Senior Director, Customer Programs (Remote) at Olive

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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 People feel lost in the system today and healthcare employees are essentially working in the dark due to outdated technology that creates a lack of shared knowledge and siloed data.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 is a key leadership position within the Customer Experience Team that manages a team of Customer Program Executives (CPE's). The Senior Director will help drive a world-class customer experience by guiding their team of CPEs who lead the strategy and ownership of complex cross-functional programs with our customers. This is a hands-on coach that leads their team to deliver exceptional strategic account management and on-time program delivery.

When challenges occur, this leader will serve as the first internal and external escalation point for customer issues, working within their team and cross-functionally to remove barriers and provide feedback. This role owns responsibility for the team's overall Pi Delivery (revenue) targets, as well as upsell, renewal, and customer satisfaction metrics. This role requires the ability to mentor individuals, foster a customer-centric execution-focused team culture and drive continuous process improvement to support our growing team.

This role reports to the Senior Vice President of Customer Programs, working closely with stakeholders across the organization.

Essential Duties and Responsibilities:
  • Direct manager of CPE team members and accountability towards key metrics: Pi Delivery (Revenue), renewals, and customer success.
  • Provide strategic advice, coaching, and mentorship to CPE's on customer engagement and customer initiatives to influence organizational strategy, decisions, and programs.
  • Lead efforts to support team retention and growth, including team member onboarding, development of CPE career trajectory resources, supporting recruiting , and development of team culture.
  • Drive a performance-based culture through accountability and foster leadership, strategic thinking, and business acumen on the team.
  • Actively promote change processes to staff and participate in the communication of change initiatives across the organization.
  • Develop, implement and maintain standardized tools, templates, processes, procedures and methodologies to ensure alignment with standards and best practices.
  • Develop, monitor, and report progress on key team performance metrics related to hiring, training / onboarding, staffing, solution identification and delivery.
  • Provide timely feedback to team members to encourage success, ensure accountability, and connect opportunities for team members' development.
  • Drive the ongoing development of a customer-centric culture and team behaviors across the organization, supported by effective policy and process frameworks and compliance tools.
  • Second-level support for program escalations, including participating in service recovery efforts in support of their team and coordinating across divisions within Olive to solve day-to-day challenges.
  • Facilitate cross-functional collaboration with stakeholders to establish vision, objectives, and program strategy.
  • Provide voice of the customer input for Product development and contribute to the ideation, development, and productization of significant new services.


  • Successfully delivered multi-million-dollar programs/projects on-time and on-budget.
  • 10+ years of increasing responsibilities in project management of IT initiatives or other large change initiatives.
  • 5+ years in a client-facing leadership role, ideally leading implementations and support in the healthcare industry, including independently managing multiple complex projects / initiatives with competing priorities and deadlines.
  • Experience with managing direct reports, preferable outside direct customer delivery team relationships, including performance reviews, goal setting, resource prioritization, and playbook/methodology development.
  • Exceptional written and verbal communication skills.
  • 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.
  • Ability to travel up to 50% of the time (travel requirements will vary based on team account assignments and customer needs).
  • Strong analytical and facilitation skills with the ability to interpret and anticipate customer needs in order to develop clear and attainable goals, objectives and execution of project plans.
  • Strong self-starter with entrepreneurial drive and demonstrated ability to achieve stretch goals in a fast-paced, dynamic environment.
  • Outstanding team player with the ability to coordinate people and activities across multiple functional areas.

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
More Information on Olive
Olive operates in the Artificial Intelligence industry. The company is located in Columbus, OH, Denver , CO, Orlando, FL, Chicago, IL, Baltimore, MD and Minneapolis, MN. Olive was founded in 2012. It has 1297 total employees. It offers perks and benefits such as Flexible Spending Account (FSA), Disability Insurance, Dental Benefits, Vision Benefits, Health Insurance Benefits and Life Insurance. To see all 17 open jobs at Olive, click here.
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