Product Manager

Tech Manitoba; Winnipeg; Hybrid; CAD 90,000 - 130,000; Full time

Benefits offered by this job

Health Spending Account

Professional development opportunities

Volunteer days per year

Flexible work options

Lifestyle Spending Account

Team events

Job summary

Payworks is seeking a Product Manager to lead AI-first initiatives within its payroll and HCM platform. You’ll own discovery, prototyping and adoption, shaping regulated software for 40,000+ Canadian SMBs across jurisdictions in English and French.

The role sits in a hybrid Winnipeg setting with a strong emphasis on collaboration and measurable outcomes. You’ll design AI features that assist payroll professionals while keeping human oversight on regulatory decisions, and you’ll partner with

Qualifications

• 5–8 years in B2B SaaS product management.
• Fluency with at least one AI-assisted prototyping tool (Claude Code, Replit, Lovable, Cursor or equivalent).
• Sharp discovery and delivery instincts: prioritize by risk and work from prototypes with shared context.

Responsibilities

• Own an initiative end-to-end—from discovery through delivery to measured adoption.
• Build the prototype yourself and define business context and non-functional requirements.
• Design AI that people actually trust: monitor, flag and guide, with human-in-the-loop for regulated decisions.
• Keep the pipeline ahead of the team by breaking work into small, well-specified pieces and collaborating with analysts and developers.
• Prove it worked: ensure releases include measures showing real outcomes and trace roadmap items to value.
• Own adoption, not just launch: collaborate with Sales, Marketing, Support, Implementation and Finance on positioning and materials.

Skills

AI prototyping tool experience

Tools

Claude Code

Replit

Lovable

Cursor

Job description

Information Technology

Full-time- Permanent | Hybrid | Winnipeg, MB

Does this sound like the right fit for you?

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.

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

Doing Right By People – It’s What We Do

The Product Manager owns one or more AI‑first initiatives end-to-end — from discovery, through delivery, to measured adoption — inside Payworks' payroll and HCM platform. Payworks builds regulated software for 40,000+ Canadian SMBs across all 13 provincial and territorial jurisdictions, in English and French. This role turns that compliance depth into AI‑assisted products Canadian businesses trust: software that monitors, flags, and guides payroll and HR work while keeping a human in the loop on every decision that carries regulatory weight.

The Product Manager works as an individual contributor inside our AI Product Development Lifecycle (AI PDLC), building working prototypes, sequencing delivery into valuable increments that our design partners help shape along the way, and shipping each release with the telemetry to prove it changed a user outcome. This role stays ahead of the development team at all times.

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!

Discovering, Prototyping, Proving – It’s What You’ll Do

• 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.

What You’ll Need To Succeed

• 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.

Considered An Asset

• 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).

We are proud to support a Flexible Work Plan that recognizes the diverse needs and lifestyles of our people. 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.

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.

Payworks does not use artificial intelligence (AI) technologies in the screening, asessment or selection of applicants at any stage of the hiring process.

This posting is for an existing vacancy within our team.

Product Manager

Payworks Payroll Services

• 80 Payworks Way Winnipeg MB R3Y 2L5
• 204 779-0537
• Send Email
• Visit Website

Additional Postings available from Payworks Payroll Services

Marketing Performance & Analytics Specialist

Client Service Representative, Small Business (Bilingual EN/FR)

Business Directory News Releases Events Calendar Hot Deals Member To Member Deals Marketspace Job Postings Contact Us Information & Brochures Join The Chamber

Share

Print Email Facebook Twitter LinkedIn

Tell a Friend