Note: The job is a remote job and is open to candidates in USA. Payworks is a Canadian workforce management solutions provider that develops payroll and human capital management software for Canadian businesses. The Product Manager will own AI-first initiatives end-to-end, building prototypes, guiding delivery, designing trustworthy human-in-the-loop experiences, and measuring product outcomes and adoption.
Responsibilities
- Own an initiative end-to-end – You'll take one of our AI-first initiatives ) from first discovery conversation to measured adoption. You find the opportunity, make the business case in dollars, and decide what gets built
- Build the prototype yourself – Here, the prototype is the spec. You'll build working prototypes in Claude Code and our designers join you as co-creators to raise the ceiling on what you've made. Each prototype is complemented by a product brief outlining business context, non-functional requirements and business logic
- Design AI that people actually trust – Our products monitor, flag and guide, but they never make the call on their own. You'll design the confidence signals, review steps and accuracy history that move a payroll practitioner from watching the AI to relying on it
- Keep the pipeline ahead of the team – You'll break the work into small, well-specified pieces and stay a step ahead of engineering, partnering closely with Business Analysts and developers so they can build straight from your prototype
- Prove it worked – Every release ships with the measures built in to show whether it changed a real outcome, and every roadmap item traces back to one. The work doesn't end at launch
- Own adoption, not just launch – Getting the product used is your deliverable too. You'll work with Sales, Marketing, Support, Implementation and Finance on positioning, launch materials, and the case for why clients should trust it
Skills
- • 5–8 years in B2B SaaS product management, including products you shipped that measurably changed something for users or the business
- • Fluency with at least one AI-assisted prototyping tool (Claude Code, Replit, Lovable, Cursor or equivalent), plus prototypes you can walk us through
- • Sharp discovery and delivery instincts: you prioritize by risk rather than convenience, and you're happy working from prototypes and shared context instead of requirement documents
- • Comfort with measurement: you instrument what you ship and tell leading indicators from lagging
- • Sound judgment in ambiguity, and the ownership to carry deliverables, timelines and quality through every release
- • Clear, declarative writing in English, and a collaborative style that treats other teams as co-creators rather than requesters
- • An appetite for change: our operating model is still evolving, and you'll pick up new tools and methods as you go
- The Product Manager 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
- Some travel may be required
- • Canadian payroll or HCM experience, or product work in another regulated space like fintech, health, insurance or security
- • You've shipped an AI or ML product in production, including work on quality, evaluation or trust design
- • Comfort working in French, since we serve clients and meet payroll compliance requirements in both official languages (EN/FR)
Benefits
- Comprehensive employer paid benefits, including a Health Spending Account, for you and your family
- Excellent pension plan with employer contributions
- Plenty of professional development opportunities
- Two paid days per year to volunteer
- Hybrid work model with flexible work options
- 3 weeks vacation to start
- Flex time
- Parental leave benefits
- Annual Lifestyle Spending Account
- Fun office environment and events
- Option to work fully from the Payworks office in Winnipeg or on a hybrid work model
Company Overview