Senior Director, Customer Success

American Well; Boston (MA); Remote; USD 171,000 - 242,000; Full time

Job summary

A leading healthcare technology company in Boston is seeking a Senior Director of Customer Success to enhance customer engagement and drive value realization. Responsibilities include developing a customer success program, managing executive relationships, and leading a high-performing team. Ideal candidates should have significant experience in customer success, particularly in healthcare IT, and exhibit strong leadership and analytical skills. This role offers a competitive salary and flexible working arrangements.

Benefits

Flexible Personal Time Off

401K match

Competitive healthcare, dental and vision insurance

Paid maternity and parental leave

Employee Stock Purchase Program

Free Telehealth Services

Tuition Assistance Program

Pet Insurance

Qualifications

• 10+ years leading a large-scale customer success organization.
• Experience at a high growth company with distributed operations.
• Seasoned people leader with experience developing mid-level managers.

Responsibilities

• Develop and operationalize a scaled, digital-first success program.
• Build and maintain trusted executive relationships with key customer stakeholders.
• Drive use-case optimization and product consulting.

Skills

Analytical thinking

Customer service skills

Interpersonal skills

Troubleshooting skills

Leadership

Communication skills

Education

Bachelor's Degree in Business Administration, Economics, Finance, or related field

Tools

Gainsight

Salesforce

Job description

Company Description

Amwell digitally empowers payers, providers and innovators, enabling an ecosystem of care that spans across in-person, virtual and automated care.

Amwell provides a leading hybrid care enablement platform in the United States and globally, connecting and enabling providers, payers, patients, and innovators to deliver greater access to more affordable, higher quality care.

Amwell believes that hybrid care delivery will transform healthcare. The company offers a single, comprehensive platform to support all digital health needs from urgent to acute and post-acute care, as well as chronic care management and healthy living.

With nearly two decades of experience, Amwell powers the hybrid care of more than 55 health plans, which collectively represent more than 90 million covered lives, and many of the nation's largest health systems, representing over 2,000 hospitals, have access to Amwell solutions.

Brief Overview

The Senior 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

Additional information

Job Level: M6

Working at Amwell

Amwell is changing how care is delivered through online and mobile technology. We strive to make the hard work of healthcare look easy. In order to make this a reality, we look for people with a fast-paced, mission-driven mentality. We're a culture that prides itself on quality, efficiency, smarts, initiative, creative thinking, and a strong work ethic.

Our Core Values include One Team, Customer First, and Deliver Awesome. Customer First and Deliver Awesome are all about our product and services and how we strive to serve. As part of One Team, we operate the Amwell Cares program, which brings needed assistance to our communities, whether that be free healthcare for the underserved or for people affected by natural disasters, support for equality, honoring doctors and nurses, or annual Amwell-matched donations to food banks. Amwell aims to be a force for good for our employees, our clients, and our communities.

Amwell cares deeply about and supports Diversity, Equity and Inclusion. These initiatives are highlighted and reflected within our Three DEI Pillars - our Workplace, our Workforce and our Community.

Amwell is a 'virtual first' workplace, which means you can work from anywhere, coming together physically for ideation, collaboration and client meetings. We enable our employees with the tools, resources and opportunities to do their jobs effectively wherever they are!

The typical base salary range for this position is $171000- $242000. 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.

Additional Benefits

• Flexible Personal Time Off (Vacation time)
• 401K match
• Competitive healthcare, dental and vision insurance plans
• Birthing parents at Amwell enjoy up to 18 weeks of paid maternity leave
• Non-birthing parents enjoy 10 weeks of paid leave
• US employees experiencing reproductive loss are eligible for up to 7 days of paid 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