Head of Customer Success

Head of Customer Success

About the Role

Goal for this Role

We’re hiring a Head of Customer Success to manage our existing portfolio of Truemed brand partners. Our brand partners are the heart of our business. Truemed’s Customer Success Team is responsible for managing our largest and most strategic relationships, such as Sleep Number, Peloton and Life Time Fitness. In this manager role you’ll be responsible for a high-performing team of Customer Success Managers and Directors. You’ll lead and coach the team, helping them deliver on ambitious targets, as well as roll up your sleeves to work directly with executives at existing Truemed customers in both the Enterprise and Mid-Market. You will be accountable for key metrics such as time to value, retention, and penetration rates.

We are looking for a self-starter who has demonstrated success dealing with ambiguity, operating in a high-growth environment, and solving complicated problems with limited oversight. Ideal candidates will have management and leadership experience scaling a technology sales team, superior communication skills, and a knack for understanding unique customer needs.

Outcomes for this Role

1. Drive Retention and Expansion Across Key Accounts

Ensure Truemed’s largest and most strategic brand partners — including enterprise relationships like Sleep Number, Peloton, and Life Time Fitness — achieve measurable success and renew at a high rate. This includes increasing partner engagement and penetration, expanding use cases, and identifying upsell and cross-sell opportunities that grow account value over time.

2. Build and Scale a High-Performing Customer Success Organization

Hire, develop, and lead a team of exceptional Customer Success Managers capable of managing complex enterprise relationships. Implement processes, playbooks, and success metrics that enable consistent delivery, proactive account management, and scalable partner support.

3. Strengthen Executive-Level Relationships and Operational Alignment

Serve as a trusted partner to C-level and senior stakeholders within key brand accounts while fostering tight internal collaboration between Sales, Product, and Marketing. Translate customer feedback into actionable insights that drive product innovation, integration improvements, and joint go-to-market initiatives.

4. Inform Executive and Product Teams on Market Trends and Customer Needs

Act as the voice of the customer to Truemed’s leadership and product teams. Surface emerging market demands, partner feedback, and competitive insights to shape product strategy, integrations, and future GTM initiatives.

5. Build a Proactive and Data-Driven Customer Success Function

Leverage analytics and tooling to create visibility into customer health, adoption, and ROI while automating repeatable workflows to improve efficiency and scalability. Use systems like CRM, CS platforms, and data dashboards to enable proactive engagement and measurable outcomes for customers.

Responsibilities

• Recruit, train, and lead a team of Customer Success Managers and Directors across the entire Truemed customer portfolio

• Help drive an engagement model focused on high growth accounts

• Develop and implement repeatable data-driven strategies to increase penetration across key brand partners, uncovering insights and levers that drive sustained adoption and growth

• Develop both the long-term vision and strategy for the team and drive progress toward key metrics

• Be accountable for increasing revenue, managing day-to-day operations, and scaling the team

• Coach, mentor, and guide the team in developing consultative and solution-based customer success and sales skills

• Effectively work cross-functionally across the organization to shape Truemed’s solutions to meet client needs

• Report on team performance and forecast, and channel customer insights into product roadmaps

What You Bring

• 7-10 years of technology sales, eCommerce or account management experience with 4+ years of progressive people management experience

• Experience leading Enterprise sales, account management and operations in an early stage, high-growth technology environment

• Ability to hire, train, and coach a high-performance Customer Success team

• Ability to support the Customer Success Managers’ efforts through strategic advice on account strategies, and serving as executive sponsor with key relationships

• Comfort working cross-functionally, especially with Product, Engineering, and external partners to align marketing goals with product UX and revenue outcomes.

• Creative, resourceful, and fast-moving, with a growth mindset and an eagerness to experiment, learn, and refine strategies quickly.

• Bonus: Familiarity with health, wellness, or benefits-driven platforms, or past work in eCommerce or fintech