Head of Sales, SMB

Scale and optimize our phone-based, outbound sales engine that currently drives the majority of new business. - Ensure teams are executing with excellence on call quality, talk time, sequences, objection handling, and deal progression. - Implement and refine playbooks, scripts, talk tracks, and cadences designed for high-velocity environments. - Continuously improve funnel performance through testing and data-driven decision-making. ### 3. Drive Up-Market Expansion & AE Headcount Growth

Build and execute a strategy to move up-market, including targeting larger fleets and more complex accounts. - Recruit, hire, and ramp 20+ Account Executives in the next 6 months, ensuring the right mix of SMB, Mid-Market, and upmarket capabilities. - Partner with Marketing, Product, and RevOps to align ICP, messaging, packaging, and pricing with our upmarket strategy. - Develop differentiated sales motions for larger, more complex customers while maintaining our strong SMB foundation. ### 4. Build and Scale Expansion, Cross-Sell, and Account Management

Design and refine a structured expansion and cross-sell motion focused on driving multi-product adoption and increasing share of wallet. - Build out a robust Account Management function responsible for ongoing relationship management, strategic account planning, and retention. - Define success metrics and operating rhythms for account managers (e.g., renewal health, expansion pipeline, NRR). - Ensure tight coordination between New Business, Account Management, Customer Success, and Support. ### 5. Team Leadership: Recruiting, Culture, Training, Coaching, Accountability

Lead, mentor, and develop a team of 6 sales leaders and 55+ ICs, across both FTE and BPO teams. - Own recruiting and selection for your org, ensuring we hire talent that matches our low ego, high performance, high standards culture. - Create and reinforce a culture of brilliance in the basics: consistent activity, crisp follow-through, clean pipeline hygiene, and high-quality customer interactions. - Implement robust onboarding, training, and ongoing coaching programs to continuously elevate performance. - Hold teams and leaders accountable to clear standards, with transparent performance management and rapid course correction where needed. ### 6. Systems Thinking & Revenue Operations Partnership

Operate as a systems thinker, designing processes and structures that scale efficiently rather than relying on heroics. - Partner closely with Revenue Operations to ensure our CRM, reporting, territory design, compensation plans, and sales tooling support our strategy. - Instrument the revenue engine with clean data, reliable dashboards, and actionable insights that inform daily execution and strategic decisions. - Lead or support initiatives to improve conversion, reduce friction in the sales process, and shorten time-to-value for new customers. ### 7. Cross-Functional Leadership & Executive Collaboration

Collaborate with Marketing on demand generation, campaign strategy, and lead quality. - Partner with Product and Operations to bring market insights back into the roadmap and ensure we are solving the most important problems for our customers. - Work closely with the executive team on strategic planning, goal setting, and company-level priorities related to growth and profitability. - Represent Sales and Revenue as a key voice in discussions on company strategy, resourcing, and investment. About you:

10+ years of experience in B2B sales, with at least 5+ years leading large, outbound-centric sales organizations. - Demonstrated success leading high-velocity, phone-based outbound teams selling to SMB and Mid-Market customers. - Proven track record of owning the full revenue funnel (Acquisition, Activation, Expansion, Retention) and hitting or exceeding aggressive growth targets. - Experience managing managers and leading organizations of comparable scale (e.g., 5–10 frontline managers and 40+ ICs). - Hands-on experience building and scaling sales teams quickly, including hiring and ramping significant AE headcount in compressed timeframes. - Strong systems thinking capability: you design processes, structures, and operating rhythms that scale predictably. - Deep comfort with data and metrics: pipeline analysis, conversion funnels, capacity planning, headcount modeling, and forecasting. - Demonstrated ability to recruit, develop, and retain high-performing talent and to build a culture of high standards, accountability, and continuous improvement. - Excellent communication and executive presence, able to operate at both the boardroom and front-line levels. Nice-to-Have Experience

Experience with offshore BPO teams or global sales teams, especially in high-velocity outbound environments. - Background in or close partnership with Revenue Operations, including CRM optimization, territory design, compensation planning, and sales tooling. - Familiarity with fintech, payments, logistics, or transportation industries. - Experience moving a business up-market (e.g., from SMB into Mid-Market/Enterprise) while preserving and scaling the existing core. - Prior leadership experience in high-growth startup or scale-up environments, where ambiguity is high and speed matters. If you are energized by building and scaling high-performance sales organizations, love combining systems thinking with hands-on leadership, and are excited by the opportunity to modernize payments in the transportation industry, we’d love to speak with you.