Homebase (YC W21)

Founding Sales Leader – SMB

Homebase (YC W21)

full-time

Posted on:

Location Type: Hybrid

Location: Toronto • Canada

Visit company website

Explore more

✨ AI Apply
Apply

Salary

💰 CA$230,000 per year

Job Level

Senior

About the role

  • Own a one-call-close motion (with follow-up for trials), targeting ~1–2 closes per rep/day (as the model stabilizes).
  • Set and manage activity + conversion inputs (connect rate, show rate, trial-to-paid, close rate, time-to-close).
  • Build the “daily operating system”: call QA, scorecards, pipeline hygiene, and weekly coaching cadence. Hire and ramp the first Toronto pod (3 reps in immediately), scale to ~9 reps in Q2, and ~15 reps in the plan as the model proves out
  • Builds the playbooks and motions for how we sell AI to owners who are skeptical, busy, and not “tech-first.”
  • Turns strong early signals from Toronto into a repeatable revenue engine for our AI hiring product
  • This is a builder role, not a maintenance role. The right person has taken a company from ~$1M to a few million in ARR, built a small team, and loves being close to product and customers

Requirements

  • 5–8+ years in B2B SaaS sales, with 3+ years leading a sales team (Manager, Head of Sales, or VP at a small startup)
  • Experience helping grow a product from early revenue (~$1M) to several million ARR through a high-velocity SMB Sales motion
  • Experience defining and implementing sales processes; wrangling “early chaos” to a repeatable, reliable revenue engine
  • Deep comfort with SMB, outbound-heavy sales motions (high activity, fast cycles, smaller ACVs)
  • Proven ability to hire, coach, and retain high-performing reps
  • Player-coach mindset — you jump on calls and into the details; you teach by doing
  • Metrics-driven and data-literate; you manage through insight, not vibes
  • Fast-moving, experimental, and biased to action
  • Collaborative partner across Product, Marketing, RevOps, and People
  • AI fluency
  • Comfortable selling AI-powered products to non-technical audiences
  • Able to explain AI clearly, responsibly, and practically to customers
  • Curious and proactive about using AI tools to improve sales workflows, coaching, and productivity
  • Uses AI daily for call review/QA, objection tagging, script iteration, and coaching plans.
  • Comfortable selling AI responsibly (sets expectations, avoids overpromising, communicates limitations clearly).
  • Runs experiments: A/B scripts, sequences, and onboarding prompts; measures lift and ships the winner.
  • Excited to experiment, measure impact, and continuously refine how AI is used in GTM
Benefits
  • Stock options + TFSA/RRSP with 4% company match
  • Comprehensive medical, dental, and vision for you and your dependents
  • Flex time off + company holidays + designated focus periods
  • Maternity/Parental Leave EI top-up support offered (after 6 months of service)
  • Work From Anywhere Month + meeting-free weeks yearly
  • Life insurance + short/long-term disability coverage
  • Meals provided, team offsites, and Customer Days
  • Monday through 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
B2B SaaS salessales processesrevenue growthmetrics-drivendata literacyAI fluencysales workflowsA/B testingcoaching planspipeline management
Soft Skills
leadershipcollaborationplayer-coach mindsetcuriosityproactivityexperimental mindsetcommunicationcoachingproblem-solvingadaptability