# Mid Market Customer Success Manager

**Company:** [Playground](https://hotfix.jobs/companies/playground)
**Location:** New York, NY
**Role:** Customer Success
**Salary:** $145k – $155k/yr
**Experience:** 2+ years
**Skills:** Customer Success, Account Management, SaaS, CRM, Customer Retention, Contract Renewals, Playbooks, Cross-Functional Collaboration, Problem-Solving, Communication
**Posted:** 2026-04-17

> Own relationships with mid-market childcare operators, driving adoption, reducing churn, and building scalable CS processes in a fast-paced SaaS startup.

## Job Description

## 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

## Similar roles

- [Account Manager 3, Customer Success](https://hotfix.jobs/jobs/f4b3957d-2896-45bf-a02c-0cadb747184f) - RSA - Remote - $140k – $160k/yr
- [Capture Engineer](https://hotfix.jobs/jobs/b821b369-5d5e-4c65-be05-872280e63bef) - Usul - San Francisco, CA - $140k – $200k/yr
- [Manager, Customer Success](https://hotfix.jobs/jobs/dffa9aa7-6068-4ad7-9b76-1cdb485c1468) - Permitflow - New York, NY - $150k – $190k/yr
- [Deployment Strategist](https://hotfix.jobs/jobs/260f3f25-59c5-4171-92de-3a8518783110) - Usul - San Francisco, CA - $140k – $200k/yr
- [AI Customer Success Manager](https://hotfix.jobs/jobs/7c75edbc-813a-4f15-b523-0ad3a9aff5f3) - Raylu - New York, NY - $140k – $190k/yr

**Apply:** https://hotfix.jobs/jobs/ad097849-c542-46c2-ada0-be6ac45ffda7
**Canonical:** https://hotfix.jobs/jobs/ad097849-c542-46c2-ada0-be6ac45ffda7