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 Here

This 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 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

🚀 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 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

🤝  The Homie Way - These principles guide everything we do—from how we work and make decisions to how we show up for each other.

• 💡 Be Customer Obsessed – Solve problems with empathy and creativity.

• ⚡ Move Fast, Learn Fast – Experiment, take action, and grow every day.

• 🎯 Own Your Impact – Think big, focus on what matters, and make decisions you stand behind.

• 🏆 Master Your Craft – Excellence fuels impact—show up, step up, and make your mark.

• 🏅 Win Together – Put goals over roles, lead with trust, and connect to our mission and each other.

What We Offer

• 💰 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 through Thursday are our required in-office days—a time to move faster as a team, build deeper connections, make better decisions, and build together.

What to Expect During the Interview Process

• Meet the Talent Acquisition team, Ivana L.

• Meet the Hiring Manager, Ray S.

• Participate in a Talent Showcase

• Meet Cross-functional Partners

• Background Check + Offer Stage

• Welcome to the team, Homie 🎉

💜 Belonging at Homebase - We're committed to fostering a welcoming space where every Homie can be their full self. Experience comes in many forms—so if you're excited about this role, even if you don’t meet 100% of the qualifications, we encourage you to apply! 

Homebase will consider qualified applicants with criminal histories in a manner consistent with the San Francisco Fair Chance Ordinance.

👋 Hey, We’re Homebase

Unstoppable teams start here.

Homebase is the everything app for hourly teams—built to simplify the day-to-day and superpower local businesses. With tools for scheduling, time clocks, payroll, communication, HR, and more, we help teams stay connected and in control. Today, over 100,000 small (but mighty) businesses rely on us to make work radically easier. Together, we’ve tracked over a billion hours for 2.5+ million workers—and we’re just getting started.

At Homebase, we celebrate diversity and are proud to be an equal opportunity employer. We welcome all candidates and do not discriminate based on any legally protected status. If you need accommodations during the hiring process, please let us know—we’re committed to ensuring fair and equitable access for all.