Founding Sales Leader - Hiring, SMB (Hybrid)

📋 Description

• Own a one-call-close motion; ~1–2 closes per rep/day.
• Set and manage activity + conversion inputs (connect rate, show rate, trial-to-paid, close rate).
• Build the daily operating system: QA calls, scorecards, pipeline hygiene, weekly coaching.
• Hire and ramp the first Toronto pod (3 reps immediately).
• Build playbooks and motions to sell AI to skeptical, busy owners.
• Turn early signals from Toronto into a repeatable revenue engine for our AI hiring product.

🎯 Requirements

• 5–8+ years in B2B SaaS sales; 3+ years leading a sales team.
• Experience growing product from early revenue (~$1M) to several million ARR via SMB sales.
• Experience defining and implementing sales processes; wrangling early chaos to a repeatable 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.
• AI fluency; able to sell AI-powered products to non-technical audiences; data-driven mindset.

🎁 Benefits

• Stock options + TFSA/RRSP with 4% company match.
• Comprehensive health, dental, and vision for you and dependents.
• Flexible time off + designated focus periods.
• Maternity/Parental Leave EI top-up support after 6 months.
• Work From Anywhere Month + meeting-free weeks yearly.
• Hybrid Rhythm: Mon–Thu in-office days.