Head of Project Management; Remote

Be part of a team that unleashes the power of leading-edge technologies to help improve the health and well-being of those most vulnerable in our country and communities. You’ll add to your technical credentials and certifications while enjoying a generous, flexible vacation policy and educational assistance. We also have comprehensive leadership and technical development academies to help build your skills and capabilities.

The Operational Readiness & Review (ORR) Lead role oversees the readiness assessment, demonstrations, cutover, and increased customer service of one or more legacy systems into one or more Gainwell solutions. Specifically working in Medicaid systems, the Operational Readiness & Review Lead will ensure the proper transition by partnering with multiple third parties, internal teams, and account Subject Matter Experts (SMEs).

This lead position will ensure that solutioned systems are appropriately understood, documented, and prepared for transition, while simultaneously ensuring communication meets both Gainwell’s standards along with the clients’ expectations.

Perform Operational Readiness Demonstrations, where the ORR Lead facilitates meetings directly with the client to showcase business results

Maintain an Operational Readiness Assessment across multiple vendors and internal teams to migrate from a series of legacy systems over to a series of new implementations, following defined project management policies and procedures and leading project teams that are responsible for achieving project/program objectives

Develop, update, and maintain a series of reports and checklists, including but not limited to the following documents:

Organizes, directs, and motivates project team members to ensure awareness and understanding of ORR deadlines, scope, assignments, and objectives and to successfully execute and deliver upon those expectations

Effectively communicates project progress to workstream leadership through updates including identifying, communicating, and monitoring Risks, Assumptions, Issues, Dependencies, and Constraints

Five or more years of experience in project and / or program management or equivalent leadership experience, with specific “hands on” experience managing, and successfully delivering, multiple projects and/or programs of varying size and complexity

Exceptional communication skills, both verbal and written, with the ability to effectively communicate project status, progress, and challenges to multiple-level stakeholders

Experience adapting to changes in priority and the ability to “think on your feet” when circumstances/issues arise, with the mindset/ability to focus on the resolution of the problem and motivate the project team to do likewise

Experience managing projects within a Client / Vendor structure

Project Management Professional (PMP) certification preferred

Remote-based opportunity within the United States

Opportunities to travel through your work (0-10%)

Video cameras must be used during all interviews, as well as during the initial week of orientation

The deadline to submit applications for this posting is 11/30/2026

The pay range for this position is $86,800.00 - $ per year, however, the base pay offered may vary depending on geographic region, internal equity, job-related knowledge, skills, and experience among other factors. All salaried, full-time candidates are eligible for our generous, flexible vacation policy, a 401(k) employer match, comprehensive health benefits , and educational assistance. We also have a variety of leadership and technical development academies to help build your skills and capabilities.

You’ll be joining a company where collaboration, innovation, and inclusion fuel our growth. Learn more about Gainwell at our…