Head of Customer Success

The Role

Player-coach. You own a direct book of accounts (60%) and lead a small, growing team of Customer Success Managers (40%). You run onboarding on your own accounts so you stay close to how the product works in practice, then build the system and playbooks around what you learn. This is not a role where leadership means distance from the customer.

What You Own

• Team leadership: goal-setting, 1:1s, performance management, escalation protocols, and CS framework development
• Direct accounts: full lifecycle ownership from onboarding through renewal — you are the primary point of contact for your book
• Onboarding: run onboarding virtually and onsite for your accounts; standardize the process for the broader team
• KPIs: net revenue by customer, churn rate, net patients per account, clinical quality adherence — reported weekly to the CCO
• Cross-functional: primary voice of the customer to Product and Operations; translate usage patterns into roadmap inputs

What We Are Looking For

• 5 years in SaaS customer success with direct account ownership and measurable retention and expansion outcomes
• 2 years building or leading a CS team in a scaling environment, including performance management and process development
• Data-driven by default: you pull your own reports, build dashboards, and let usage data drive your weekly priorities
• Track record building CS infrastructure: onboarding playbooks, health scoring models, lifecycle workflows
• Strong cross-functional communication at both the operational and executive level
• Software background required. Healthcare experience a plus

Why This Role

You will define what customer success looks like at Truentity for the next several years. Direct line to the CCO, ground-level data from accounts you personally own, and a genuine problem worth solving: 65 million Americans Medicare beneficiaries with chronic conditions, and a platform built to meet them at the closest healthcare touchpoint they already trust.

About the Company

Truentity Health is the operating system for pharmacy-based clinical care. We give independent pharmacies the technology to deliver chronic care management and remote patient monitoring at scale — closing care gaps at the most accessible healthcare touchpoint patients already use.

Apply: join hcs@truentity.com — include your resume and a brief note on a CS framework or retention initiative you built.

Pay: From $125,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Application Question(s):

• Describe a CS framework or process you built from scratch; onboarding, health scoring, lifecycle playbook, or similar. What did you build, what problem did it solve, and how did you measure whether it worked?
• Walk me through how you use data day-to-day to manage your accounts. What does your weekly review look like, and give me an example where the data told you to do something you would not have done otherwise.
• You have a direct book of accounts and a team to develop simultaneously. Tell me about a time you had to hold both at once — what broke down, what did you deprioritize, and what would you do differently?
• Describe a time you managed an account where you had more than one decision-maker or stakeholder with competing priorities. Who were the stakeholders, what did they each want, and how did you hold the relationship together without losing the account?

Work Location: In person

Salary : $125,000