Vice President, Commercial Growth in Winnipeg

Plooto is an all-in-one payment automation platform that helps businesses and accounting firms manage payables and receivables. More than 14,000 companies use Plooto to automate financial workflows, move money, and reconcile with their accounting systems.

Plooto is looking for a Vice President, Commercial to build and scale our commercial distribution engine. Your primary growth mandate is to turn accountants and bookkeepers into a scalable distribution channel for Plooto, while strengthening our direct sales organization and developing strategic partnerships that create meaningful customer growth. You will lead Sales and Partnerships & Business Development and report directly to the CEO as a member of Plooto’s Executive Leadership Team.

This is a high-volume, low-ACV SMB business. Success requires strong judgment about where human sales effort creates value, where customers should move through self-service, and how trusted intermediaries can create efficient, repeatable distribution. We are looking for a builder. You will have personally created or materially scaled a commercial motion, channel, or capability from an immature starting point, while also bringing the operating discipline to lead and develop a strong sales organization.

What you will do:

• Build a repeatable accountant and bookkeeper distribution model.
• Determine how we identify, segment, enable, activate, cover, and grow the firms and practitioners that can drive meaningful SMB adoption.
• Turn institutional relationships into practitioner-level adoption.
• Build the field coverage, enablement, incentives, and operating model required to move from signing accounting firms to generating repeatable downstream customer growth.
• Set Plooto’s commercial strategy across accountant-led distribution, direct sales, strategic partnerships, and self-service.
• Lead and develop Sales and Partnerships & Business Development.
• Build strong leaders beneath you while remaining close enough to frontline execution to inspect deals, partners, funnel performance, and customer reality directly.
• Raise sales execution rigor through forecasting, pipeline inspection, CRM discipline, coaching, capacity planning, and performance accountability.
• Build strategic partnerships into measurable distribution.
• Personally help originate, structure, negotiate, and expand relationships with accounting firms, financial institutions, platforms, and other ecosystem partners.
• Use data and unit economics to allocate commercial investment.
• Work across Marketing, Product, Data, Customer Operations, and Compliance to identify and remove constraints across the customer journey and create accountability across functions you do not manage.
• Spend meaningful time with customers, prospects, accounting firms, practitioners, and major partners, and bring those insights into company strategy and product decisions.
• Challenge assumptions, make clear tradeoffs, and communicate commercial performance, choices, and risks to the Executive Leadership Team and Board.

What success looks like:

• Established a clear commercial strategy defining the roles of accountant-led distribution, direct sales, strategic partnerships, and self-service.
• Increased the number and productivity of activated accounting and bookkeeping partners and the downstream customers they generate.
• Built the foundations of a repeatable accountant channel, with clear segmentation, activation, enablement, coverage, and measures of partner productivity.
• Improved conversion and commercial productivity while maintaining disciplined customer acquisition economics.
• Improved forecast quality, pipeline visibility, sales execution, and performance accountability.
• Developed strategic partnerships into measurable sources of customers, revenue, or strategic value.
• Built stronger Sales and Partnerships leadership, with capable leaders able to run their areas with increasing independence.
• Created an effective cross-functional operating rhythm that turns market insight and funnel data into clear decisions, owners, and action.
• Given Plooto an evidence-based view of where to make its next commercial investments.

What you bring:

• Senior commercial leadership experience in a technology business serving small and medium-sized businesses.
• Clear evidence that you personally built or materially scaled a commercial motion, distribution channel, or GTM capability from an immature starting point.
• Meaningful experience with indirect, partner-led, channel-led, or advisor-influenced distribution.
• Strong judgment about low-ACV, high-volume SMB economics and where human sales effort creates enough incremental value to justify its cost.
• Experience operating in a business where customer economics require disciplined choices about sales assistance rather than relying on enterprise deal sizes to support an expensive acquisition model.
• The range to lead both a sales organization and a strategic partnerships or business development function.
• A record of turning partner relationships into active distribution and measurable customer growth.
• Strong sales leadership fundamentals, including forecasting, pipeline management, coaching, capacity planning, and performance management.
• The ability to diagnose whether a commercial problem sits in execution, product, marketing, operations, or the market itself.
• A systems view of GTM and the ability to create accountability across functions you do not manage.
• Executive judgment, clear communication, and the confidence to challenge the CEO and your peers constructively.
• A hands-on operating style suited to a company of Plooto’s scale.
• Canadian market knowledge and a base in Canada.

Why Become a Plootonian?

If you’re looking to make a meaningful impact, look no further. We’re transforming the payments space in North America by delivering an unrivalled product experience that solves a real and pressing problem for SMBs. One of the biggest challenges small businesses face is managing their finances and cash flow—and Plooto helps address that. We have strong product-market fit, a significant opportunity ahead, and the backing of experienced fintech leaders. You’ll join a team that cares deeply about customer impact, takes pride in its craft, and moves with urgency. We’re just getting started, and you’ll help shape the next chapter of our growth story. Join Plooto and be part of a mission that matters.

Our Commitment to Inclusion:

Plooto is committed to building an inclusive workplace where people of all backgrounds, experiences, and perspectives can thrive. We know great teams are built through diverse thinking, and we encourage you to apply even if your experience does not align perfectly with every qualification listed. Accommodation is available throughout the recruitment process in accordance with applicable accessibility legislation. If you require accommodation at any stage, please let us know—we’re happy to work with you.