VP of SMB Sales

Playground is working to make excellent child care accessible to all. Playground has built best-in-class software to manage all aspects of running a child care business. We believe that providers should focus on delivering incredible care — the kind of work that only people can do — and that software should manage the rest. We’re building the child care management platform that eliminates the administrative burden of operating a center.

Playground is at an inflection point — and poised to grow extremely fast. We’ve recently raised millions in funding, secured several statewide contracts, and are working with thousands of schools across the country. Additionally, our founders were recently honored as Forbes 30 Under 30.

We are a team of owners who are not afraid to dive into large, complex challenges. If you’re excited by the opportunity to scale a high-performing sales organization at a mission-driven, high-growth startup — we’d love to meet you.

Playground is hiring a VP of SMB Sales to own revenue delivery and go-to-market strategy for our SMB segment — including single-location centers, small multi-site operators, and family childcare providers across the country.

This is our largest and fastest-growing segment, and the foundation is working. Your role is to scale it — without breaking what makes it successful.

You’ll operate across three core areas: leading the business, developing your people, and building the systems that allow us to scale. You’ll oversee Regional Directors and SDR leadership, ensuring strong pipeline generation, disciplined execution, and consistent performance across the funnel.

This is a pure leadership role — your success is measured by your team’s success. You’ll report directly to the Head of Sales and act as a key partner on org design, territory planning, pricing strategy, and overall GTM execution.

• 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

• Drive predictable, repeatable revenue through strong pipeline management and stage discipline

• Oversee SDR performance across inbound and outbound, ensuring strong pipeline coverage and conversion

• 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

• Design onboarding programs that ramp AEs quickly in a high-velocity sales environment

• Set and maintain a high talent bar across all levels of the team

• Build clear career pathways from SDR to AE to support long-term talent development

• Reinforce a discovery-first, outcome-driven sales methodology across the team

• Ensure reps run high-quality discovery calls with clear pain identification and outcome mapping

• Elevate demo quality to align with buyer needs and clearly communicate value

• Maintain strong competitive positioning through value-based selling

• Partner with leadership on territory design, quotas, compensation plans, and capacity planning

• Collaborate with Marketing, Product, and Customer Success to improve GTM alignment

• Own Salesforce data integrity, pipeline hygiene, and forecasting accuracy

• Build and refine the SMB sales playbook including talk tracks, objection handling, and ROI frameworks

• Drive adoption of Playground’s integrated payments offering

• Partner with Finance and Payments teams to optimize pricing, margins, and positioning

• Increase payment attach rates as a key revenue lever alongside SaaS

• 10+ years of B2B SaaS sales experience, with 6+ years in sales leadership (Director level or above)

• Proven experience scaling SMB sales teams (e.g., growing from ~5 to 20+ AEs)

• Deep experience in high-velocity, transactional sales environments (2–6 week sales cycles)

• Experience with fintech or payments-integrated business models

• Strong Salesforce and data-driven management skills

• Experience designing comp plans, territories, and capacity models

• You’ve built scalable sales infrastructure including onboarding, playbooks, and coaching systems

• You think in systems and can diagnose performance issues across people, process, pipeline, and product

• You are passionate about discovery-driven selling and coach it consistently

• You lead through leverage — developing leaders and elevating entire teams

• You bring strong opinions but remain adaptable in a fast-changing environment

• Experience in vertical SaaS or high-growth startup environments is a strong plus

• High emotional intelligence and ability to build trust quickly

• Low ego, high accountability mindset

• Strong coaching orientation — you develop people rather than step in for them

• Curious and analytical in how you approach problems

• Bias for action with the ability to move quickly and iterate

• Competitive salary + meaningful equity

• 3 weeks PTO

• Health, vision, and dental benefits

• $1,200/year education stipend

• Free lunch daily

• A strong sales culture with defined methodology and a robust playbook

• High-growth environment with significant opportunity for impact and advancement

On-target earnings for this role are $400,000, including base salary and variable compensation. Final compensation will be determined based on experience, impact, and scope.