Founding Sales Leader - Hiring, SMB (Hybrid)

Hi, Future Homie!At Homebase, you’ll join a team that’s bold, fast-moving, and obsessed with helping small businesses thrive. We build with empathy, act with urgency, and take big swings that drive real-world impact. Here, every Homie shows up to raise the bar, support one another, and celebrate wins as a team.We’re investing heavily in an AI-powered hiring assistant that helps busy owners attract, screen, and hire great hourly talent. Toronto will be the home of a new sales hub focused on bringing this AI hiring product to thousands of small businesses.We’re not just building an app—we’re building unstoppable teams. So what do you say, are you in? 📍Your Impact Starts HereThis is not an enterprise/partnership role. It’s a high-velocity SMB motion where the team must close multiple deals per day. You will be expected to initially sell personally, build the operating system (process, dashboards, QA), and hire the first reps in Toronto. We’re looking for a founding sales leader in Toronto to build and lead a high-velocity outbound team selling our AI-powered hiring assistant to small, local businesses across North America, where customers are.This is a founding leadership role. You’ll take early traction in Toronto and turn it into a repeatable, scalable revenue engine for our AI Hiring product. You’ll hire and coach the first team of Hiring-focused reps, define how we sell AI to busy small business owners, and help shape the future of hiring at Homebase.This role blends builder, operator, and player-coach energy. You’ll be close to customers, close to the data, and close to the work.These are the key ways you’ll contribute and create impact in this 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 outBuilds 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 productThis 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🚀 The Foundation for Success - These are the experiences and strengths that will set you up for success in this role: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 motionExperience defining and implementing sales processes; wrangling “early chaos” to a repeatable, reliable revenue engineDeep comfort with SMB, outbound-heavy sales motions (high activity, fast cycles, smaller ACVs)Proven ability to hire, coach, and retain high-performing repsPlayer-coach mindset — you jump on calls and into the details; you teach by doingMetrics-driven and data-literate; you manage through insight, not vibesFast-moving, experimental, and biased to actionCollaborative partner across Product, Marketing, RevOps, and People✨AI fluencyComfortable selling AI-powered products to non-technical audiencesAble to explain AI clearly, responsibly, and practically to customersCurious and proactive about using AI tools to improve sales workflows, coaching, and productivityUses 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 experimen ... (truncated, view full listing at source)