Mid Market Customer Success Manager

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 to grow extremely fast. We recently raised millions of dollars, have several statewide contracts, and are working with thousands of schools across the country. Additionally, our founders were recently honored as Forbes 30 under 30.

We are a team of owners, who are not afraid to dive into large, complex projects. If you are excited by the prospect of helping build Playground’s account management organization and joining a collaborative, high-growth startup — please apply!

About the Role

Join Playground's Customer Experience team and own the relationship with our mid-market customers, multi-location operators running their businesses on our platform.

You'll manage a portfolio of these accounts end-to-end: building real relationships with operators, driving adoption across their locations, and making sure they're getting full value from Playground. The best version of this role is proactive - you know your customers well enough to spot risks and opportunities before they surface in a support ticket.

What You'll Do

• Build Strong Relationships: Develop deep, multi-threaded connections with mid-market clients to fully understand their needs, challenges, and goals.

• Reduce Churn & Boost Activation: Proactively implement strategies to minimize churn while driving increased activation and engagement across customer accounts.

• Build Process & Scale: Design repeatable playbooks, intervention frameworks, and customer journey touchpoints that the broader team can leverage.

• Collaborate Cross-Functionally: Partner with the Product team to provide customer feedback and champion innovative enhancements that deliver exceptional client value.

• Seize the Opportunity: Playground is a place where doers thrive. If you see a problem, solve it. If you see an opportunity, run with it!

How Our Mid Market Team works

Stay Ahead — We don't wait for problems to find us. You'll use data, product signals, and your own judgment to get in front of risks before they become churn conversations.
Raise the Bar — Good enough isn't the standard. You'll be expected to look at every playbook, every touchpoint, every conversation and ask how it could be better - then make it better.
Move as One — You won't operate in a silo. You'll work lockstep with onboarding, product, and support so your customers get a seamless experience. When one of your accounts needs something, the whole team is behind you.

This is an in-person role based in our Denver or NYC office.

• Minimum 2+ years of experience in a customer success, account management, or related role within a SaaS company, specifically serving mid-market or ENT clients.

• Proven track record of managing a book of business and owning customer retention.

• Experience in contract renewals and retention conversations.

• A builder’s mindset: you’ve helped stand up or improve CS processes, playbooks, or systems at a previous company.

• Excellent verbal and written communication and interpersonal skills.

• Strong problem-solving abilities and a proactive approach.

• Proficiency with CRM software and customer success tools.

• Adaptability and ability to work independently as part of a team in a fast-paced startup.

• Experience at a high-growth startup

• Experience with childcare management software

• Experience in early childcare

Salary for this position is $145,000 – $155,000 OTE 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.

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental benefits

• $1,200/year education stipend

• Free lunch daily

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

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 Lodo, Denver or 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.