[Hiring] Director of Customer Success - SMB @ParentSquare

Role Description

We’re looking for a Director, Customer Success – SMB to own the strategy and the outcomes for our largest customer segment: more than 6,000 small and single-site districts across the country. You’ll be the leader accountable for how we show up for these customers at scale.

You’ll own our 1:many customer success motion end to end — the digital-first engagement model, the programs and playbooks behind it, and the adoption and retention numbers it produces. You’ll lead and grow our SMB customer success team, shape the operating and coverage model for the segment, and represent SMB when we’re deciding where to invest.

This is where customer outcomes and operational efficiency go hand in hand. We want thousands more districts getting real value from ParentSquare, and we want to get there through a model built to scale. You’ll be the one who takes it there.

Most importantly, you’re someone who shares in our passion for improving the lives of students through communication.

• Own adoption, retention, and expansion outcomes for our SMB segment, and report on them to our executive team
• Set the strategy for our 1:many motion, which uses a mix of automated, digital, and live touchpoints across onboarding, adoption, renewal, and expansion
• Lead, hire, and develop our SMB customer success team, shaping the structure, coverage model, and career paths as the team and customer base grow
• Scale the operating model behind the segment: enrollment thresholds, coverage ratios, capacity planning, and the efficiency targets that support them
• Partner with our Marketing and Customer Education teams on workshops, community programming, and lifecycle campaigns that reach thousands of districts at once
• Work with Customer Success Operations to operationalize the journey through the data, signals, and automation our motion depends on
• Align with Sales, Marketing, and Product on identifying expansion signals across the segment and acting on them
• Measure the effectiveness of our SMB programs, and move your team’s effort toward what the data shows is working

Qualifications

• 8+ years in Customer Success or Account Management within SaaS, where you’ve owned retention and adoption outcomes directly
• 4+ years of people leadership, including developing managers or leading a multi-layer team
• Experience building or scaling a 1:many, digital-first customer success motion — automation, digital campaigns, webinars, office hours
• A high-volume segment you’ve owned outcomes for, and the operational rigor to run it: segmentation, coverage models, capacity planning
• Comfort using customer data and usage signals to decide where your team spends its time and where risk is building
• A strategic mindset paired with operational follow-through — you can design the system and make sure it actually runs
• Strong executive communication, and the ability to influence across Sales, Marketing, Product, and Operations

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
• 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.

Salary

The salary range for this role will be $110,000-$130,000, DOE.