Director of Field Sales

About the role

You will own the in-person event strategy for the MSP industry from end to end, deciding which conferences to attend and what commercial approach to run at each one. You will execute those events yourself, selling at booths, delivering stage presentations, hosting executive dinners, and building hallway relationships that turn into pipeline. You will build a repeatable system around conference attendance, from pre-event outreach to structured post-event follow-up and rigorous pipeline tracking. You will coach AEs to become confident conference sellers, working alongside them in real time on-site until they can run the playbook independently. You will cultivate a personal network inside the MSP community that generates warm introductions and a referral pipeline rooted in long-term trust.

Key facts

What you'll do

• Own the in-person events strategy across the MSP industry, selecting the right conferences and defining a measurable commercial plan for each.
• Execute at events personally, including booth selling, stage presentations, executive dinners, and informal hallway conversations that build trust.
• Build a pre-event and post-event system, with targeted outreach ahead of conferences and structured follow-up afterward tied to specific events.
• Develop AEs into conference sellers by bringing them to events, coaching them on-site, and debriefing afterward to build their confidence.
• Experiment with new event formats and tactics, such as different booth approaches, dinner structures, partnership activations, and regional meetups, then measure results and iterate.
• Build a personal network within MSP communities that generates warm introductions and a strong referral pipeline over time.
• Collaborate with the Event Manager on logistics and the Director of Revenue Enablement on training materials, while owning the commercial playbook and on-site execution.
• Report on event ROI using real numbers, including pipeline generated, meetings booked, deals influenced, and cost per opportunity.
• Maintain consistent documentation of event learnings and best practices so the playbook can be reused and improved.
• Partner with marketing to align event messaging with broader campaigns and ensure cohesive positioning across channels.
• Track leading and lagging indicators for each event to understand what drives high-quality pipeline and revenue.
• Mentor junior sellers on in-person techniques, helping them develop the skills to run booths and stage presentations confidently.
• Qualify and route event-generated pipeline to ensure timely follow-up and alignment with sales and customer success.
• Evaluate new event opportunities based on strategic fit, audience quality, and potential long-term value to the business.
• Drive continuous improvement by analyzing what works, discarding what does not, and doubling down on high-performing event approaches.

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 have worked conferences, trade shows, and executive events - not just attended them - and you know the difference between showing up and executing.
• You have presented on stage to a room of 50-500 people and you are good at it.
• You have a track record of building relationships that turn into pipeline, with people who take your call because they met you at an event years ago.
• You have coached or mentored junior sellers on in-person selling skills, formally or informally.
• You are systematic about events, planning before, executing during, and following up after, while tracking what works.
• You use Salesforce for pipeline tracking and are comfortable managing complex deal information.
• You are legally authorized to work in the country where you reside, with proof of eligibility required at the time of hiring.
• You are currently based in the US or Canada, given the fully remote nature of this role.

Nice to have

• 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.

Practical notes

This role is fully remote and open to individuals currently living in the US or Canada. It requires significant travel, including quarterly on-site visits to the Toronto office.