Founding Customer Success Manager

ChalkBooks is on a mission to empower millions of students with better educational opportunities and enable tens of thousands of independent schools to become financially sustainable.

Independent schools heavily rely on fundraising to run themselves, raising billions for student scholarships and hundreds of billions for new buildings and remodeling. As a multi-billion dollar opportunity with too many legacy offerings solving too few needs, there has never been a better time to build for school fundraising.

ChalkBooks is an AI-powered fundraising results acceleration platform. We have developed a best-in-class AI-powered school fundraising CRM, fundraising communication, donor management, task management, and purpose-built embedded fin tech workflows.

Problems We Are Solving

Fundraising in independent schools is especially difficult because independent school fundraising teams are often under‑resourced and get distracted daily from outbound fundraising activities with school admin tasks (e.g., substituting a class or helping with pick up and drop off).

Fundraising teams in independent schools are already thinly stretched and have to find time to meet ever‑growing fundraising goals. With pressure from the Head of School and the CFO, the Director of Advancement and her team must bring anywhere from 10% to 25% of an average school’s annual budget and over 90%+ for capital projects. However, due to the plethora of disconnected tools and analog processes, they lack the basic context to build meaningful relationships, and closing larger gifts takes longer. Personalization of communication, a cornerstone of fundraising, takes, on average, 30‑40 minutes per email (a whopping 10‑15 hours per week).

Intensifying competition for donors’ attention will push school fundraising teams to adopt new technology to stay competitive, and ChalkBooks will lead the way.

Job Description

We are seeking a highly skilled and motivated Founding Customer Success Manager to play a pivotal role in shaping our customer success strategy and ensuring our clients exceed their fundraising goals.

As a critical member of our Customer Experience team, you will have the unique opportunity to work directly with the CEO to help scale ChalkBooks to new heights.

We are a fast‑paced, early‑stage startup looking for team members who thrive in ambiguity, are excited to play a big role in proving our customer success playbook, and will enthusiastically onboard and manage their book of customer accounts with minimum supervision.

Responsibilities

• Own the entire post‑sales process from the initial onboarding to continued support for up to 100+ customer accounts
• Develop and execute comprehensive customer success plans, including onboarding, training, and ongoing support
• Monitor customer health metrics and product usage to proactively address potential issues
• Conduct regular business reviews and feedback sessions with customers to ensure alignment with their goals
• Collaborate with product and engineering teams to relay customer feedback and influence product development
• Identify opportunities for upselling and cross‑selling to drive additional value for customers

Success Metrics

• Achieve an average onboarding rating of 9/10 for each onboarding
• Achieving 100% success rate on new customer deployments

Requirements

• 5+ years of SaaS customer success experience in early‑stage startups (Seed+)
• Skilled at communicating at multiple levels of a school
• Highly empathetic and patient
• Proven track record of managing customer relationships and driving customer satisfaction at early stage companies
• Strong analytical skills with the ability to leverage data to drive decisions
• Ability to anticipate customer needs and proactively address them
• Well‑versed in project management and AI tools to drive productivity
• Excited to be a key contributor to building the customer success playbook that will take us to $100M+ in ARR

Bonus Points

• Passion for improving educational outcomes for K-12 students
• Highly motivated and focused, familiar with Extreme Ownership
• Prior experience working in private schools