Remote Senior Mid‑Market Customer Success Manager

OpenLoop Health; United States; Remote; USD 90,000 - 120,000; Full time

Job summary

OpenLoop Health is seeking a Senior Customer Success Manager (Mid-Market) to manage a growing remote portfolio. You will own renewal strategies, drive retention and expansion, and partner with Implementation, Support, Sales, and Product to ensure customer value realization.

The role emphasizes structured adoption planning, measurable outcomes, and proactive risk management across multiple stakeholders to minimize churn and maximize platform utilization.

Qualifications

• 4–6+ years of Customer Success or Account Management experience (B2B SaaS preferred)
• Strong renewal and revenue retention track record
• Structured success planning and measurable adoption outcomes
• Experience navigating multiple decision-makers across teams
• Ability to analyze performance trends and translate into strategic recommendations
• Anticipates risks and acts before issues impact retention
• Familiarity with healthcare delivery models or telehealth ecosystems is a plus

Responsibilities

• Own renewal strategy and identify expansion opportunities across your mid-market portfolio
• Develop and execute clear success plans to ensure customers achieve defined outcomes and maximize platform utilization
• Build and maintain relationships across accounts, ensuring alignment on goals and performance
• Proactively manage the end-to-end renewal process, mitigating churn risk through early health monitoring and engagement tracking
• Surface upsell triggers and collaborate with Sales to execute expansion opportunities aligned with customer value realization
• Conduct recurring business reviews to communicate performance, ROI, and growth opportunities, using trend analysis to guide recommendations
• Translate customer feedback and recurring themes into actionable insights for Product and Leadership
• Partner with Implementation, Support, Sales, and Product to ensure smooth onboarding, adoption, and issue resolution
• Monitor engagement signals, proactively address risk, and implement recovery plans before churn risk escalates

Skills

Renewal strategy

Revenue retention

Account management

Adoption planning

Cross-functional

Performance analysis

Risk management

Telehealth familiarity

Job description

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 Senior Customer Success Manager (Mid-Market) to join our team remotely. In this role, you will manage a portfolio of growing mid-market accounts, ensuring customers achieve measurable outcomes while driving retention and expansion within your book of business.

You will serve as a strategic partner to multiple stakeholders, guiding adoption, proactively managing renewals, and identifying opportunities to expand OpenLoop’s solutions in alignment with client goals. This role requires strong commercial acumen, structured adoption planning, and the ability to manage moderate account complexity at scale.

What You’ll Do

• Own renewal strategy and identify expansion opportunities across your mid-market portfolio

• Develop and execute clear success plans to ensure customers achieve defined outcomes and maximize platform utilization

• Build and maintain relationships across accounts, ensuring alignment on goals and performance

• Proactively manage the end-to-end renewal process, mitigating churn risk through early health monitoring and engagement tracking

• Surface upsell triggers and collaborate with Sales to execute expansion opportunities aligned with customer value realization

• Conduct recurring business reviews to communicate performance, ROI, and growth opportunities, using trend analysis to guide recommendations

• Translate customer feedback and recurring themes into actionable insights for Product and Leadership

• Partner with Implementation, Support, Sales, and Product to ensure smooth onboarding, adoption, and issue resolution

• Monitor engagement signals, proactively address risk, and implement recovery plans before churn risk escalates

Who You Are

• 4–6+ years of Customer Success or Account Management experience (B2B SaaS preferred), with demonstrated success in renewal and revenue retention

• Comfortable managing contracts, renewal conversations, and expansion discussions

• Experienced in structured success planning and driving measurable adoption outcomes

• Skilled at navigating multiple decision-makers and aligning priorities across teams

• Able to analyze performance trends and translate insights into strategic recommendations

• Anticipates risks and acts before issues impact retention

• Familiarity with healthcare delivery models or telehealth ecosystems is a plus

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.