-assisted development, faster reviews, and higher quality delivery.
• Collaborate with Product, Design, and directly with customers to validate our solutions, and align our technical direction to our product goals.
• Mentor developers, grow the team, and influence technical decisions across ShareGate’s engineering organization.
• Act as a visible technical leader, advocating for scalable design decisions, driving technical discussions, and influencing ShareGate’s broader engineering practices.

A typical week?   

You will spend your week advancing high-impact technical work: writing detailed specifications that serve as a contract between intent and implementation, leveraging agentic AI development tools to accelerate delivery, reviewing code and designs, facilitating design discussions, writing code, and solving complex Backup challenges, all in close collaboration with Product and Design. With a light meeting load and mostly async collaboration, you will have the space to prioritize deep work and problem solving.

In parallel, you’ll be shaping the long-term team in partnership with your Software Development Manager by participating in hiring, onboarding, and mentoring as the team grows.

What does your future team look like?   

You’ll be the first developer on this new team, taking full technical leadership from the start.

In the early stages, you’ll be supported by a Principal Developer as well as a small development team to define the technical foundation, architectural direction, and key delivery frameworks. With a dedicated Product Manager, Product Designer, and Manager already in place, you’ll have a unique opportunity to help select and shape the engineering team around you.

What are the next challenges awaiting your team?   

Your team’s first challenge is to deliver a secure, production-ready MVP to select customers. You’ll then iterate rapidly toward general availability while scaling the team to support the long-term growth of a feature area that'll play a progressively larger role in ShareGate's broader strategy.

All of this on which technical stack?  

You’ll be working within a mature .NET (C#) codebase supported by established tooling, CI/CD pipelines, and strong engineering standards.

Qualifications

• 10+ years of software development experience, with a significant portion in technical leadership roles.
• Advanced proficiency in C# and the .NET ecosystem, with familiarity with CI/CD pipelines, React, and ideally hybrid or desktop application environments.
• Hands-on experience with agentic development tools (Claude Code, Cursor, Copilot Agents, or equivalent) and comfort actively integrating them into your daily workflow.
• Proven technical leadership in large-scale enterprise system development, from design to delivery, with a sharp sense of user experience and empathy for customer needs.
• Strong knowledge of the Microsoft 365 ecosystem (SharePoint, OneDrive, Exchange, Teams) and experience with SaaS security and compliance practices.
• Experience in data backup and restoration, including recovery planning and the implementation of recovery strategies, is an asset.
• Good understanding of Disaster Recovery use cases and real-world scenarios where backup tools are critical.
• Excellent communication and influence skills, able to align technical and non-technical stakeholders, collaborate with Product and Design teams, and develop and mentor fellow developers.

Salary range: $140K–$180K CAD.
This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate’s region to align with local market conditions.

Job Description

So, what will your new role look like?

As a Senior Product Designer on ShareGate Migrate, you’ll work in a close product trio (PM, Tech Lead, Designer) to shape the experience of a product used in high-impact, operationally sensitive projects. You will design solutions that help IT administrators navigate complex migration scenarios with clarity and confidence. The work spans strategy and execution: defining problem spaces, shaping flows and interactions, refining UI details, and iterating quickly based on learning. You’ll thoughtfully explore where AI can enhance the experience and whether it’s simplifying planning, surfacing insights, or guiding teams through technical decisions. This is an opportunity to work on meaningful challenges that have a real impact on how organizations evolve their digital workplaces. You’ll thrive here if you enjoy complexity, collaborate naturally with engineers and PMs, and care about delivering dependable, thoughtful user experiences that scale.

Responsibilities: 

• Lead end-to-end design within your product team, from framing problems to refining final interactions;
• Turn ambiguous or technical workflows into intuitive, purposeful experiences for IT professionals;
• Design flows, interfaces, and interactions that simplify Microsoft 365 and cloud-migration scenarios;
• Collaborate closely with PMs, engineers, and subject-matter experts to clarify scope and align on strategy;
• Prototype, test, and iterate quickly to validate assumptions and strengthen solutions;
• Use data, customer feedback, and product insights to guide decisions and improve outcomes;
• Explore AI-driven opportunities that make migration and governance workflows more efficient, predictive, and reliable;
• Contribute to improving the design workflow with new tools, innovation, and new methodologies;
• Contribute to the evolution of our design system and help ensure consistency across ShareGate.

