NOTE: We are not accepting candidates out of Canada at this time.
Location: Remote (Canada, preference for Ottawa or EST timezone)
Type: Full-time
Compensation: OTE: $140K–$150K CAD with accelerators for overperformance, structured as a 50/50 base-to-variable split. Equity is also available for the right candidate, tied to proven success and scaling the sales function.
Reporting to: CEO / CTO, Co-founder

WHAT YOU’LL DO

• Own the full sales cycle: prospect, cold-call, email, LinkedIn — get meetings and close MSP partners
• Hone our outbound messaging and test new plays until we find repeatability
• Partner with leadership to shape GTM, but drive outbound yourself without waiting on marketing leads
• Prove the model, then help us scale: document what works, hire the next reps, and build the function into a team
• Serve as the voice of sales: bring feedback on what lands, what stalls, and where we win to shape our GTM
• Leverage our sales tools — HubSpot Sales Enterprise, ZoomInfo, Arrows (sales rooms), and integrated workflows with Fellow AI Notetaker — to manage pipeline, engagement, and collaboration.

Our enablement model follows the principles of Training, Coaching, and Roleplay, with activities prioritized early and outcomes ramping over time. These KPIs reflect both leading and lagging indicators of AE success — they are ambitious goals we’ll coach you toward, not sink-or-swim gates:

• New Partner Conversations per Week: Minimum of 10 net-new MSP conversations generated through outreach, resulting in 3 meetings per week and 1 identified ICP.
• Pipeline Coverage: Maintain at least 3x quota pipeline by Day 60.
• Demo-to-Opportunity Conversion Rate: 40%+.
• MSP Signups (Closed-Won): 3+ in the first 90 days.
• Referral Loops Activated: 1 new loop per month (Okta or MSP-sourced).
• CRM Hygiene & Process Adherence: Accurate and complete HubSpot records.
• Partner Handoff: 100% of closed MSPs transitioned to Partner Success.
• Time to First Closed-Won: Within first 45 days.
• By 90 days: Running consistent demos, closing new MSPs, and feeding insights back into the playbook.
• By 6 months: Driving repeatable outbound success and building sustainable pipeline coverage