ParentSquare is a rapidly growing Santa Barbara-based company that’s changing the way schools and parents communicate every day. Sound simple? We strive to keep it that way! Our mission is to give schools the power to incredibly enhance family engagement for all students. ParentSquare and RemindHub, our flagship products, serve over 22 million students and drive our mission by providing unified communications tools -forms, sign ups, payments, RSVPs, direct messaging, language translations, chat and more. Remind Chat, our free product, reaches over 80% of K-12 students, providing a safe and easy-to-use platform for direct communication between teachers and families. And our latest innovation, SmartSites, offers state-of-the-art websites for school districts, enhancing their online presence and accessibility. 

We are not just creating a product; we are creating empowered educators and engaged parents to improve the lives of all students.  We are passionate advocates for our  customers and for our employees and we invite you to join us on this exciting journey.

Who we’re looking for:

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.

What You'll Do:

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.

Our ideal candidate will have the following:

• 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. 

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
• 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. 

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.