Director of Field Sales

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

• We're seeking a Director of Field Sales to own in-person event strategy and execution across the MSP industry . You'll sell at conferences and events, build the system around them, and develop the AE team into strong conference sellers who can eventually run the playbook without you.
• NOTE:
• This is a fully remote position, open to folks currently living in the US or Canada.
• This role requires significant travel, including quarterly on-site visits to the Toronto office.
• 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.
• 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.

Benefits

Additional Information

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!

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