Mid-Market Account Executive

About Playground

Playground is building the operating system for child care. Our software helps child care providers manage billing, enrollment, parent communication, and more — so they can spend less time on admin work and more time with kids.

We’ve raised millions from top investors, secured statewide partnerships, and work with thousands of schools across the country.

We’re now expanding up-market — selling into larger multi-site operators, franchise systems, and state organizations — and we’re looking for an experienced Enterprise Account Executive to lead the charge.

The Role

Mid-Market sales at Playground has been mostly founder-led to date. Our team has successfully closed multi-site operators and large regional groups — proving strong product-market fit at the enterprise level.

Now, we’re ready to scale — and we’re looking for an Mid-Market AE who’s done this before.

This role is for someone who has already sold enterprise deals at an SMB-focused vertical SaaS (vSaaS) company — think companies like Toast, ServiceTitan, Mindbody, etc.

You know how to navigate longer, more complex sales cycles — but you’re still scrappy. You know what great looks like, but you’re excited to build the playbook alongside founders and help us win our next wave of enterprise customers.

What You’ll Do

• Own the full sales cycle from prospecting to close for enterprise accounts (multi-site operators, franchises, state organizations)

• Partner closely with Playground’s founders on sales strategy, late-stage deal support, and enterprise handoffs

• Navigate deals with multiple stakeholders — typically across operations, finance, and executive teams

• Build outbound pipeline into net-new markets — leveraging both existing relationships and self-sourced opportunities

• Run highly structured discovery and product demos — tying product value directly to customer pain

• Negotiate contracts, pricing, and terms with thoughtfulness and creativity

• Collaborate cross-functionally with Sales Development, Marketing, Product, and Customer Success teams to deliver exceptional customer outcomes

• Help shape our enterprise sales motion — including messaging, process, and playbooks

About You

• 4+ years of quota-carrying sales experience in B2B SaaS

• Mid-Market AE experience at an SMB-focused vSaaS company is required (Toast, ServiceTitan, Mindbody, etc.)

• Proven track record of closing new business with multi-month sales cycles and multiple stakeholders

• Strong outbound prospecting skills — you build your own pipeline

• Comfortable running discovery and demos with operational buyers and executives

• Thrives in a high-ownership, fast-growth environment — where playbooks are still being written

• Low-ego, collaborative, and deeply curious about your customer’s world

• Based in NYC or willing to work in-person with our team in Union Square

Compensation

• OTE for this position is $200,000 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 salary is a guideline, and the salary 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

• Collaborative and supportive work culture with a high level of autonomy and room for growth

How to Apply: 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.