Head of Customer Success

About the Role:

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.

You’ll own the operational relationship with the fleet managers, maintenance leads, dispatchers and drivers who use ServiceUp every day. Each account has a Sales and CS pair: Sales signs and grows the contract, and you make sure the customer gets the value we promised. This is a player-coach build initially. You’ll move ServiceUp to a scalable CS function driven by data, owning key accounts yourself while you hire and lead the team.

What You'll Do:

• 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.

What You'll Bring:

• 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.

Why You’ll Love Working Here:

We live our values every day: Team First, Work Smart, Own It, Be Bold, Push Boundaries. If that sounds like you, you’ll fit right in

What We Offer:

• 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

Benefits may vary by location and role.

If you’re motivated by impact and aligned with our values, we want to hear from you. You don’t need to meet every single requirement — we care about your skills, drive, and how you work with a team.

Service Up is an equal opportunity employer committed to a diverse, inclusive workplace where everyone can do their best work.