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 a Sales Development Representative to generate and qualify leads.

The Role

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 all levels.

Now, we’re ready to scale — and we’re looking for an SDR who’s done this before.

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

You know how to prospect and qualify in complex environments — but you’re scrappy. You’re excited to build the playbook alongside founders and help us win our next wave of enterprise customers.

The purpose of this role is grow into SMB and Mid Market Account Executive roles at Playground.

What You’ll Do

Prospect and generate leads for enterprise accounts (multi-site operators, franchises, state organizations) via email, phone, and LinkedIn.

Qualify inbound and outbound leads through discovery calls.

Schedule demos and meetings for Account Executives.

Build and manage outbound pipeline into net-new markets.

Research prospects and tailor outreach to customer pain points.

Collaborate with Marketing, Sales, and founders on lead generation strategies.

Help shape our SDR processes, messaging, and playbooks.

About You

1+ years in SDR or lead generation role in B2B SaaS.

Experience at an SMB-focused vSaaS company required (Toast, ServiceTitan, Mindbody, etc.).

Proven track record of meeting lead quotas and qualifying opportunities.

Strong outbound prospecting skills — you build your own lists.

Comfortable with CRM tools like Salesforce.

Thrives in a high-ownership, fast-growth environment.

Low-ego, collaborative, and curious about customers.

Based in NYC or willing to work in-person in Union Square.

Compensation

OTE for this position is $90,000 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 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.