SDR (Sales Development Representative) - NYC

Playground • New York, NY

97d

About The Position

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. 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.

Requirements

• 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.

Responsibilities

• 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Number of Employees: 11-50 employees