Director of Customer Success

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, renewal, 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