Customer Enablement Specialist, Healthcare

About Roundstone

Founded in 2003, Roundstone is not your typical insurance company. We’re on a mission to help employers save on healthcare benefits so they can put those savings towards bettering their businesses and taking care of their employees.

About the Role

The Customer (Employer) Enablement Specialist is a growth-enabling operations role that improves conversion, engagement, and retention of partner programs by ensuring Employers and Brokers understand Roundstone’s ecosystem partner programs and use them. This role combines onboarding, education, and adoption analytics to drive strategic value. The team member is accountable for the onboarding and offboarding of clients into partner programs and systems, with a focus on accelerating adoption, increasing user engagement, and driving measurable pull-through within each client. This role serves as the operational bridge between clients, internal teams, and partner stakeholders, ensuring a smooth implementation experience, effective education, and clear tracking of outcomes. The function combines onboarding execution, change management, and adoption analytics to improve time-to-value and support long-term program success.

Responsibilities

• Facilitate end-to-end Employer onboarding into partner programs, systems, and workflows in collaboration with COM and Onboarding.
• Manage client offboarding processes to ensure clean transitions, accurate data handoff, and closure of access or program participation.
• Educate Employer stakeholders on program purpose, system use, workflow expectations, and success criteria.
• Develop onboarding materials, training guides, FAQs, and adoption resources in collaboration with the Vendor Manager and Partner.
• Support Employer and Partner quarterly business reviews to reinforce value, drive engagement, and recommend next-step actions.
• Maintain clear dashboards and reporting on onboarding progress, adoption trends, and outcome metrics.
• Support tracking of adoption, utilization, and pull-through at the client and end-user level with Customer Success and Partners.
• Identify adoption barriers and work cross-functionally to remove operational, technical, or communication gaps.
• Partner with customer success, operations, product, and sales teams to align execution and escalation paths.

Qualifications

• 3+ years of experience in client success, implementation, program management, operations, or related roles.
• Strong project management and cross-functional coordination skills.
• Experience educating clients and driving adoption of products, programs, or systems.
• Comfort working with operational metrics, dashboards, and performance reporting.
• Ability to manage multiple clients and priorities while maintaining a high level of detail.
• Experience in healthcare, insurance, benefits, or partner-driven programs preferred.

Benefits

• Medical, dental, and vision benefits
• Annual bonus
• Dependent care 100% match up to max allowable
• Parental leave
• PTO beginning on Day 1
• Tuition reimbursement
• Hybrid office schedule
• 401(k) plan with company match
• Employee Assistance Program
• On-site gym with personal trainer access
• Life insurance and short-term disability insurance

About the Company

Headquartered in Rocky River, Ohio, Roundstone is proud to be a Northeast Ohio Top Workplace as recognized by The Plain Dealer and cleveland.com, based on anonymous employee feedback. We foster a supportive, values-driven culture where employees feel engaged, valued, and celebrated. Roundstone has also been named an Inc. 5000 award recipient for eight consecutive years, reflecting our continued growth and success.

Our Core Values:

• Live well: Be healthier and bring positive energy to all you do.
• Work smarter: Get things done, better.
• Own it: Accountability is your middle name. Be on time, do what you say, and finish what you start.
• Be intellectually curious: Always be learning. See opportunity everywhere and have a drive to know.