About the job
Greetings, Future Homie!
Join Homebase, where our team is dynamic, quick-paced, and dedicated to empowering small businesses. We innovate with compassion, act swiftly, and take bold steps that lead to meaningful change. At Homebase, every Homie is committed to elevating performance, supporting each other, and celebrating collective achievements.
We are making significant investments in an AI-driven hiring assistant designed to help busy owners attract, evaluate, and secure top-notch hourly talent. Our new sales hub in Toronto will focus on delivering this cutting-edge AI hiring solution to countless small businesses.
We are not simply creating an application; we are constructing unbeatable teams. So, are you ready to join us?
Your Impact Begins Here.
This role is not about enterprise partnerships; it is a fast-paced SMB environment where our team must close multiple deals daily. Initially, you will be expected to drive sales personally, establish operational frameworks (processes, dashboards, quality assurance), and recruit the first sales representatives in Toronto. We seek a founding sales leader to build and manage a high-velocity outbound team that markets our AI-powered hiring assistant to small, local businesses throughout North America.
This is a foundational leadership position. You will leverage early traction in Toronto to develop a replicable, scalable revenue stream for our AI Hiring product. You will recruit and mentor the inaugural team of hiring-focused representatives, define our sales approach for AI solutions aimed at busy small business owners, and influence the future of hiring at Homebase.
This position requires a blend of builder, operator, and player-coach qualities. You will have close interactions with customers, data, and operational tasks.
Key Contributions and Impact Areas:
Manage a streamlined one-call-close sales process (with follow-ups for trials), aiming for approximately 1-2 closes per representative daily (as the model stabilizes).
Establish and oversee activity and conversion metrics (connect rates, show rates, trial-to-paid conversions, close rates, time-to-close).
Develop the “daily operating system”: quality assurance for calls, scorecards, pipeline management, and weekly coaching routines. Recruit and onboard the initial Toronto sales pod (3 representatives immediately), expanding to approximately 9 representatives in Q2, and around 15 as the model demonstrates success.
Create playbooks and strategies for how to effectively sell AI to skeptical, busy, and non-tech-savvy owners.

