Team Lead, Product

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 opportunity 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 solution thinking, outcome-based road mapping, and prioritization by risk rather than convenience.

+ Strong strategic, analytical and critical thinking, with the ability to turn data into insight people can act on.

+ Excellent written and verbal communication, and the storytelling to connect your team's work to what the business is trying to achieve.

+ Comfort in a fast-paced, agile environment with many stakeholders and an evolving operating model.

Considered an asset:

+ Prior experience in a formal leadership role.

+ Canadian payroll or HCM experience, or product work in another regulated space such as fintech, health, insurance, legal or security.

+ Hands-on experience shipping AI products to production, including conversational AI or AI agents. Knows how to work with data science and engineering teams to have real conversations about model trade-offs, capability boundaries, and what it takes to get something into production responsibly.

+ Experience shipping an AI- or ML-informed product in production, including hands-on work writing and running evals, assessing model quality, and contributing to trust design. Bonus if you have coached others on how to build and interpret evals as part of a team workflow.

+ Familiarity with product management tools such as Jira, Confluence and Figma.

We are proud to support a Flexible Work Plan that recognizes the diverse needs and lifestyles of our people. The Team Lead, Product has the option to work fully from the Payworks office in Winnipeg or on a hybrid work model, working in the office at least three (3) days a week.

Payworks is committed to providing an inclusive, accessible environment, and collaborating with employees, clients and guests to identify and effectively remove barriers, in a manner that respects the principles of independence, dignity, integration, reasonable accommodation and equal opportunity. Payworks welcomes and encourages applications from all persons. Individuals applying for employment with Payworks may request accommodations at all stages of recruitment and employment from Human Resources.

Employees at Payworks’ come from different backgrounds, and we celebrate those differences. We are looking for the best candidate for this opportunity, but do not expect applicants to meet every qualification in order to be considered.

We may use AI-assisted tools for organization, sorting, and workflow management — however, we pride ourselves on a high-touch, human-centered process

This posting is for an existing vacancy within our team.