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.

About AlayaCare 

At AlayaCare, we’re more than just a fast-growing SaaS company, we’re a team of people passionate about transforming home healthcare. Our cloud-based platform empowers care providers around the world to deliver better outcomes for their clients.   

With 550+ employees across Canada, the US, Australia, and Brazil, we’re united by a shared mission and a strong culture of transparency, growth, and human connection. Whether you're early in your career or a seasoned expert, AlayaCare offers the opportunity to grow your impact, your skills, and your career.

About the Role

We are seeking a Manager, Software Development to join our Platform division. Reporting to the Director of Engineering, you will lead teams of Developers who are dedicated to product development and the ongoing enhancement of features within our SaaS application. By applying a deep understanding of the AlayaCare business, they ensure context and impact are clear, while driving accountability through ambitious yet realistic delivery plans.

As a Manager, Software Development you will cultivate a strong team identity while coaching and mentoring each team member. In the Platform division, the teams own the shared backend services and shared product features such as authentication, background jobs, configuration, integrations, eventing, notifications, roles and access control, organization hierarchy, secure messaging, document management, tasks, and data onboarding tooling.

What You’ll Do

People & Coaching

• Develop, foster and mentor a team of developers to deliver impactful solutions and grow their careers while driving the success of our platform.
• Motivate and support team members to achieve the targets
• Maintain proficient knowledge of industry trends and technology innovation
• Build and maintain a strong professional network to proactively source and attract top talent; serve as a brand ambassador for AlayaCare and own the end-to-end interview process while collaborating with the recruitment team
• Establish and execute impactful onboarding process to improve the team members’ experience.

Performance and delivery

• Accountable for delivering commitments and driving successful business results. Set direction and an operational model for the team(s) by anticipating strategic challenges, establishing processes, and business opportunities.
• Establish a high-performance culture by setting inspirational, measurable, and practical performance targets.
• Lead performance management and impact assessments for direct reports. Be accountable for the team(s)’s health and productivity.
• Translate business objectives into software delivery activities.

Technical and Operations

• Continuously define, prioritize, and execute technical initiatives to improve the reliability of systems managed by the team.
• Participate in architectural/technical design activities, code reviews and incident reviews, using them as opportunities to foster technical and process excellence.
• Actively code on a daily basis, leveraging AI-powered tools such as Claude or Cursor to stay at the forefront of AI capabilities and effectively support both the team and the broader organization
• Collaborate effectively with other teams and disciplines to solve interconnected problems and to ensure customer satisfaction.
• Establish, rollout, monitor, and continuously improve the technical and operational standards and best practices for the team(s).

What You Bring to the Team

• Bachelor’s or advanced degree in computer science, software engineering or related fields.
• Minimum 2+ years of people management experience in a technical industry, including strong cross-functional leadership
• and organizational skills.
• Excellent written and oral communication skills, with an ability to express technical and business concepts in
• approachable terms.
• Strong knowledge of contemporary software development practices, and opinions on how to best deploy them ((CI/CD, trunk-based development, feature flags, observability, test automation, incident response)
• Strong knowledge of AI-assisted development practices combined with a proactive approach to keeping pace with advancements and guiding teams in adopting them thoughtfully and effectively
• Experience with SaaS platforms and multi-tenant architectures is an asset.
• Bilingual in French and English

Why Join AlayaCare?  

Work With Purpose  

At AlayaCare, you’ll help build technology that empowers care providers and improves outcomes for patients and families. Every line of code and every customer interaction contributes to making care more connected, accessible, and human.  

Grow in a High-Trust Culture  

We believe in transparency, feedback, and assuming positive intent. Here, you’ll feel safe to share your ideas and career goals, and be supported to achieve them through mentorship, career mobility, and a promote-from-within philosophy.  

Balance That Works for You  

We value flexibility and well-being. From “Wellness Fridays” to volunteer time off, to flexible vacation, we make sure you have the space to recharge, contribute to your community, and live your best life.  

Benefits That Matter  

• Equity in a well-funded, scaling company.  
• Comprehensive health benefits, telemedicine, and lifestyle spending accounts.  
• Parental leave top-up and family support programs.  

