[Hiring] Manager, CSM @ParentSquare

Role Description

As the Manager of Customer Success for our SMB segment, you will own the strategy and execution for over 6,000 districts nationwide. This is a high-impact leadership role focused on building a world-class "1:many" digital-first engagement model. You will design the playbooks that ensure our smallest customers receive the right touchpoints at the right time to drive massive adoption, retention, and expansion. You’ll lead a dedicated team of SMB CSMs, balancing automated workflows with high-value human intervention to scale ParentSquare’s footprint in the SMB market.

• Architect the Scaled Journey:
  • Design and refine a digital-first customer journey that blends automated triggers, live workshops, and community-led programming.
• Drive Growth Metrics:
  • Take full accountability for retention, health scores, and expansion revenue across the SMB portfolio.
• Lead & Coach:
  • Manage a team of four CSMs, coaching them to execute at scale while maintaining a high standard for customer outcomes.
• Operationalize Success:
  • Partner with CS Ops and Marketing to build repeatable playbooks and automated touchpoints that identify risk early and surface expansion signals.
• Data-Driven Iteration:
  • Use product usage and engagement data to continuously "A/B test" our success motions and improve efficiency.
• Cross-Functional Influence:
  • Collaborate with Product and Sales to ensure the SMB voice is heard and that our digital-first motions align with the overall company roadmap.

Qualifications

• 3+ years of experience in Customer Success or Account Management within a SaaS environment, preferably with direct SMB experience.
• 2+ years of people leadership experience, with a track record of coaching and developing high-performing CSMs.
• Proven success managing or designing programs for a high-volume book of business while consistently driving customer health and retention metrics.
• Experience building and executing 1:many engagement strategies, including automation, digital campaigns, webinars, and office hours.
• Strong understanding of customer journey mapping and lifecycle management.
• Comfort using customer data and usage signals to prioritize outreach and proactively manage risk.
• A strategic mindset balanced with operational rigor, you can design the system and ensure it runs.
• Exceptional cross-functional collaboration skills and the ability to influence across teams.
• Most importantly, you’re someone who shares in our passion for improving the lives of students through communication.

Benefits

• 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.
• 16 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.