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Plooto is an all-in-one payment automation platform serving 14,000+ companies with payables and receivables management. The company is building the financial operations platform for small and medium-sized businesses to run with greater control, efficiency, and confidence.
You will join as Vice President, Commercial Growth, reporting directly to the CEO as a member of the Executive Leadership Team. Your primary mandate is to build and scale Plooto's commercial distribution engine by turning accountants and bookkeepers into a scalable distribution channel while strengthening the direct sales organization and developing strategic partnerships.
Key responsibilities include:
• Build a repeatable accountant and bookkeeper distribution model with clear segmentation, activation, enablement, and coverage strategies to drive SMB adoption.
• Convert institutional relationships into practitioner-level adoption through field coverage, enablement, incentives, and operating models that generate downstream customer growth.
• Set Plooto's commercial strategy across accountant-led distribution, direct sales, strategic partnerships, and self-service, making clear investment choices.
• Lead and develop the Sales and Partnerships & Business Development teams, building strong leaders while remaining close to frontline execution, deal inspection, and customer reality.
• Raise sales execution rigor through forecasting, pipeline inspection, CRM discipline, coaching, capacity planning, and performance accountability.
• Build strategic partnerships into measurable distribution by originating, structuring, negotiating, and expanding relationships with accounting firms, financial institutions, platforms, and ecosystem partners.
• Use data and unit economics (conversion, CAC, LTV, payback, sales productivity, partner activation) to allocate commercial investment.
• Work cross-functionally with Marketing, Product, Data, Customer Operations, and Compliance to identify constraints and create accountability across functions.
• Stay close to the market through meaningful time with customers, prospects, accounting firms, practitioners, and partners, bringing insights into strategy and product decisions.
• Contribute as an enterprise leader, challenging assumptions, making clear tradeoffs, and communicating commercial performance and risks to the Executive Leadership Team and Board.
Success in year one means establishing a clear commercial strategy, increasing partner activation and downstream customer generation, building repeatable accountant channel foundations, improving conversion and productivity, enhancing forecast quality and sales execution, developing strategic partnerships into measurable sources of value, building stronger leadership, creating effective cross-functional operating rhythms, and providing evidence-based views on future commercial investments.
REQUIREMENTS:
• Senior commercial leadership experience in a technology business serving small and medium-sized businesses.
• Demonstrated track record of personally building or materially scaling a commercial motion, distribution channel, or GTM capability from an immature starting point—with clear evidence of systems, coverage models, partner motions, teams, and capabilities you created rather than inherited.
• 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 sufficient incremental value to justify its cost.
• Experience operating in businesses where customer economics require disciplined choices about sales assistance rather than relying on enterprise deal sizes.
• Ability to lead both a sales organization and a strategic partnerships or business development function.
• Proven 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.
• Ability to diagnose whether commercial problems sit in execution, product, marketing, operations, or the market itself.
• Systems view of GTM and ability to create accountability across functions you do not manage.
• Executive judgment, clear communication, and confidence to challenge the CEO and peers constructively.
• Hands-on operating style suited to a company of Plooto's scale.
• Canadian market knowledge and base in Canada.
STRONGLY PREFERRED:
• Experience building distribution through accountants, bookkeepers, tax professionals, accounting software ecosystems, or similarly trusted SMB advisors.
ALSO RELEVANT:
• Experience in SMB finance, payments, payroll, practice management, vertical SaaS, fintech, broker-led distribution, reseller networks, franchises, professional-services firms, or other intermediary-led commercial models.
