Head of Sales, SMB

The role

This leader will build and execute a cohesive revenue strategy spanning outbound motions, mid-market, and account management. You will manage a team of 6 managers and 55 individual contributors to drive acquisition, expansion, and retention.

What you will do

• Develop and own the integrated revenue strategy across acquisition, activation, expansion, and retention
• Set goals, metrics, and leading indicators for the revenue funnel
• Build and maintain a disciplined forecasting and pipeline management process
• Scale and optimize the phone-based, outbound sales engine
• Implement and refine playbooks, scripts, and cadences
• Build and execute a strategy to move up-market to larger fleets
• Recruit, hire, and ramp 20+ Account Executives in the next 6 months
• Design and refine expansion and cross-sell motions
• Build out a robust Account Management function
• Lead, mentor, and develop a team of 6 sales leaders and 55+ ICs

Required qualifications

• 10+ years of experience in B2B sales
• 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 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
• Deep comfort with data and metrics
• Demonstrated ability to recruit, develop, and retain high-performing talent

Nice to have

• Experience with offshore BPO teams or global sales teams
• Background in or close partnership with Revenue Operations
• Familiarity with fintech, payments, logistics, or transportation industries
• Experience moving a business up-market while preserving and scaling the existing core
• Prior leadership experience in high-growth startup or scale-up environments

About the company

AtoB is building Stripe for Transportation to modernize the payments infrastructure for trucking and logistics. The company has raised $125 million+ from various investors and was named to the Forbes annual Next Billion-Dollar Startup List.