A typical week?   

You’ll move fluidly between strategic exploration, hands-on design, and close collaboration. Expect to:

• Shape product direction during trio planning and discovery activities;
• Translate customer needs and business opportunities into clear flows, wireframes, and prototypes;
• Partner with engineering to refine scope, understand constraints, and uphold design quality throughout development;
• Present in-progress work to teams and stakeholders for feedback during critiques and async reviews;
• Review migration data, support trends, and user behavior patterns to inform decisions;
• Refine interaction details and ensure thoughtful, cohesive hand-offs;
• Document rationale and communicate decisions effectively across teams;
• Utilize AI tools that increase your effectiveness in understanding our customers;
• Prototype with AI prototyping tools regularly to communicate, test, and validate solutions.

You’ll have autonomy, ownership, and a team that values thoughtful execution and continuous learning.

What does your future team look like?   

You’ll join a multidisciplinary team where designers are involved early, shape direction, and partner closely with engineering and product management. We care about clarity, rigor, and delivering experiences that genuinely help technical users succeed.
Design here is collaborative, feedback-rich, and committed to raising the bar both in process and craft.

What are the next challenges awaiting your team?   

ShareGate is evolving rapidly, and the design problems ahead require both creativity and structured thinking. You’ll help tackle:

• Enterprise-scale migration scenarios that push for clarity, predictability, and efficient execution;
• Modernization of core experiences across ShareGate Migrate and our broader ecosystem;
• A growing design system that supports new patterns, accessibility, and multi-product cohesion;
• AI-native planning and guidance to help IT teams anticipate risks and make informed decisions.

This is a role where you can influence not only how the product works today, but also how it evolves over the next several years.

Qualifications

• 6+ years designing B2B SaaS products within cross-functional teams;
• Strong user instincts and confidence navigating ambiguous, technically complex problem spaces;
• Proven ability to work across strategy, UX flows, UI design, and polished interaction details;
• Ability to balance speed, technical constraints, and high-quality execution;
• Experience designing for technical audiences (IT, admin tools, platforms) is a plus;
• Experience designing or contributing to AI-powered experiences;
• Clear communicator with strong storytelling skills, comfortable influencing product and engineering partners;
• High attention to detail and a deep commitment to craft.

Salary range: $120–$145k CAD.
This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate’s region to align with local market conditions.

Job Description

So, what will your new role look like?

As a Senior Product Designer on ShareGate Migrate, you’ll work in a close product trio (PM, Tech Lead, Designer) to shape the experience of a product used in high-impact, operationally sensitive projects. You will design solutions that help IT administrators navigate complex migration scenarios with clarity and confidence. The work spans strategy and execution: defining problem spaces, shaping flows and interactions, refining UI details, and iterating quickly based on learning. You’ll thoughtfully explore where AI can enhance the experience and whether it’s simplifying planning, surfacing insights, or guiding teams through technical decisions. This is an opportunity to work on meaningful challenges that have a real impact on how organizations evolve their digital workplaces. You’ll thrive here if you enjoy complexity, collaborate naturally with engineers and PMs, and care about delivering dependable, thoughtful user experiences that scale.

Responsibilities: 

• Lead end-to-end design within your product team, from framing problems to refining final interactions;
• Turn ambiguous or technical workflows into intuitive, purposeful experiences for IT professionals;
• Design flows, interfaces, and interactions that simplify Microsoft 365 and cloud-migration scenarios;
• Collaborate closely with PMs, engineers, and subject-matter experts to clarify scope and align on strategy;
• Prototype, test, and iterate quickly to validate assumptions and strengthen solutions;
• Use data, customer feedback, and product insights to guide decisions and improve outcomes;
• Explore AI-driven opportunities that make migration and governance workflows more efficient, predictive, and reliable;
• Contribute to improving the design workflow with new tools, innovation, and new methodologies;
• Contribute to the evolution of our design system and help ensure consistency across ShareGate.

A typical week?   

