Head of Sales
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 account management organization and joining a collaborative, high-growth startup, we want to hear from you!
About the Role
As our Head of Sales, you will own the end-to-end sales strategy, execution, and team building. This is a hands-on leadership role where you’ll not only define the vision for our sales organization but also roll up your sleeves to ensure consistent execution and results. The ideal candidate will bring a strong background in B2B SaaS sales (experience in vSaaS is a huge plus) and a proven track record of scaling teams and driving revenue growth in SMB markets.
Key Responsibilities
• Sales Strategy & Leadership: Develop and execute a sales strategy that aligns with company goals, focusing on driving growth in SMB markets.
• Team Building & Management: Recruit, train, and lead a high-performing sales team, fostering a culture of accountability, collaboration, and continuous improvement.
• Pipeline Management: Oversee the sales pipeline, ensuring a healthy mix of leads, opportunities, and conversions.
• Data-Driven Decisions: Set clear KPIs, analyze performance metrics, and use insights to refine strategies and improve outcomes.
• Customer-Centric Approach: Partner with marketing and customer success teams to ensure a seamless customer experience from lead generation through onboarding.
• Revenue Accountability: Own revenue targets and forecast accurately to support financial planning and investor communications.
What We’re Looking For
• 8+ years of experience in B2B SaaS sales, with at least 3 years in a senior leadership role.
• Proven success scaling sales teams and building processes in a high-growth environment.
• Experience selling to SMBs is required; familiarity with vertical SaaS (vSaaS) is strongly preferred.
• Expertise in using modern sales tools and CRM systems to track performance and optimize workflows.
• Exceptional communication, negotiation, and presentation skills.
• A hands-on leader with a collaborative mindset and the ability to inspire teams.
• Passion for working in a fast-paced, high-growth environment with ambitious goals.
Compensation
The annual salary range for this position is $150,000 - $300,000 subject to standard withholding and applicable taxes.
Job level and actual compensation will be decided on factors including, but not limited to, individual qualifications objectively assessed during the interview process (including skills and prior relevant experience, potential impact, and scope of role), market demands, and specific work location. The listed range is a guideline, and the range for this role may be modified.
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 childcare accessible to all!
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.
If you want to learn more about what life at Playground HQ is like, check out this post about one of our past recruiting happy hours + our Polaroid wall (our favorite office tradition)!
Average salary estimate
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Join Playground, a trailblazer in child care management software, as the Head of Sales and help us make excellent child care accessible to all! Based in the vibrant heart of New York City, you will be at the helm of our sales strategy, driving growth within the SMB market. With over 8 years of experience in B2B SaaS sales and a knack for orchestrating team dynamics, you'll lead our sales team while fostering a culture of accountability and collaboration. Dive into this hands-on role where you’ll not only envision our sales organization’s future but also actively engage in the execution of strategies. You will oversee the sales pipeline, utilizing data-driven insights to refine approaches for maximum impact. Your leadership will ensure we meet revenue targets and create exceptional customer experiences alongside our marketing and customer success teams. Enjoy flexible perks like competitive salary, equity, health benefits, and generous PTO while being part of a mission-driven company that values craftsmanship, ownership, and empathy. If you're passionate about driving growth and eager to take on big challenges, we can't wait to meet you!
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