Head of Marketing

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 solving high-impact problems across a growing startup and want to work closely with company leadership to build operational excellence from the inside out, we want to hear from you!

The Role

We’re looking for a Head of Marketing to own our full-funnel demand generation strategy and build the systems that drive predictable, high-quality pipeline. From outbound to paid, SEO to lifecycle—you’ll lead campaigns that convert, scale, and power our GTM motion. We’ve laid strong early foundations. Now, we’re looking for an experienced and strategic marketer to take ownership of the engine and scale it with urgency and care.

The ideal candidate has deep expertise in SMB demand generation, thrives in data-driven environments, and understands how to orchestrate high-impact campaigns that seamlessly integrate sales and marketing efforts. This leader will drive end-to-end demand generation campaigns, from strategy to execution and measurement. You will be expected to work cross functionally to scale acquisition efforts between the Marketing and Sales team and can easily switch gears between goal setting, executing, and driving cross-functional buy-in.

This is a dream role for a creative, analytical growth marketer who wants full ownership of the engine—and the ability to build it right. If you’re someone who thrives at early-stage companies, loves launching new plays, and wants a seat at the leadership table, this role offers high impact, high visibility, and room to scale. You’ll have autonomy, smart collaborators, and the mandate to make bold moves—whether that’s launching new channels, refining attribution, or leading high-performing campaigns across the funnel.

What You’ll Do

• Own and scale demand generation across outbound, paid, SEO, and lifecycle.

• Launch creative, data-driven campaigns that generate pipeline.

• Build performance tracking, attribution, and experimentation systems that unlock new growth loops.

What You Bring

• 5–10+ years in B2B growth marketing (Series A–C preferred) with deep ownership of demand gen.

• Proven success in SMB marketing; strong intuition for small business buying behavior.

• Fluency in AI-driven personalization, buyer intent data, and marketing automation.

• Strong technical chops across attribution, analytics, and campaign ops.

• A performance-obsessed, highly analytical mindset with sharp instincts for iteration.

• Up-to-date with the latest trends and best practices in online marketing and measurement.

• You are comfortable working in a scaling startup environment and adapt quickly.

• You value collaboration and thrive in ambiguity.

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.

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 child care accessible to all!

Compensation

Salary for this position is $175,000–$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 range is a guideline, and the range for this role may be modified. Job level and actual compensation will be based on skills, experience, and interview performance.