Sales Manager

About Playground

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 providing incredible child 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 work of running a center.

Playground is at an inflection point and poised for rapid growth. We recently raised millions of dollars, secured several statewide contracts, and are working with thousands of schools across the country. Our founders were recently honored as Forbes 30 Under 30.

We are a team of owners, unafraid to dive into large, complex projects. If you’re excited about helping build Playground’s sales organization and joining a collaborative, high-growth startup, we want to hear from you!

What You’ll Do

• Manage and coach a team of Account Executives & Sales Development Representatives
• Improve rep performance through call reviews, live coaching, and structured feedback
• Optimize the sales funnel, improving demo-to-close conversion and time to close
• Partner with RevOps to forecast accurately, track KPIs, and drive pipeline visibility
• Collaborate with Marketing to ensure tight lead handoffs and iterate on what makes a high-quality lead
• Collaborate with Customer Success to ensure customers are properly sold and handed off well
• Refine sales processes across discovery, qualification, objection handling, and competitive differentiation
• Support hiring, onboarding, and scaling of the sales team as we grow—including joining sales calls to model best practices and stay close to the pitch
  
  

What Makes a Great Fit

• 2–5 years of experience managing high-performing sales teams in a B2B SaaS environment
• Must have sold software to SMBs in a vertical SaaS (vSaaS) context
• Deep understanding of SMB buyer psychology and how to run a consultative sale with time-constrained, cost-conscious decision-makers
• Track record of success with inbound sales motions, and comfort coaching early outbound reps
• Proficient in Salesforce for pipeline management and optimization
• Excited to roll up sleeves to help build and scale systems, playbooks, and processes
• Excellent communicator, motivator, and coach who leads by example
• Metrics-driven and confident owning weekly forecasting and team performance
  
  

Why Join Playground

• Competitive salary + equity
• 3 weeks of PTO
• Health, vision, and dental benefits
• $1200/year education stipend
• Free lunch daily
• New MacBook and any equipment you need
• Collaborative and supportive work culture with a high level of autonomy and room for growth
• Help accelerate our mission to make excellent child care accessible to all!
  
  

Compensation

The annual OTE (60/40 split) for this position is $135,000 - $155,000, subject to standard withholding and applicable taxes. Job level and actual compensation will depend on individual qualifications assessed during the interview process (skills, prior experience, potential impact, scope of role, and work location). The listed range is a guideline and may be modified.

What Makes a Great Fit

If you’re a hustler who’s excited to join a mission-driven, early-stage company with ownership, craftsmanship, and empathy at the center of what we do, apply now.

The Playground Team is fully in-office in Union Square, NYC. Please make sure you are open to a fully in-person role before applying.

Check out: https://www.tryplayground.com/about to learn more about our journey and co-founders Dan, Josh, and Sasha.

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 providing incredible child 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 work of running a center.