You’ll move fluidly between strategic exploration, hands-on design, and close collaboration. Expect to:

• Shape product direction during trio planning and discovery activities;
• Translate customer needs and business opportunities into clear flows, wireframes, and prototypes;
• Partner with engineering to refine scope, understand constraints, and uphold design quality throughout development;
• Present in-progress work to teams and stakeholders for feedback during critiques and async reviews;
• Review migration data, support trends, and user behavior patterns to inform decisions;
• Refine interaction details and ensure thoughtful, cohesive hand-offs;
• Document rationale and communicate decisions effectively across teams;
• Utilize AI tools that increase your effectiveness in understanding our customers;
• Prototype with AI prototyping tools regularly to communicate, test, and validate solutions.

You’ll have autonomy, ownership, and a team that values thoughtful execution and continuous learning.

What does your future team look like?   

You’ll join a multidisciplinary team where designers are involved early, shape direction, and partner closely with engineering and product management. We care about clarity, rigor, and delivering experiences that genuinely help technical users succeed.
Design here is collaborative, feedback-rich, and committed to raising the bar both in process and craft.

What are the next challenges awaiting your team?   

ShareGate is evolving rapidly, and the design problems ahead require both creativity and structured thinking. You’ll help tackle:

• Enterprise-scale migration scenarios that push for clarity, predictability, and efficient execution;
• Modernization of core experiences across ShareGate Migrate and our broader ecosystem;
• A growing design system that supports new patterns, accessibility, and multi-product cohesion;
• AI-native planning and guidance to help IT teams anticipate risks and make informed decisions.

This is a role where you can influence not only how the product works today, but also how it evolves over the next several years.

Qualifications

• 6+ years designing B2B SaaS products within cross-functional teams;
• Strong user instincts and confidence navigating ambiguous, technically complex problem spaces;
• Proven ability to work across strategy, UX flows, UI design, and polished interaction details;
• Ability to balance speed, technical constraints, and high-quality execution;
• Experience designing for technical audiences (IT, admin tools, platforms) is a plus;
• Experience designing or contributing to AI-powered experiences;
• Clear communicator with strong storytelling skills, comfortable influencing product and engineering partners;
• High attention to detail and a deep commitment to craft.

Salary range: $120–$145k CAD.
This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate’s region to align with local market conditions.

Job Description

So, what will your new role look like?

You’ll be joining a team of experienced developers who design and evolve widely used products. In this role, you’ll actively contribute to the development of complete features, from Front-End to Back-End, while taking part in both technical and product decisions. Beyond code, you’ll also be involved in discussions around customer value, performance, quality, and maintainability of the solutions.

Responsabilities:

• Design, develop, and maintain fullstack features using C# .NET and React;
• Work closely with the Product Manager and Product Designer to turn needs into real solutions;
• Work with SQL databases (primarily PostgreSQL), including data modeling and query optimization;
• Contribute to architectural decisions and development best practices;
• Ensure code quality through reviews, testing, and continuous improvement;
• Actively participate in both product and technical discussions within the team.

What does your future team look like?   

A multidisciplinary squad made up of 2 to 3 full-stack developers, a Product Manager, a Product Designer, and an Engineering Manager. The team is composed of experienced, product-oriented developers who care as much about the value delivered as the technical decisions behind it. We are currently looking to fill three Software Developer II positions to strengthen the team, increase our delivery capacity, and support the product’s evolution.

What are the next challenges awaiting your team?

 The main upcoming challenges will be tied to managing and leveraging large volumes of data. We will need to design efficient solutions that allow users to query, filter, and display this data smoothly and meaningfully. This will require both smart technical decisions around performance and user experience, as well as thoughtful data and interface architecture.

Qualifications

• 3+ years of experience in software development;
• Fullstack development experience;
• Proficiency in C# .NET;
• Experience with React;
• Solid understanding of SQL databases;
• Experience with PostgreSQL;
• Strong interest in product development.

Salary range: $95K–$125K CAD.
This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate’s region to align with local market conditions.

As part of our innovation efforts, we’re currently testing an AI phone screen agent for this role. You may be invited to answer a few initial questions via this agent. If your profile aligns with the role, a recruiter will follow up with you to schedule a call and discuss next steps. If we decide not to proceed after this stage, you’ll receive an email from a recruiter with our decision and we’ll also share feedback with you.