Vice President scaling Plooto’s payment automation platform for SMBs through accountant-led distribution, direct sales, and strategic partnerships. Leading Sales and Partnerships to drive measurable customer growth.
Responsibilities
Build and scale Plooto’s commercial distribution engine
Turn accountants and bookkeepers into a scalable distribution channel
Strengthen the direct sales organization and develop strategic partnerships
Lead Sales and Partnerships & Business Development and report to the CEO as a member of the Executive Leadership Team
Build a repeatable accountant and bookkeeper distribution model
Turn institutional relationships into practitioner-level adoption through field coverage, enablement, incentives, and operating models
Set commercial strategy across accountant-led distribution, direct sales, strategic partnerships, and self-service
Build and develop sales and partnerships leaders while inspecting deals, partners, funnel performance, and customer reality
Originate, structure, negotiate, and expand strategic ecosystem partnerships
Use conversion, CAC, LTV, payback, sales productivity, partner activation, and downstream customer growth data to allocate investment
Collaborate across Marketing, Product, Data, Customer Operations, and Compliance
Engage with customers, prospects, accounting firms, practitioners, and major partners to inform strategy and product decisions
Communicate commercial performance, choices, and risks to the Executive Leadership Team and Board
Establish commercial strategy, improve partner activation and productivity, strengthen sales execution, develop partnerships, and build cross-functional operating rhythm
Requirements
Senior commercial leadership experience in a technology business serving small and medium-sized businesses
Evidence of personally building or materially scaling 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
Experience making disciplined choices about sales assistance and customer acquisition economics
Ability to lead both a sales organization and a strategic partnerships or business development function
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
Systems view of GTM and ability to create accountability across functions not directly managed
Executive judgment, clear communication, and confidence to challenge the CEO and peers constructively
Hands-on operating style suited to Plooto’s scale
Canadian market knowledge and a base in Canada
Experience building distribution through accountants, bookkeepers, tax professionals, accounting software ecosystems, or similarly trusted SMB advisors strongly preferred
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
Inclusive workplace commitment
Recruitment-process accommodation in accordance with applicable accessibility legislation
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