Manager, Software Development - Billing & Subscriptions Canada - Remote

Workleap Technologies inc.; Canada; Remote; CAD 100,000 - 130,000; Full time

Job summary

A leading company in employee experience software is seeking a Manager for Software Development, focusing on their Billing and Subscriptions domain. You'll lead a talented team to modernize their monetization infrastructure, ensuring performance, security, and scalability while fostering a culture of innovation and excellence.

Qualifications

• Proven experience managing software development teams, ideally in platform or backend service domains.
• Strong technical background with the ability to influence architecture and long-term strategy.
• Experience managing technical debt, improving service health, and leading DevOps practices.

Responsibilities

• Own and deliver through your team the design, development, reliability, and performance of key shared services.
• Drive high technical standards and architectural decisions focusing on performance, scalability, and security.
• Guide your team through complex modernization efforts and embrace innersource contribution models.

Skills

Team Management

Technical Leadership

Cross-Functional Collaboration

Agile Methodologies

DevOps Practices

Communication

Education

Bachelor's in Computer Science or related field

Job description

Manager, Software Development - Billing & Subscriptions

Company Description

Workleap builds practical employee experience software that makes work simpler.

Our products include Workleap , a simple employee experience platform to boost engagement, drive performance, and develop teams, and ShareGate by Workleap , a single, trusted out-of-the-box solution for fast and secure migration, adoption, and Copilot readiness—simplifying data management across Microsoft 365.

With over 20,000 happy customers in more than 100 countries, Workleap products are a must-have for businesses looking to create a more engaging and successful workplace.

Job Description

So, what will your new role look like?

As a Manager, Software Development in the Shared Services department, you will be at the core of Workleap’s platform evolution—creating solutions that span both the Workleap Platform and ShareGate by Workleap product lines. You will lead a high-performing development squad focused on building and maintaining mission-critical platform services—starting with our Billing & Subscriptions domain, with the potential to expand into other foundational services such as authentication, user profiles, and notifications.

This role blends deep technical leadership with strategic execution. You’ll partner closely with stakeholders across product, finance, and engineering to modernize our monetization infrastructure, enable reusable platform capabilities, and ensure teams across Workleap can innovate without reinventing the wheel.

You’ll champion service ownership, foster a strong DevOps culture, and coach your team through the complexities of platform modernization, innersource collaboration, and delivery at scale.

Responsibilities

• Own and deliver through your team the design, development, reliability, and performance of key shared services—beginning with Billing & Subscriptions, and growing beyond.
• Drive high technical standards and architectural decisions with a focus on performance, observability, scalability, security, and long-term maintainability.
• Guide your team through complex modernization efforts—such as evolving legacy billing logic into flexible, SaaS-ready systems—and future-proofing them for continued growth.
• Foster a culture of ownership, continuous improvement, and operational excellence—championing end-to-end responsibility across the development lifecycle.
• Partner with Product, Finance, and Security to align roadmaps, manage risk, and accelerate value delivery.
• Act as a strategic voice within the Shared Services leadership team, contributing to broader platform direction, reusable capabilities strategy, and driving adoption of AI in our work.
• Coach and grow developers through mentoring, performance feedback, and career development plans.
• Embrace and promote innersource contribution models, reviewing contributions from other teams and helping define clear quality gates.
• Lead backlog prioritization with clarity and impact, making confident tradeoffs and decisions in ambiguous situations.
• Monitor team capacity and service health metrics, using telemetry and feedback to drive improvements.

What does your future team look like?

You’ll begin by leading the Billing & Subscriptions squad, a group of talented developers with a clear mandate to evolve our monetization infrastructure.

You’ll join a collaborative management group within the Shared Services department, where leaders work together on scaling our platform, simplifying technical complexity, and enabling product squads to deliver faster and better.

What are the next challenges awaiting your team?

• Modernize ShareGate’s legacy licensing system, enabling experimentation with modern SaaS pricing models.
• Scale platform services for consistency and reliability across product lines, while reducing duplication.
• Strengthen service ownership practices, including robust observability, security, and incident response.
• Grow a developer ecosystem through innersource contributions and enablement practices that scale.
• Embed AI and engineering excellence into workflows, code quality, and delivery pipelines.

Qualifications

• Proven experience managing software development teams, ideally in platform or backend service domains.
• Strong technical background with the ability to influence architecture and long-term strategy.
• Track record of delivering complex infrastructure or monetization systems in SaaS environments.
• Skilled in mentoring, performance management, and creating a high-trust, feedback-driven team culture.
• Comfortable navigating ambiguity, making confident decisions, and prioritizing based on business impact.
• Strong cross-functional collaboration skills—especially with Product, Security, and Infrastructure.
• Experience managing technical debt, improving service health, and leading DevOps practices.
• Familiarity with Agile, Lean, and continuous delivery methodologies.
• Excellent communication and interpersonal skills.
• Previous experience as a software developer is highly preferred.

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

AtWorkleap, we build together, we trusteach other,and we support each other in success or failure. You will be able to express yourself, evolve and develop your creativity in an environmentthat 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 atWorkleap:
Phone Screen - Virtual Interview using Microsoft Teams - Work Sample - Job Offer

We are looking forward to getting to know you!

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