Founding Customer Success Manager
Quick Summary
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,
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).
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.
Responsibilities
~1 min read- →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
- 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+)
- Excellent written and verbal communication in English
- 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
Listing Details
- Posted
- February 28, 2026
- First seen
- March 26, 2026
- Last seen
- April 16, 2026
Posting Health
- Days active
- 21
- Repost count
- 0
- Trust Level
- 23%
- Scored at
- April 16, 2026
Signal breakdown
Please let Applytochalkbooks know you found this job on Jobera.
1 other job at Applytochalkbooks
View all →Explore open roles at Applytochalkbooks.
Similar Founding Customer Success Manager jobs
Stay ahead of the market
Get the latest job openings, salary trends, and hiring insights delivered to your inbox every week.
No spam. Unsubscribe at any time.