Director of Field Sales

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! What We re Looking For We re seeking a Director of Field Salesto 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. The other half of the job is coaching. You set the standard for how AP shows up at a conference - how to work a room, how to run a booth conversation that leads somewhere, how to present on stage, how to turn a badge scan into a qualified meeting. You bring AEs to events, coach them in real time, and debrief afterward. Over time, the team should be able to execute the playbook without you at every event. Community matters in this role. The MSP world runs on relationships and referrals. You ll build a personal network within these communities that generates warm introductions, referral pipeline, and the kind of trust that makes people take a meeting because they know you, not because they got a cold email. 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. What You ll Do • 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. What You ll Bring • 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. What We Offer • Competitive salary tailored to your experience, skills, and expertise. • The total compensation range for this role is $160,000 - $195,000 CAD (OTE), plus equity. The range displayed on each job posting reflects the approximate total target compensation for the position. Within the range, individual pay is determined by factors including relevant skills, experience, education/training. • 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. Why Choose Alternative Payments? At Alternative Payments, you ll do...