About the role

Founding Sales Leader driving AI-powered hiring assistant sales to small businesses. Leading a sales team in a high-velocity, growth-focused environment based in Toronto.

Responsibilities

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

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