Posted a month ago

Olive’s AI workforce is built to fix our broken healthcare system by addressing healthcare’s most burdensome issues -- delivering hospitals and health systems increased revenue, reduced costs, and increased capacity. People feel lost in the system today and healthcare employees are essentially working in the dark due to outdated technology that creates a lack of shared knowledge and siloed data. Olive is designed to drive connections, shining a new light on the broken healthcare processes that stand between providers and patient care. She uses AI to reveal life-changing insights that make healthcare more efficient, affordable and effective.

Olive’s vision is to unleash a trillion dollars of hidden potential within healthcare by connecting its disconnected systems. Olive is improving healthcare operations today, so everyone can benefit from a healthier industry tomorrow.

Job Overview:

The Senior Director of Customer Programs (Payer) has the primary responsibility of leading and developing the Customer Experience program for Olive’s Payer customers. This role will include integration of our current Customer Experience methodology into our Payer customers as well as tweaking that methodology, where appropriate, for this unique group of customers. In addition, this role will lead one or more of our Payer customer programs directly, serving as a Customer Program Executive, while growing and developing other team members focused on the Payer market.

Customer Program Executives lead strategy and ownership of highly complex, cross-functional programs while collaborating with subject matter experts and key stakeholders to achieve vision, objectives, and develop program strategy. They manage resources which may include people, data, processes, and third party relationships. They are responsible for initiating and developing relationships with internal and external stakeholders and providing advisory services and support to achieve program goals.

In addition to the Customer Program Executive role, the Sr. Director also leads cross-functional process and program improvement efforts and sets and manages the financial plan for customer programs in the Payer market. This role will continue to build the Payer-focused team via recruiting and onboarding, implementing and managing tools to support the operations, utilizing the OliveWay for consistent delivery of customer commitments, and supporting teams to successfully implement and secure renewals of automation programs.

Success in this role hinges on strong leadership and drive for results, while balancing stakeholder requirements, with a strong understanding of Olive business priorities, sales process, customer perceptions and considerations, as well as the competitive landscape.

Primary Responsibilities

  • Serve as the accountable driver of effective relationships and ensure the successful implementation and delivery of Olive programs
  • Establish and facilitate a governance, risk, communications, and operational program consisting of Customer and Olive leadership to effectively oversee the program
  • Innovate service and operational solutions to best achieve customer goals and accountable for driving high levels of customer satisfaction, retention, and growth
  • Ensure strong, effective relationships with customer executive leadership and key internal operational leaders, in order to best understand the customer's goals, operational environment, and strategic initiatives
  • Monitor and track all aspects of the project, including productivity milestones, deliverables, and timelines
  • Preemptively address customer needs, critical issues and risks, and present options for addressing/solving needs and issues
  • Facilitate cross-functional collaboration with stakeholders to establish vision, objectives, and program strategy
  • Actively seek out and solve for barriers / problems / risks to successful delivery of program objectives
  • Realize, articulate, and communicate growth opportunities within existing customers. Facilitate change orders and new sales opportunities with sales team for any customer service requests outside of contracted services.
  • Provide voice of the customer input for Product development and contribute to the ideation, development, and productization of significant new services
  • Lead identification of customer needs and supporting solutions, including co-creation of new solutions, where necessary
  • Regularly provide updates on work progress, obstacles and blockers, and overall performance with execution and progress toward delivery
  • Drive a performance-based culture through accountability and foster leadership, strategic thinking, and business acumen on the team
  • Provide timely feedback to team members to encourage success, ensure accountability, and connect opportunities for team members' development
  • Lead initiatives to support team retention and growth, including team member onboarding, development of career trajectory resources, supporting recruiting efforts/strategy, and development of team culture
  • Actively promote change processes to staff and participate in the communication of change initiatives across the organization. Identify cultural barriers to change and implement strategies to address these.
  • Provide strategic advice, counsel and recommendations on customer engagement and experience matters to influence organizational strategy, decisions, and initiatives
  • Work with active implementation teams to advise on program strategy, resource alignment, and ensure positive progress


  • Successfully delivered multi-million-dollar programs/projects on-time and on-budget
  • 10+ years of increasing responsibilities in project management of complex product implementations, IT initiatives or other large change initiatives, specifically in the healthcare payer space
  • 10+ years in a customer facing role, ideally leading implementations and support in the healthcare industry, including independently managing multiple complex projects/initiatives with competing priorities and deadlines
  • 10+ years of experience with analyzing and synthesizing qualitative and quantitative information, forming opinions with corresponding recommendations, and presenting the results to key stakeholders including executive leadership
  • Demonstrated ability to communicate analysis, including trends and opportunities, to leadership and stakeholders
  • Articulate, assertive and persuasive with the ability to adapt communication style and approach to audiences at all levels
  • Proven problem-solving skills, including balancing multiple priorities and addressing team and/or prioritization conflicts
  • Prior experience leading, managing and collaborating with cross-functional teams, business partners and stakeholders
  • Ability to work independently and be resourceful when confronted with ambiguity.
  • Strong change management knowledge and/or experience
  • Effective organizational skills and attention to detail, and ability to prioritize/organize/multitask and meet multiple deadlines
  • Proficiency with evaluating, bench-marking and improving business processes

At Olive, we're committed to growing and empowering an inclusive community within our company and industry. This is why we hire and cultivate diverse teams of the best and brightest from all backgrounds, experiences, and perspectives across our organization. Research shows that oftentimes women and other minority groups only apply to open roles if they meet 100% of the listed criteria. Olive encourages everyone — including women, people of color, individuals with disabilities and those in the LGBTQIA+ community — to apply for our available positions, even if they don't necessarily check every box on the job description.


This job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee. Duties, responsibilities and activities may change or new ones may be assigned.

This job description does not constitute a contract of employment and Olive AI, Inc. may exercise its employment-at-will rights at any time


We take the health and happiness of our employees seriously and consistently evaluate new ways to provide an amazing place to work. From retirement planning, to a wellness program designed to actively incorporate mental and physical wellness into daily interactions amongst fellow Olivians, we make sure to take care of our own.

  • Health, Dental, and Vision insurance that starts on your first day at Olive with 100% of premiums covered for team members and 75% covered for dependents
  • Monthly Grid stipend to cover work related expenses
  • Unlimited PTO
  • Telemedicine
  • EAP/Mental health resources
  • Getaways by Marriott Bonvoy
  • Family-building and fertility support via Kindbody
  • 12 weeks of parental leave
  • 401(K) match
  • Wellness program
  • Stock Options
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Senior Director Customer Programs - Payer