← All roles

Head of Sales, SMB

AtoB· Sales
Apply on company site
Hybrid (San Francisco Bay Area), Hybrid (New York Metropolitan Area), Hybrid (Toronto)Full-timePosted 6mo ago

About the role

Senior sales leader responsible for building and executing a cohesive revenue strategy across outbound SMB, mid-market, and account management; scale high-velocity outbound, move up-market, and expand multi-product adoption while partnering with Revenue Operations and cross-functional teams.

Responsibilities

  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.

Qualifications

  • 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.

Skills

Required:Revenue strategyForecasting & pipeline managementOutbound sales leadershipHiring & ramping large teamsCross-functional collaborationSystems thinkingData-driven decision making

Benefits

  • Apply for this Job (link in description)
Last updated Jul 29, 2026. Interested? Apply on the company site.
AtoB logo

About AtoB

Rebuilding global transportation payments.

The trucking and logistics industry provides the backbone of the economy, but the payments infrastructure on which it runs is broken; the existing suite of payment tools is outdated, difficult to use, prone to fraud, and saddled with hidden fee structures. AtoB is building Stripe for Transportation — modernizing the payments infrastructure for trucking and logistics, where capital movement occurs quickly and transparently. Our flagship product is the AtoB Fuel Card, a zero-fee fuel card accepted anywhere built for fleets of all shapes and sizes.

fintechsaaspaymentssupply-chaintransportation
Company profileWebsite

More open roles at AtoB