Head of Sales, SMB

This leader will be responsible for building and executing a cohesive revenue strategy that spans our high-velocity outbound motions, mid-market and emerging upmarket plays, and our growing account management and expansion engine. Today, approximately 80% of new business is generated via high-volume outbound outreach to SMB and Mid-Market customers, primarily in a phone-based, inside sales environment. As such, the ideal candidate has a proven track record leading large, outbound-centric sales organizations where success is driven by activity, quality of conversations, and disciplined execution.

You will directly manage a team of 6 managers and 55 individual contributors, spanning both full-time employees and offshore BPO team members. Experience partnering with and scaling offshore BPO teams is a strong plus.

A core mandate for this role is to successfully move AtoB up-market while continuing to scale our existing high-velocity engine. This includes hiring and ramping 20+ new Account Executives over the next 6 months, evolving our go-to-market coverage model, and ensuring we have the systems, processes, and culture in place to support sustained growth.

Beyond new business, you will refine and scale our expansion and cross-sell motions and build out a more robust Account Management function focused on multi-product adoption, customer outcomes, and long-term retention.

This is a highly strategic, hands‑on role for a strong systems thinker who understands how people, process, and technology intersect to create predictable, efficient revenue. Experience in or close partnership with Revenue Operations is a significant plus.

1. Own the Revenue Engine: Acquisition, Activation, Expansion, Retention

• Develop and own the integrated revenue strategy across new logo acquisition, activation of new customers, expansion / cross-sell, and retention.

• Set clear goals, metrics, and leading indicators for each pillar of the revenue funnel (e.g., outreach activity, conversion rates, activation milestones, expansion revenue, NRR/GRR).

• Build and maintain a disciplined forecasting and pipeline management process that drives predictability and accountability.

2. Lead High‑Velocity Outbound Sales to 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.