Manager, Customer Success

Direct Supply•Milwaukee, WI

About The Position

Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. In the Manager, Customer Success – DS Smart position, you'll lead the day-to-day operations and strategic direction of the DS Smart Customer Success team. You'll coach and develop a growing team of Generalists, Retention Specialists, and Adoption Specialists to drive customer onboarding, adoption, retention, and expansion. This role is pivotal in advancing scalable, technology-enabled workflows, using data and automation to optimize partner performance and unlock greater customer value.

Requirements

5+ years in Customer Success, Customer Experience, or a related customer-facing function
2+ years of people leadership experience
Proven success driving measurable customer outcomes
Strong background in process improvement and workflow design
Proficiency in CRM tools and customer engagement platforms
Excellent communication and coaching capabilities
Ability to travel by car and/or plane up to 10–15%
Valid, unexpired driver’s license with satisfactory driving record
Drives Accountability & Results – Sets clear goals and ensures team members deliver top-notch results. Uses data and tech to boost accountability, pushing everyone to excel individually and as a team.
Applies AI and Technology – Identifies opportunities to boost efficiency and add value using AI and tech. Embraces and applies digital innovations and tech solutions to build business. Eagerly learns and integrates new technologies where they matter most.
Champions Innovation – Propels teams to unlock value with cutting-edge, tech-enabled innovations. Stays ahead of the tech curve, ready to embrace the next big thing. Leads with an entrepreneurial mindset and takes calculated risks.
Leads Through Change & Ambiguity – Navigates the unknown with confidence, steering through change and uncertainty with a clear vision and unwavering determination. Turns chaos into clarity, keeping goals firmly in sight.
Demonstrated ability to lead cross-functional initiatives that optimize operational performance and partner collaboration.
Strong skills in workflow design and process improvement, ensuring scalable and repeatable success.
Deep technical expertise in CRM and customer success platforms to enhance engagement and reporting.
Proven ability to coach and develop high-performing teams, reinforcing feedback, recognition, and career growth.

Nice To Haves

Experience in healthcare technology or supporting multi-site customers
Familiarity with AI tools and automation for customer success
Background in scaling CSM operations in a high-growth SaaS or tech-enabled environment

Responsibilities

Lead the DS Smart Customer Success team, overseeing daily operations, development, and performance management.
Own and continuously refine workflows that drive onboarding, adoption, retention, and customer satisfaction.
Leverage data to measure team success, monitor KPIs, and improve productivity and outcomes.
Champion the use of technology—including AI and automation—to streamline manual tasks and accelerate customer value.
Collaborate with Product, Engineering, Sales, Operations, and other teams to drive alignment and resolve escalations.
Drive results-focused outcomes including fast onboarding, strong 12-week adoption, churn reduction, and scalable customer growth.