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Olive Manager, Implementation Success (Olive Works) - Remote in Boston, Massachusetts

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 People feel lost in the system today and healthcare employees are essentially working in the dark due to outdated technology that creates a lack of shared knowledge and siloed data.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.

Olive Works is one of the core maneuvers of Olive, delivering value to customers through products that span several functional areas and technologies. Olive Works works within Revenue Cycle, Patient Access, Supply Chain, Pharmacy and Clinical functional areas, and works for both payers and providers. Olive Works has a robust set of products, at varying stages of development, deployment and customer adoption.

As Olive continues to blaze a trail in AI and automation programs and solutions in the healthcare space, we are growing our team of Implementation Success Owners (ISOs) to drive solution implementation. As the team grows we are seeking a manager that can provide leadership, direction, guidance and oversight to a segment of the ISO team. ISOs have both the industry knowledge and the technical aptitude to problem solve complex workflows with engineering in addition to stellar communication and project management skills necessary to implement the product in a timely and predictable manner. The leader of this group will need to be highly organized, have a strong sense of ownership, and be willing to work alongside the team to deliver customer success.


  • Responsible for managing a team of 10+ individual contributors and team leads on the ISO team using an agile value delivery mindset

  • Create transparency on status, including challenges and risks for entire portfolio of work to executives and stakeholders across the company

  • Manage the portfolio of assigned work to ensure forecasted dates for work to start and complete are accurate and align with billings and revenue forecasts

  • Work with revenue operations team to understand upcoming pipeline of customers and projects to appropriately understand potential backlog, scope and team capacity

  • Determine team assignments, capacity and resource needs

  • Seek prioritization inputs from stakeholders, facility delivery to commitments and tradeoffs as necessary

  • Act as a main point of escalation for internal team issues and customer facing issues related to the implementation of the product or the CPA

  • Track and report on key performance metrics for implementations (implementation cycle time, lead/lag time, timely delivery, success metrics, etc.)

  • Work with the product team to lead the development of standard templates for tools and materials required to enable successful, repeatable value delivery (ex. project plans, testing plans, customer requirements, etc)

  • Work with the engineering team to understand and provide engineering requirements and surface constraints to customers

  • Manage HR related items for the teams including performance reviews, hiring, disciplinary, team meetings, 1-1s, compensation mgmt, etc.

  • Understand how the product integrates with external systems and partner organizations and ensure the team is following appropriate integrated implementation methodology

  • Collaborate with the Olive Product teams to understand the Olive standard solutions and incorporate current best practices in our solution design work


  • Bachelor’s degree or equivalent professional experience managing healthcare, technology and/or software engineering projects

  • 7+ years of experience managing IT implementation projects in the healthcare sector

  • Experience in healthcare administrative workflow redesign a plus (insurance claims, verification, revenue cycle, supply chain, pharmacy, etc.)

  • Experience building and managing teams, and with HR aspects of team management

  • Expert experience understanding and documenting customer requirements and specifications

  • Excellent cross-team communicator

  • Ability to work independently with moderate supervision in a fast paced, high-growth organization

  • Comfortable suggesting areas for improvement and willingness to lead improvement initiatives

  • Strong written and verbal communication skills, including the ability to communicate complex issues to varying audiences and levels

  • Excellent 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

  • 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

  • Ability to travel up to 30% of the time (travel requirements will vary based on account assignments)

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