Brief Overview 

The Director of Customer Success is a strategic, customer-obsessed leader responsible for driving adoption, value realization, and long-term partnership across Amwell’s customer portfolio. This role will define and execute a scaled, digital-first success model that deepens engagement, strengthens retention, and maximizes customer outcomes.

Reporting to the SVP of Growth Operations & Customer Experience, this leader will partner closely with Sales, Product, Support, and Operations to ensure that every customer — from implementation through renewal — experiences measurable impact from the Amwell platform.

Core Responsibilities 

· Customer Strategy & Engagement

· Develop and operationalize a scaled, digital-first success program that delivers proactive, value-driven engagement at every stage of the customer lifecycle.

· Build and maintain trusted executive relationships with key customer stakeholders, serving as a strategic advisor on adoption, utilization, and business impact.

· Partner with Sales and Product to align customer outcomes with account growth and platform innovation priorities.

· Lifecycle & Value Realization

· Lead efforts to move customers from onboarding to proficiency and advocacy within the Amwell product suite.

· Drive use-case optimization, provider engagement, and product consulting that tangibly improve performance and satisfaction.

· Monitor customer health in Gainsight and develop data-driven playbooks for risk mitigation, upsell opportunity, and proactive outreach.

· Collaboration & Escalation Management

· Serve as the central point of communication for complex support escalations, ensuring fast resolution and strong cross-functional alignment.

· Partner with Customer Support and Product to identify root causes, eliminate recurring issues, and improve customer experience end-to-end.

· Leadership & Measurement

· Coach and develop a high-performing Customer Success team, fostering accountability, empathy, and operational excellence.

· Define and report on key metrics including adoption, health, retention, and NPS — using insights to continuously improve both strategy and execution.

Qualifications

· Bachelor’s Degree in Business Administration, Economics, Finance, or related field of study required

· 10+ years leading a large-scale customer success organization at a well-regarded brand, preferably in the healthcare IT space

· Experience at a high growth company with distributed operations

· Analytical thinker with strong troubleshooting skills and the ability to think systematically

· Demonstrated success scaling an operation while elevating the customer experience

· Seasoned people leader with experience developing mid-level managers and directors

· Excellent interpersonal and customer service skills

· Comfortable understanding and explaining software products to diverse audiences

· High energy level, enthusiastic, and eager to do what is necessary to be successful

· Excellent verbal and written communication skills

· Willing to work unpredictable hours and work against tight deadlines

· Experience with Gainsight and Salesforce preferred

Do Well. Live Well. At Amwell. 

Driven by our mission and values, we foster a workplace where Delivering Awesome, being Customer First and operating as One Team aren’t just aspirations – they are how we work, every day.  

Our people are our greatest asset. We strive to empower their growth and development not only as Amwellians but as individuals, through generous total rewards packages, a virtual-first work environment, work-life flexibility, including Summer Fridays and designated Mental Health Days, as well as opportunities to stretch and learn – to name a few. It’s our people who truly differentiate us. Ask anyone and they’ll tell you – you’ll never work with more passionate, more driven and more caring team members.    

We champion a culture of respect and inclusion, accountability and integrity, innovation and collaboration. At Amwell, you’ll do the most meaningful work of your career—improving healthcare for millions, growing alongside incredible teammates, and being valued for who you are.  

Benefits 

• Flexible Personal Time Off (Vacation time)
• 401K match
• Competitive healthcare, dental and vision insurance plans
• Paid Parental Leave (Maternity and Paternity leave)
• Employee Stock Purchase Program
• Free access to Amwell’s Telehealth Services, SilverCloud and The Clinic by Cleveland Clinic’s second opinion program
• Free Subscription to the Calm App
• Tuition Assistance Program
• Pet Insurance 

Salaried, Exempt Roles

The typical base salary range for this position is $156,240 - $195,300.  The actual salary offer will ultimately depend on multiple factors including, but not limited to, knowledge, skills, relevant education, experience, complexity or specialization of talent, and other objective factors.  In addition to base salary, this role may be eligible for an annual bonus based on a combination of company performance and employee performance. Long-term incentive and short-term variable compensation may be offered as part of the compensation package dependent on the role. Some roles may be commission based, in which case the total compensation will be based on a commission and the above range may not be an accurate representation of total compensation.

Further, the above range is subject to change based on market demands and operational needs and does not constitute a promise of a particular wage or a guarantee of employment. Your recruiter can share more during the hiring process about the specific salary range based on the above factors listed.

https://business.amwell.com/company/privacy-notice-applicants