VP of SMB Sales

About the Company

Playground is working to make excellent child care accessible to all. We have built best-in-class software to manage all aspects of running a child care business, aiming to eliminate the administrative burden of operating a center.

Responsibilities

• Own the SMB bookings number, including new ARR, pipeline generation, and forecast accuracy
• Run a rigorous operating cadence including weekly forecasts, pipeline reviews, and deal inspections
• Hire, develop, and retain Regional Directors and support them in building high-performing AE teams
• Create a coaching-first culture grounded in call reviews, deal strategy, and continuous development
• Partner with leadership on territory design, quotas, compensation plans, and capacity planning
• Drive adoption of Playground’s integrated payments offering

Requirements

• 10+ years of B2B SaaS sales experience
• 6+ years in sales leadership (Director level or above)
• Proven experience scaling SMB sales teams
• Deep experience in high-velocity, transactional sales environments
• Experience with fintech or payments-integrated business models
• Strong Salesforce and data-driven management skills
• Experience designing comp plans, territories, and capacity models

Benefits

• Competitive salary + meaningful equity
• 3 weeks PTO
• Health, vision, and dental benefits
• $1,200/year education stipend
• Free lunch daily