Director of Field Sales

Alternative Payments•Toronto, ON

5d•Remote

About The Position

Alternative Payments is building the financial operating system for SMBs, consolidating the disconnected tech stack that holds service-based businesses back. Starting with MSPs, we’ve spent five years perfecting accounts receivable, and we’re now expanding into accounts payable, AI-powered analytics, and beyond. We’re at an inflection point: closing the loop on money movement and laying the foundation for a platform that will reshape how service businesses operate financially. We’re growing fast, thinking big, and building a global team that wants to be part of something that lasts. We believe the best solutions come from diverse perspectives, deep collaboration, and a shared obsession with customer impact. If you’re energized by real problems, real customers, and real impact, we want to hear from you!

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 know the difference between showing up and executing.
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 — the kind where people take your call because they met you at an event two years ago.
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.

Nice To Haves

Experience building event ROI measurement frameworks.
Track record developing junior sellers into independent conference representatives.
Comfort working in fast-paced, dynamic, and high-impact environments.

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.