Director of Customer Success

About OpenLoop OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states. About the Role OpenLoop is looking for a Director of Customer Success to join our team remotely or at our HQ in Des Moines, IA. In this role, you will lead, mentor, and manage a team of Customer Success Managers responsible for driving net revenue retention through adoption, retention, and expansion across a scaled, digital-first customer success motion. You will set strategy and standards for lifecycle programs, segmentation models, and data-driven engagement, while coaching your team to execute effectively using automation, health scoring, and targeted human touchpoints to deliver measurable customer and revenue outcomes in a fast-growing digital health environment. What You'll Do Own the scaled CS strategy for SMB and mid-market customers, balancing digital engagement with targeted human touchpoints. Design and optimize digital customer journeys across onboarding, adoption, renewal, and expansion. Build and manage segmentation and coverage models (digital-only, pooled, hybrid). Own health scoring frameworks, lifecycle triggers, and in-app / automated outreach. Partner with Product and Marketing to deliver in-product education, campaigns, and self-serve resources. Drive retention and expansion through programmatic, data-driven plays. Lead a team of Scaled / Digital CSMs and CS Ops partners. Drive KPIs (GRR, NRR, adoption, engagement) and report performance to leadership. Continuously test, measure, and iterate on scalable CS programs. Who You Are 7+ years of experience in Customer Success, CS Operations, or Growth roles. 3+ years of experience leading and developing customer-facing teams, ideally in a scaled or digital CS environment. Proven track record of owning and improving NRR in a SaaS or digital health business. Strong experience with customer success platforms (Gainsight, Totango, ChurnZero, or similar). Highly data-driven, comfortable with experimentation, automation, and iterative improvement. Experience operating in fast-growing or startup environments with evolving processes. Our Benefits In addition, for salaried positions you would also be eligible for: Medical, Dental, and Vision plans Flexible Spending/Health Savings Accounts Flexible PTO 401(k) + Company Match Life Insurance, Pet insurance, and more Our Company We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work. Sound like a good fit? We’d love to meet you.