Role Overview
As the Head of Customer Success, you will own the operational relationship with fleet managers, maintenance leads, dispatchers, and drivers who use ServiceUp every day. You will be responsible for onboarding customers, ensuring they get the value promised, and driving customer success through data-driven decisions.
What You Will Do
You will own onboarding from signed contract to steady-state usage, run a structured Sales-to-CS handoff, and coordinate launch work across data load, user setup, approval rules, shop coverage, and integrations. You will also define what ‘adopted’ means for each segment, find gaps between contracted scope and actual usage, and close them with Operations and the shop network team.
Why It Might Be a Fit
You will be a player-coach who personally owns onboarding and key accounts while building the team. You will need to have a record of improving retention and adoption, experience in a usage-based or transaction-based revenue model, and comfort with data. You will also need to be willing to use AI tools to cut manual CS work and extend how many accounts each CSM can cover.
Requirements
- 7+ years in Customer Success at a B2B SaaS company
- Experience in building a CS function from zero or near-zero
- A record of improving retention and adoption
- Experience in a usage-based or transaction-based revenue model
- Comfort with data and AI tools
- Strong project management skills
Benefits
- Competitive pay with equity
- Medical, dental, and vision coverage
- Flexible PTO and company holidays
- Remote-friendly setup with home office support
- Learning and development budget
- Wellness stipend to support your health and well-being
- Paid parental leave
To apply for this job please visit ats.rippling.com.

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