Vice President, Commercial

• Company: Plooto
• Position: Vice President, Commercial Growth
• Location: Remote - Canada

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.

We are building the financial operations platform small and medium-sized businesses can rely on to run with greater control, efficiency, and confidence.

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.

• 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. Make clear choices about where we invest and why.
• 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. Understand conversion, CAC, LTV, payback, sales productivity, partner activation, and downstream customer growth.
• 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.
• Stay close to the market. Spend meaningful time with customers, prospects, accounting firms, practitioners, and major partners, and bring those insights into company strategy and product decisions.
• Contribute as an enterprise leader. Challenge assumptions, make clear tradeoffs, and communicate commercial performance, choices, and risks to the Executive Leadership Team and Board.

In your first year, you will have:

• 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…