Role

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.

Key responsibilities:
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.