Head of Customer Success

ServiceUp is reimagining a $200B+ industry with AI-powered orchestration for fleet and insurance vehicle repair. We’re the all-in-one platform bringing modern efficiency to a complex market. We’re trusted by some of the world’s largest and most sophisticated fleets and insurers.

ServiceUp is building its Customer Success function, and we’re hiring the leader to build it. You’ll own everything after the contract is signed: getting customers live, getting their vehicles and people onto the platform, and keeping them there. Our revenue is driven by usage, so every repair order (RO) a customer routes through ServiceUp is a direct measure of whether they’re getting value, and of whether the CS team is succeeding.

• →Own onboarding from signed contract to steady-state usage, with clear milestones and targets for time to first RO and time to value.
• →Run a structured Sales-to-CS handoff and coordinate launch work across data load, user setup, approval rules, shop coverage and integrations (fleet systems, telematics, ERP).
• →Define what “adopted” means for each segment, find the gaps between contracted scope and actual usage, and close them with Operations and the shop network team.
• →Run operational business reviews that show customers their value in their own numbers: cycle time, cost per repair, downtime and savings.
• →Design and build the account health model, including scoring, leading indicators and the playbooks each risk level triggers, and run save plans for at-risk accounts.
• →Lead the monthly cross-functional churn review and turn churn causes into a ranked list of product and operational fixes.
• →Hire and lead a team of Customer Success Managers (CSMs), set the coverage model by segment, and build the CS operating system in our CRM.
• →Report monthly to the CRO and leadership on retention, utilization, time to value and account health.

• 7+ years in Customer Success at a B2B SaaS company. Ideally you have built a CS function from zero or near-zero, including health scoring, playbooks, segmentation, coverage models and CRM setup.
• A record of improving retention and adoption that you can show in numbers.
• Experience in a usage-based or transaction-based revenue model.
• Willingness to initially be a player-coach who personally owns onboarding and key accounts while building the team.
• Comfort with data: you can pull usage data, spot slipping accounts and walk a fleet manager through their own numbers.
• Hands-on use of AI tools to cut manual CS work and extend how many accounts each CSM can cover.
• Strong project management across multi-site implementations with many stakeholders.