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 People feel lost in the system today and healthcare employees are essentially working in the dark due to outdated technology that creates a lack of shared knowledge and siloed data.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

Job Overview:

The Customer Success Manager at Olive is part of the Customer Experience Org and will work to ensure the customer is set up for and experiences a successful automation journey from contract start through the duration of the Olive relationship. The Customer Success Manager must effectively deliver and advise on best practices and provide proactive communications. They are responsible for reporting on the value Olive is generating. This role will work with customers, the Olive account team, and product/analytics teams to help proactively deliver, communicate successes and value with the customers. Experience implementing complex healthcare solutions and helping drive customer satisfaction is desired for this role.

Essentials Duties & Responsibilities:

  • Responsible for customer onboarding and automation readiness. Ensure the automation journey stays on-track assess customers for readiness, assist in removing barriers, and ensure a seamless automation journey

  • Product adoption and articulation of value. Advise product on market feedback (structured feedback). Understand the business impact that Olive’s work is having and provide insights and reports that measure or track the value that is being generated

  • Align with support in addressing issues and blockers to minimize downtime

  • Support growth efforts by evangelizing successes from our partner ecosystem (the Library)

  • Provide feedback to account/sales on key performance indicators, risks, and future opportunities

  • Provide customers with regular reporting and information that gives visibility into Olive’s performance

  • Drive internal improvement activities including operational processes and consulting methodology

  • Partner with Product (and other areas) to drive Olive solutions in directions our customers need

  • Perform strategy or quarterly business reviews with customers

  • Highlight areas and opportunities for Olive to expand her work or for the customer to expand their digital workforce


  • Experience on customer-facing teams managing multi-million-dollar healthcare programs/projects

  • 7+ years of client-facing project management/account management experience in healthcare software or consulting environment (e.g. lead meetings, draft status reports, develop & manage project plans, track issues/risk logs, develop & monitor resource plans, etc.)

  • 3+ years in, leading complex healthcare implementations and support efforts; experience working on or leading large-scale CIS (Epic, Cerner, Allscripts, MEDITECH, McKesson) implementation initiatives, including the development of documentation templates, training plans, and implementation plans

  • 2+ 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

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

  • Experience leveraging data to understand customer performance and drive desired outcomes

  • Self-starter with the ability to appropriately prioritize and strategize effectively in a rapidly changing environment

  • Strong communication and analytical skills with an ability to creatively solve problems in a fast-paced startup environment

  • Ability to collaborate and influence stakeholders (internal and external) to ensure a successful customer experience

  • Travel may be required up to 40% to visit customers and/or attend internal meetings

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 paid parental leave

  • 401(K) match

  • Wellness program

  • Stock Options