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Senior Director, Client Success



Customer Service, Sales & Business Development
Remote · New York, NY, USA
Posted on Tuesday, August 22, 2023


Rightway is on a mission to harmonize healthcare for everyone, everywhere. Our products guide patients to the best care and medications by inserting clinicians and pharmacists into a patient’s care journey through a modern, mobile app. Rightway is a front door to healthcare, giving patients the tools they need along with on-demand access to Rightway health guides, human experts that answer their questions and manage the frustrating parts of healthcare for them.

Since its founding in 2017, Rightway has raised over $130mm from investors including Khosla Ventures, Thrive Capital, and Tiger Global at a valuation of $1 billion. We’re headquartered in New York City, with satellite offices in Miami and Denver. Our clients rely on us to transform the healthcare experience, improve outcomes for their teams, and decrease their healthcare costs.


The Senior Director, Client Success will lead Rightway’s growing Client Success (CS) team within the navigation line of business and will be responsible for the overall retention, satisfaction, and growth of the book of business. This person will work closely with Commercial Sales, Implementation, Service Delivery, Product, Marketing, and others to meet client needs and ensure maximum impact and effectiveness of the CS function.

Accountabilities will include developing CS goals and strategy, optimizing operational processes, developing playbooks and best practices, and leading a high-performing team. This person will also oversee and guide key client relationships and serve as a point of escalation, driving issue resolution internally and externally.

The ideal candidate will be relationship oriented, operationally adept, outcomes minded, poised under pressure, and willing to get hands-on to ensure we not only meet but exceed client expectations.


  • Lead a team of high-performing Client Success Managers and Associates
  • Evolve the current client segmentation and service model for a scaling organization and manage team capacity and staffing
  • Drive and operationalize client renewal, growth (upsell / cross-sell), and retention strategies
  • Build process playbooks, tools, and templates to ensure consistency and scalability of team execution
  • Partner cross-functionally to introduce new processes that optimize internal resources, improve service quality, and enable higher volume output
  • Lead strategic account planning, with involvement from key stakeholders across the organization, and ensure actionable and timely execution on plans
  • Drive team accountability in meeting client deadlines and delivering on key initiatives, such as churn mitigation and member activation
  • Build long-term strategic client partnerships focused on driving significant ROI that result in expanded relationships over time
  • Deepen client feedback and data-gathering and develop strategies to address gap areas
  • Collaborate with Marketing, Service Delivery, Ops, Product, Analytics, etc. on strategic initiatives and client requests, including influencing roadmap for customizations
  • Optimize the client relationship handoff process from Implementation to CS
  • Manage all facets of CS team member onboarding, training, and growth / development
  • Oversee executive-level client relationships and facilitate involvement of Rightway’s executive sponsors in key accounts
  • Drive annual planning process for CS team, including developing goal and KPI targets
  • Travel to important client meetings (e.g., kickoffs) and broker / TPA meetings as relevant


  • 10+ years of relevant experience in client management, consulting (strategy, healthcare, benefits), or operations
  • Minimum 4+ years of experience in the healthcare, health tech, or benefits industry
  • Bachelor’s Degree required
  • Experience leading and developing teams working with complex products
  • Operational excellence and ability to work cross-functionally
  • Has had primary ownership in strategic account relationships for a sustained period
  • Excellent critical thinking skills, combined with the ability to present beliefs clearly and compellingly in verbal and written form, particularly the ability to convey technical / nuanced information in an accessible and understandable manner
  • Ability to juggle several high-priority initiative at once and continuously reprioritize to ensure the most impactful work is accomplished
  • Relationship oriented, with a high degree of comfort managing external stakeholders
  • Adept at presenting in large groups, both in-person and virtually, and managing challenging or escalated client situations
  • Comfortable with ambiguity and motivated to solve complex problems with a creative, can-do mindset
  • Bias towards action
  • Advanced skills in MS Office and/or Google Suite and Salesforce (or other CRM)

Base Salary: $165,000-195,000


We’re seeking those with passion for healthcare and relentless devotion to our goal. We need team members that embody our following core values:

1) We are human, first
Our humanity binds us together. We bring the same empathetic approach to every individual we engage with, whether it be our members, our clients, or each other. We are all worthy of respect and understanding and we engage in our interactions with care and intention. We honor our stories. We listen to—and hear—each other, we celebrate our differences and similarities, we are present for each other, and we strive for mutual understanding.

2) We redefine what is possible
We always look beyond the obstacles in front of us to imagine new solutions. We approach our work with inspiration from other industries, other leaders, and other challenges. We use ingenuity and resourcefulness when faced with tough problems.

3) We debate then commit
We believe that a spirit of open discourse is part of a healthy culture. We understand and appreciate different perspectives and we challenge our assumptions. When working toward a decision or a new solution, we actively listen to one another, approach it with a “yes, and” mentality, and assume positive intent. Once a decision is made, we align and champion it as one team.

4) We cultivate grit
Changing healthcare doesn’t happen overnight. We reflect and learn from challenges and approach the future with a determination to strive for better. In the face of daunting situations, we value persistence. We embrace failure as a stepping stone to future success. On this journey, we seek to act with guts, resilience, initiative, and tenacity.

5) We seek to delight
Healthcare is complicated and personal. We work tirelessly to meet the goals of our clients while also delivering the best experience to our members. We recognize that no matter the role or team, we each play a crucial part in our members’ care and take that responsibility seriously. When faced with an obstacle, we are kind, respectful, and solution-oriented in our approach. We hold ourselves accountable to our clients and our members’ success.

Rightway is a healthcare company looking to improve healthcare outcomes for everyone, everywhere. With that in mind, we have to consider what is good for the health of our team, the company, and the communities we operate in. As such, Rightway has determined a mandatory COVID-19 vaccination policy for all employees, in combination with other safety precautions, is the best way forward.

Rightway is PROUDLY an Equal Opportunity Employer that believes in strength in the diversity of thought processes, beliefs, background and education and fosters an inclusive culture where differences are celebrated to drive the best business decisions possible. We do not discriminate on any basis covered by appropriate law. All employment is decided on the consideration of merit, qualifications, need and performance.