Founding Sales Leader, Homebase
Hiring, SMB
CA$230k
OTE
60/40 Split + Offers Equity
More information about location
4 days a week in office ( King Street West, ON)
Employee scheduling software for small businesses
Be an early applicant
Employee scheduling software for small businesses
1001+ employees
Be an early applicant
CA$230k
OTE
60/40 Split + Offers Equity
More information about location
4 days a week in office ( King Street West, ON)
1001+ employees
Company mission
To make local business teams unstoppable.
Role
Who you are
- 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
- 💡 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
- 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!
What the job involves
- 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
- 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
Application 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 🎉
Our take
Homebase provide employees and businesses with time tracking applications, with a range of other HR functionality built in. Homebase automates the process of managing employee scheduling, and also helps companies improve internal communications.
The company contributes to the reduction of paperwork in an office by turning an array of devices into time clocks that track hours and overtime, while also providing payroll support. This makes it easier for companies to remain in sync, running a more efficient operation as a result.
Given that Homebase's customer base of small businesses is not able to pay a lot for its product, scale is the key driver in the company's future success. With over 100,000 customers already, its significant venture capital backing will ensure that the company will be able to grow (notably it's investing in Canadian talent) to provide its services on a profitable scale.
Freddie
Company Specialist at Welcome to the Jungle
Insights
29% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Apr 2024
$60m
SERIES D
Nov 2021
$30m
GROWTH EQUITY VC
Total funding: $189m
Company benefits
- Stock Options
- Paid parental leave
- Generous paid time off options
- Offsites, customer days & social events
- Work from Anywhere Month
- Group health benefits coverage
- Group RRSP with employer match + TFSA
- Snacks + lunch on us at hub offices
- MasterClass at Work for ongoing learning
Company HQ
Yerba Buena, San Francisco, CA
Leadership
John Waldmann
(Founder & CEO)BA Political Science at Stanford. Associate at Boston Consulting Group, then KKR Capstone, before founding Homebase in 2014.
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