Hybrid Director of Field Sales

at Alternative Payments

• Job title: Director of Field Sales
• Job type: Full Time
• Experience level: Lead
• Salary: CA$150,000 - CA$180,000 per year
• Degree requirement: Bachelor's Degree
• Location requirements: Hybrid, Toronto, Canada

About the role

• Director of Field Sales at Alternative Payments overseeing event strategy and execution in the MSP sector. Building relationships and coaching teams for successful in-person engagements.

Responsibilities

• Own in-person events strategy across the MSP industry: which events we attend, what our commercial plan is at each, and how we measure success.
• Execute at events personally: booth selling, stage presentations, executive dinners, hallway conversations, and after-hours relationship building.
• Build the pre-event and post-event system: targeted outreach before each conference, structured follow-up afterward, and pipeline tracking tied to specific events.
• Develop AEs into conference sellers. Bring them to events, coach them on-site, debrief afterward, and build their confidence at in-person pipeline generation.
• Experiment with new event formats and tactics: different booth approaches, dinner structures, partnership activations, and regional meetup strategies. Measure results and iterate.
• Build a personal network within the MSP communities that generates referral pipeline and warm introductions.
• Collaborate with the Event Manager on logistics and the Director of Revenue Enablement on training materials, but own the commercial playbook and on-site execution.
• Report on event ROI with real numbers: pipeline generated, meetings booked, deals influenced, cost per opportunity.

Requirements

• 5–10 years in B2B SaaS or fintech sales with significant in-person and field selling experience.
• Familiarity with the MSP ecosystem and IT channel events.
• You’ve worked conferences, trade shows, and executive events — not just attended them.
• You’ve presented on stage to a room of 50–500 people and you’re good at it.
• A track record of building relationships that turn into pipeline.
• You’ve coached or mentored junior sellers on in-person selling skills, formally or informally.
• You’re systematic about events: you plan before, execute during, and follow up after. You track what works.
• Working knowledge of Salesforce for pipeline tracking.

Benefits

• Equity opportunities so you can share in our growth and success.
• Unlimited PTO and flexibility when you need it the most.
• Yearly learning & development stipend to help you grow and do your best work.