Homebase (YC W21)

Staff Product Manager, Scheduling

Homebase (YC W21)

full-time

Posted on:

Location Type: Hybrid

Location: Toronto • 🇨🇦 Canada

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Salary

💰 $184,000 - $252,000 per year

Job Level

Lead

About the role

  • Define and execute the multi-year vision for Homebase Scheduling.
  • Partner with Data Science to evolve our Scheduling Assistant into an intelligent co-pilot.
  • Shape Homebase’s broader AI architecture and integrations.
  • Define metrics that matter and drive measurable revenue.
  • Partner across Product, Design, and Engineering to deliver customer value at velocity.
  • Be the voice of small business owners and hourly workers.
  • Leverage Homebase’s platform and data to build models that get smarter with every schedule created.

Requirements

  • 8+ years of product management experience, with 3+ years driving large-scale, customer-facing products end-to-end.
  • Proven success launching intelligent or data-powered product experiences, ideally with AI, ML, or predictive systems.
  • Strong track record of leading cross-functional initiatives that blend product, design, data science, and engineering.
  • Strategic systems 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 writing strategy docs, to building prototypes, to debugging customer feedback.
  • AI Fluency: You retool workflows with AI, partner fluently with DS/ML teams, and measure AI’s business impact.
Benefits
  • Stock options + 401(k) with 4% match
  • Comprehensive Healthcare: Medical, dental, and vision coverage + FSA options
  • Unlimited PTO (salaried) + company holidays
  • Up to 12 weeks of paid parental leave (after 6 months of service)
  • Life insurance + short/long-term disability coverage
  • Work From Anywhere Month + meeting-free weeks yearly
  • Meals provided, commuter benefits, team offsites, and Customer Days

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
product managementAImachine learningdata-powered product experiencespredictive systemsmetrics definitionprototypingdebugging
Soft skills
strategic thinkingcross-functional leadershipcommunicationclarity in ambiguitycustomer advocacy
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