Inclusive by Design  

We celebrate diverse perspectives and foster belonging through our DEIB initiatives. Employee-led events, summits, and social activities, both in-person and virtual, create meaningful connections across our global teams.  

AI at Work

At AlayaCare, AI is a core part of how we work. Success in this role requires bringing a working knowledge of AI, having used AI tools in practice, and being able to demonstrate how AI has helped improve the quality, efficiency, or impact of your work. We look for people who can adapt to new tools and ways of working and use AI responsibly in line with our privacy and security standards. We’ll support you with the tools, training, and coaching needed to succeed in an AI‑enabled environment.

Location and Work Model

This role is based in Montreal. At AlayaCare, our hybrid model includes 2 set in-office collaboration days/week, and it is expected that team members are present in the office on those days to foster connection, innovation, and teamwork.  

Ready to Join Us?  

Apply today and be part of a company that makes a real difference in the future of home and community care. Not the right role for you? Share this posting with someone who might be a great fit.  

AlayaCare uses AI tools during our hiring process to support fair, consistent, and objective decision-making. Some initial screening steps may be automated to help identify qualified candidates. If your application is declined automatically, you may request a human review.  

We’re committed to creating a workplace where everyone belongs. If you require accommodation during the application process, please reach out to careers@alayacare.com. 

Job Description

So, what will your new role look like?

In this role, you will be at the heart of the employee experience by providing reliable, human, and efficient IT support to all Workleap team members. You will handle a wide variety of technical requests, ranging from access and SaaS tools management to device administration, while ensuring fast, high-quality service.

On a daily basis, you will analyze and resolve technical issues while documenting and structuring information to improve team practices. You will actively contribute to the evolution of processes and tools by proposing initiatives aimed at enhancing efficiency and user experience.

You will collaborate with the team on incidents and ad hoc projects, while managing your priorities with discipline in a fast-evolving environment.

Responsibilities:

• Provide high-quality technical support and resolve IT requests within reasonable timeframes
• Manage access and licenses (creation, modification, and removal of user accounts and SaaS access)
• Identify and implement improvements to IT processes and user experience leveraging automation and AI tools
• Administer the device fleet using MDM tools such as Intune and Jamf
• Gather, clarify, and document relevant information for the team
• Conduct research, investigate issues, and propose initiatives to improve user experience and efficiency
• Collaborate with the IT team on incident resolution and ad hoc projects
• Define priorities and ensure effective time management

What does your future team look like?   

• You will join a collaborative, people-focused, and service-oriented IT team whose mission is to support Workleap employees daily by providing a seamless and efficient technology experience.
• The IT Support team works closely with other teams to quickly resolve issues, improve tools, and optimize processes. It values knowledge sharing, teamwork, and continuous improvement.
• In a constantly changing environment, the team plays a key role in evolving practices and systems, with a strong focus on user experience and operational efficiency.

What are the next challenges awaiting your team?   

• The IT Support team must continuously adapt its tools, processes, and ways of working to effectively support a growing number of users.
• One of the main challenges will be optimizing and automating the management of access, equipment, and requests in order to improve the speed and quality of service.
• The team aims to improve documentation, structure knowledge, and increase user autonomy, without compromising a smooth and human experience.
• Finally, it plays a key role in evolving the technological environment, particularly by leveraging MDM tools and SaaS solutions to enhance security, efficiency, and ease of use in day-to-day operations.

Qualifications

• 8+ years of experience in IT support or a related field;
• Demonstrated experience using AI tools or automation to improve efficiency or service quality in an IT context;
• Excellent interpersonal skills and strong customer service orientation;
• Excellent communication skills in both French and English (spoken and written);
• Expertise in troubleshooting Windows 11 and macOS;
• Experience managing SaaS access;
• Knowledge of Azure AD, Microsoft 365, and Azure PIM;
• Autonomy, resourcefulness, and initiative;
• Strong interest in artificial intelligence and its practical applications.

Salary range: $68K–85K 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.