Mid Market Customer Success Manager

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.

What You Need

• 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

Compensation

• Salary for this position is $145,000 – $155,000 OTE subject to standard withholding and applicable taxes.
• Competitive salary + equity
• 3 weeks of PTO
• Health, vision, and dental benefits
• $1,200/year education stipend
• Free lunch daily