Vice President, Commercial Growth

This is a fully remote position, open to applicants in Canada.

📋 Description

• Develop and enhance Plooto’s commercial distribution framework.

• Transform accountants and bookkeepers into an efficient distribution channel.

• Fortify the direct sales team and establish strategic partnerships.

• Oversee Sales, Partnerships, and Business Development, reporting directly to the CEO as part of the Executive Leadership Team.

• Create a sustainable distribution model targeting accountants and bookkeepers.

• Convert institutional affiliations into practitioner-level engagement through field support, enablement, incentives, and operational strategies.

• Define the commercial strategy encompassing accountant-led distribution, direct sales, strategic partnerships, and self-service offerings.

• Cultivate and mentor leaders in sales and partnerships while evaluating deals, partnerships, funnel performance, and customer insights.

• Enhance forecasting, pipeline evaluation, CRM efficiency, coaching, capacity planning, and performance accountability.

• Initiate, structure, negotiate, and grow strategic ecosystem partnerships.

• Utilize metrics such as conversion rates, CAC, LTV, payback periods, sales productivity, partner engagement, and downstream customer growth to guide investment allocation.

• Collaborate with Marketing, Product, Data, Customer Operations, and Compliance teams.

• Interact with customers, prospects, accounting firms, practitioners, and major partners to shape strategy and product development.

• Report on commercial performance, decisions, and risks to the Executive Leadership Team and Board.

• Establish a commercial strategy, enhance partner activation and efficiency, boost sales execution, cultivate partnerships, and create a collaborative operational rhythm.

⛳️ Requirements

• Proven senior commercial leadership experience within a technology company focused on serving small and medium-sized enterprises.

• Demonstrated success in building or significantly scaling a commercial operation, distribution channel, or go-to-market capability from an early stage.

• Substantial experience with indirect, partner-led, channel-led, or advisor-influenced distribution models.

• Strong understanding of low-ACV, high-volume SMB economics.

• Experience in making strategic decisions regarding sales support and customer acquisition economics.

• Capability to lead both a sales organization and a strategic partnerships or business development initiative.

• Proven track record of converting partner relationships into active distribution channels and measurable customer growth.

• Solid grounding in sales leadership fundamentals, including forecasting, pipeline management, coaching, capacity planning, and performance oversight.

• Ability to identify whether commercial challenges arise from execution, product issues, marketing, operations, or market conditions.

• A holistic view of go-to-market strategies and the ability to foster accountability across non-directly managed functions.

• Executive-level judgment, effective communication skills, and the confidence to constructively challenge the CEO and peers.

• A hands-on operational style that aligns with Plooto’s scale.

• Familiarity with the Canadian market and residence in Canada.

• Preferred experience in building distribution through accountants, bookkeepers, tax professionals, accounting software ecosystems, or similarly trusted SMB advisors.

• 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.

🏝️ Benefits

• Commitment to an inclusive workplace.

• Accommodation during the recruitment process in accordance with applicable accessibility legislation.