Director of Field Sales

Alternative Payments

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.

Posted 5/5/2026full-timeToronto • 🇨🇦 CanadaLead💰 CA$150,000 - CA$180,000 per yearWebsite

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

B2B salesfield sellingevent strategypipeline trackingrelationship buildingcoachingmentoringevent executionpresentation skillsevent measurement

Soft Skills

networkingcommunicationleadershiporganizational skillsstrategic planningadaptabilitycollaborationconfidence buildingsystematic approachrelationship management