Doing business to business, person to person. Payworks is a leading workforce management solutions provider and multi-year winner of the Canada’s Best Managed Companies program. We are proudly Canadian and committed to developing world-class products and providing a progressive workplace culture where

Doing Right by People

is our purpose.

With clients of all sizes and nearly 700 employees, we currently have an exciting prospect on our Product Management team for the right candidate.

Because when it comes to great people, there’s always room for one more.

DOING RIGHT BY PEOPLE – IT’S WHAT WE DO Reporting to the Senior Manager, Product, the Team Lead, Product guides and develops a team of high-performing Associate Product Managers (APMs) working within Payworks’ AI Product Development Lifecycle (AI PDLC), the operating model that reflects Payworks’ commitment to building AI-enabled products. This is a player-coach position that combines hands-on product management expertise with people leadership. The Team Lead is responsible for developing each APM along a clear path toward the Product Manager role, building the capabilities it requires: running discovery, creating working prototypes, sequencing delivery into valuable increments, and shipping each release with the telemetry to prove it changed a user outcome.. They support the team’s professional growth, ensure high-quality output, and work closely with Product Managers, Designers, Developers, Business Analysts, Product Operations, and other cross-functional partners to enable strategic, AI-embedded, and outcome-driven product decisions.

WHY YOU SHOULD CHOOSE PAYWORKS

+Comprehensive employer paid benefits, including a Health Spending Account,



for you and your family and excellent pension plan with employer contributions.

+Plenty of professional development opportunities.

+Community-minded culture – Receive two paid days per year to volunteer and lots of opportunity to "Pay it Forward".

+Time and flexibility to meet your needs – Hybrid work model with flexible work options, plus 3 weeks vacation to start, flex time and parental leave benefits.

+Cool perks – Annual Lifestyle Spending Account, fun office environment and events, and more

BUILDING PRODUCT, GROWING PEOPLE – IT’S WHAT YOU’LL DO

+Coach and grow the team

– Own the day-to-day coaching, feedback and development of a team of Associate Product Managers. Set growth plans, give stretch assignments that let them run an initiative end to end, and own each person's path toward the Product Manager role.

+Set the standard for AI-assisted product work

– This is a player-coach role, so you stay hands-on. You'll model fluency in AI-assisted prototyping tools and coach your APMs to work directly from prototypes and shared context rather than requirement documents, promoting the tools, templates and frameworks that make the AI PDLC work at scale.

+Raise the quality bar

– Review and guide your team's discovery, prototypes, dev-ready bundles and telemetry plans for data accuracy, relevant insight, sound trust design and clear storytelling.



Coach them to sequence by riskiest assumption and keep a live micro-job pipeline running ahead of engineering.

+Shape what gets built

– Work with Product Managers and the wider product team to re-imagine the client's workflow, identify and prioritize the client and user problems worth solving, and make sure that prioritization lines up with Payworks' business goals.

+Champion the team and build the practice

– Act as the link between your APMs and the product and development teams, bring the team's voice into planning, and partner with Product Operations to codify what works into repeatable practice. Stay current on AI-enabled product management and the HCM industry, and bring what you learn back to the team.

WHAT YOU’LL NEED TO SUCCEED

+5+ years of B2B SaaS product management experience with a solid track record as a Product Manager, including products you shipped that changed a measurable user or business outcome. This hands-on experience is what lets you credibly develop APMs on their path to the PM role.

+A genuine appetite for developing people: you build capability and confidence through regular coaching and feedback, and you create a team environment where it's safe to experiment and learn.

+Fluency in at least one AI-assisted prototyping tool (Claude Code, Replit, Lovable, Cursor or equivalent), and comfort with data and telemetry tools such as SQL, Excel and BI platforms like Tableau or Power BI.

+Telemetry literacy, plus experience designing human-in-the-loop trust into AI-assisted product surfaces: confidence scoring, shadow-run onboarding, progressive-trust unlocks.

+Discovery and delivery fluency: JTBD, opportunity and

📌 Team Lead, Product (Winnipeg)
🏢 Payworks
📍 Winnipeg