Customer Success Manager, ParentSquare Pay

Who We’re Looking For: We are seeking a customer-centric, detailed-oriented Customer Success Manager, Payments to join our team supporting one of our newest products, ParentSquare Pay. In this role, you will act as the single, end-to-end owner for our ParentSquare Pay customers and accounts. You are both the technical expert who gets an account configured and onboarded, and the relationship owner who ensures that setup translates into active, sustained transacting usage. You won't hand the account off after go-live; you'll stay with your portfolio, proactively driving adoption, retention, and growth Most importantly, you’re someone who shares in our passion for improving the lives of students through communication. This role will include: End-to-End Onboarding & Integration: Manage new account setup from intake to activation. Set up Stripe/bank accounts, guide districts through government-entity verification (KYC), configure GL codes, payment roles/permissions, fee structures, and approval workflows. Portfolio & Relationship Management: Proactively own and manage the success of a portfolio of ParentSquare Pay accounts. Build relationships with key school and district finance decision-makers (e.g., bookkeepers, finance directors). Adoption Strategy & Activation: Own a defined post-setup adoption cadence (30/60/90-day check-ins) to monitor account-health data, remove blockers, and drive accounts to their first transaction and sustained usage. Training & Enablement: Run onboarding trainings, webinars, drop-in office hours, and best-practice sessions for district finance and office staff. Ongoing Support & Account Administration: Troubleshoot payment reporting, reconciliation, and payout timing questions. Re-onboard accounts after staff turnover and process account updates or escalations. Expansion & Retention: Identify opportunities to expand payment use cases within accounts (e.g., moving from seasonal events to district-wide adoption) and partner with CS/Sales on renewals. Cross-Functional Voice of Customer: Work closely with Product Management and Engineering to surface configuration friction, feature gaps, and feedback prioritized by usage impact. Our ideal candidate will have the following: 2+ years of relevant Customer Success, Account Management, or Implementation experience within a SaaS, Fintech, or software environment. Experience working with or supporting K-12 schools, districts, or EdTech platforms is strongly preferred. Comfort working inside technical/financial systems and confidence troubleshooting them methodically (experience with Stripe/Stripe Connect or payment gateways is a plus). Data-literate mindset with the ability to act on usage/account-health metrics to prioritize proactive outreach. Excellent communication, project management, and relationship-building skills with non-technical school staff. Extreme attention to detail—you are comfortable being the last line of defense on setups involving real money. The perks of working for us are great! You’ll get your foot in the door as our company continues to grow. We’re big believers in work-life balance and provide: Employer-paid health insurance (including dependent coverage) An employer-matched 401K retirement savings program from day 1 Paid Parental Leave Stock options Health + wellness reimbursements PTO that increases each year 15 paid holidays, including your birthday! As a fully remote team, we’ll make sure you have all the tools and equipment you need to make your home office a place where you can thrive. We're an equal opportunity employer. All applicants will be considered for employment without attention to age, race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status. We are committed to maintaining a drug-free workplace in compliance with applicable state laws. The total OTE for this role will be approximately $65,000 to $85,000, DOE.