SDR (Sales Development Representative)

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 cu