Staff Product Manager, Scheduling (Hybrid)

Homebase; Toronto; Hybrid; CAD 100,000 - 140,000; Full time

Job summary

A leading app for small businesses in Toronto is seeking a Staff Product Manager for Scheduling. The role involves owning the scheduling ecosystem, leading AI-driven innovations, and ensuring high-quality outcomes. Ideal candidates will have over 8 years of product management experience, especially in AI or scheduling software. This role combines strategic leadership with hands-on execution in a hybrid work environment.

Benefits

Stock options + TFSA/RRSP with 4% company match

Medical, dental, and vision for you and dependents

Flexible time off + company holidays

Maternity/Parental Leave EI top-up support

Work From Anywhere Month

Life insurance + short/long-term disability coverage

Qualifications

• Proven experience launching intelligent or data-powered products.
• Strong track record leading cross-functional initiatives.
• Experience in workforce, scheduling, or operations software preferred.

Responsibilities

• Define and execute the multi-year vision for Homebase Scheduling.
• Drive AI innovation partnering with Data Science.
• Define metrics that matter and drive measurable revenue.

Skills

Product management

AI product strategy

Data-informed decision-making

Cross-functional leadership

Customer empathy

Education

8+ years of product management experience

Tools

AI, ML, or predictive systems

Scheduling software

Job description

Overview

Hi, Future Homie! At Homebase, you’ll join a team that’s bold, fast-moving, and obsessed with helping small businesses thrive. We build with empathy, act with urgency, and take big swings that drive real-world impact. Here, every Homie shows up to raise the bar, support one another, and celebrate wins as a team.

We’re not just building an app—we’re building unstoppable teams. So what do you say, are you in?

Impact Starts Here

We’re looking for a Staff Product Manager, Scheduling to own and advance the full scheduling ecosystem — the tools, data, and intelligence that power how small businesses staff their teams efficiently and confidently.

You’ll lead the evolution of our Scheduling Assistant, an AI-driven system that anticipates business needs, automates staffing, and empowers owners and employees alike. You’ll also own the quality of our core scheduling experience, ensuring we deliver reliability, usability, and delight to every customer. This role blends AI product strategy, data-informed decision-making, and empathy for hourly teams.

You’ll partner with Engineering, Data Science, and Design leaders to reimagine scheduling end-to-end — defining how AI transforms the experience of running a local business. This is a Staff-level role balancing strategic leadership, technical depth, and a hands-on approach to driving measurable, high-quality impact across a key product area.

Key contributions

• Lead Scheduling Strategy: Define and execute the multi-year vision for Homebase Scheduling — covering the full customer journey from planning to last-minute changes for owners, managers, and employees.
• Drive AI Innovation: Partner with Data Science to evolve Scheduling Assistant into an intelligent co-pilot that forecasts demand, recommends staffing, and auto-builds optimal schedules.
• Influence the Platform: Shape Homebase’s AI architecture and integrations to ensure Scheduling works with the Homebase Assistant, Time Tracking, Payroll, and Hiring.
• Own Outcomes: Define metrics that matter — utilization, staffing accuracy, adoption, customer satisfaction — and drive measurable revenue.
• Lead Cross-Functional Execution: Partner across Product, Design, and Engineering to deliver customer value at velocity, mentor PMs, and elevate product excellence.
• Champion Our Customers: Be the voice of small business owners and hourly workers, translating needs into intuitive, equitable solutions.
• Build for Scale: Leverage Homebase’s platform and data to build smarter models for every schedule.

The Foundation for Success

• 8+ years of product management experience, including 3+ years delivering large-scale, customer-facing products end-to-end.
• Proven experience launching intelligent or data-powered products, ideally with AI, ML, or predictive systems.
• Strong track record leading cross-functional initiatives blending product, design, data science, and engineering.
• Strategic thinker who thrives in ambiguity and drives clarity across teams.
• Experience in workforce, scheduling, or operations software preferred.
• Comfortable setting vision and diving deep — from strategy docs and prototypes to customer feedback.
• AI Fluency: Rework workflows with AI, partner with DS/ML teams, and measure AI’s business impact.

Hybrid Collaboration: Works in-office on Tue/Wed for strategy and collaboration, and remote for deep focus.

The Homie Way

• Be Customer Obsessed — Solve problems with empathy and creativity.
• Move Fast, Learn Fast — Experiment, take action, and grow every day.
• Own Your Impact — Think big, focus on what matters, and make decisions you stand behind.
• Master Your Craft — Excellence fuels impact; show up, step up, and make your mark.
• Win Together — Put goals over roles, lead with trust, and connect to our mission and each other.

What We Offer (United States)

• Ownership & Financial Security: Stock options + 401(k) with 4% match
• Comprehensive Healthcare: Medical, dental, and vision coverage + FSA options
• Flexible Time: Unlimited PTO (salaried) + company holidays
• Family Support: Up to 12 weeks of paid parental leave (after 6 months of service)
• Protection Plans: Life insurance + short/long-term disability coverage
• Work From Anywhere Month + meeting-free weeks yearly
• Workspace Perks: Meals provided, commuter benefits, team offsites, and Customer Days
• Hybrid Rhythm: Tuesday and Wednesday are in-office days

What We Offer (Canada)

• Ownership & Savings: Stock options + TFSA/RRSP with 4% company match
• Health & Wellness: Medical, dental, and vision for you and your dependents
• Time Flexibility: Flex time off + company holidays + designated focus periods
• Family Support: Maternity/Parental Leave EI top-up support after 6 months
• Work Your Way: Work From Anywhere Month + meeting-free weeks yearly
• Protection Plans: Life insurance + short/long-term disability coverage
• Workspace Perks: Meals provided, team offsites, and Customer Days
• Hybrid Rhythm: Tuesday and Wednesday in-office days

Interview Process

• Meet Talent Acquisition team and Hiring Manager, with a Talent Showcase
• Meet Cross-functional Partners
• Background Check + Offer Stage
• Welcome to the team

Belonging at Homebase — We foster a space where every Homie can be their full self. If you’re excited about this role, we encourage you to apply!

Homebase will consider qualified applicants with criminal histories in a manner consistent with the San Francisco Fair Chance Ordinance.

About Homebase

Homebase is the everything app for hourly teams, offering scheduling, time clocks, payroll, communication, HR, and more. We rely on over 100,000 small businesses and 2.5 million workers to make work easier. We are an equal opportunity employer and welcome all candidates. If you need accommodations during the hiring process, please let us know.