Mid Market Customer Success Manager
About The Position
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.
Requirements
- 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.
Nice To Haves
- Experience at a high-growth startup
- Experience with childcare management software
- Experience in early childcare
Responsibilities
- 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!
Benefits
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
Number of Employees
1-10 employees
