Homebase (YC W21)

VP of Sales

Homebase (YC W21)

full-time

Posted on:

Location Type: Hybrid

Location: Toronto • Canada

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Job Level

Lead

About the role

  • Raise sales throughput (top priority): set the operating rhythm, targets, and coaching cadence that improves weekly output (activity → pipeline → closes).
  • Lead, coach, and develop sales managers: build a team of player-coaches who run tight floors, strong 1:1s, and consistent performance management.
  • Build and scale a high-energy sales culture: bring urgency, positivity, and clarity—creating an environment where high standards are normal.
  • Own hiring quality at scale: design and continually improve hiring processes for reps and managers; raise the bar while keeping velocity.
  • Run a metrics-first operating system: define the scorecard (inputs + outputs), review it daily/weekly, and translate data into clear actions fast.
  • Drive operational excellence: strengthen process adherence, forecasting hygiene, pipeline integrity, and territory/routing where relevant.
  • Partner cross-functionally: work closely with RevOps, Enablement, Marketing, Product, and CS to remove friction, improve conversion, and speed up learning loops.
  • Use AI to increase leverage: identify repetitive work that AI/automation can eliminate; help the team adopt tools that improve productivity and consistency.

Requirements

  • Proven VP-level leadership in high-velocity SMB / inside sales environments (high volume, high activity, fast learning cycles).
  • Demonstrated ability to improve measurable outcomes (e.g., conversion rates, pipeline velocity, rep ramp time, quota attainment, team throughput).
  • Strong outbound experience (even if inbound is strong today) and comfort running mixed motions.
  • Deep fluency in sales fundamentals and metrics—able to diagnose “what’s breaking” quickly and fix it with focused initiatives.
  • Hiring excellence at scale: you can spot real talent beyond interview polish and build a consistent, fair hiring process.
  • Coaching obsession: you run coaching like a daily practice, not an occasional meeting.
  • AI fluency for leaders: you don’t need to build models, but you do need to operationalize AI—retool workflows, measure impact, and coach your org on adoption.
  • Ability to collaborate in-office per our hybrid schedule (Mon–Thurs in-office at a Homebase hub). Relocation is expected for non-hub hires unless an exception is approved.
Benefits
  • 💰 Ownership & Savings: Stock options + TFSA/RRSP with 4% company match
  • 🏥 Health & Wellness: Comprehensive 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 offered (after 6 months of service)
  • 🌟 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
  • 💼 Our Hybrid Rhythm: We believe collaboration drives impact. That’s why Monday-Thursday are our required in-office days.
Applicant Tracking System Keywords

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

Hard Skills & Tools
sales metricspipeline managementcoachinghiring processesoperational excellencedata analysisAI adoptionperformance managementforecastingconversion rate improvement
Soft Skills
leadershipteam developmentcollaborationcoaching obsessioncommunicationurgencypositivityclarityadaptabilityproblem-solving