Senior Project Manager, Service Delivery

Support the Service Delivery organization by leading client‐facing benefits administration initiatives focused on service delivery excellence, operational readiness, and annual enrollment (AE).

This role requires a strong understanding of benefits administration products and platforms, hands‐on experience servicing clients, and proven success leading projects that directly impact client outcomes. You will partner closely with service delivery, implementation, product, and technology teams to ensure high‐quality execution, on‐time delivery, and an exceptional client experience.

The Senior Project Manager plays a critical role in driving successful client engagements, improving delivery consistency, and supporting long‐term client satisfaction, retention, and growth.

Reasonable accommodations may be made to enable individuals with disabilities to perform these essential functions.

Client‐Facing Benefits Administration Project Leadership

Lead and manage client‐facing projects within a benefits administration environment, ensuring alignment between client expectations, service delivery teams, and cross‐functional partners.

Drive projects related to client onboarding, ongoing service delivery enhancements, platform configuration, operational readiness, and annual enrollment execution.

Act as a primary project leader supporting Service Delivery teams by proactively identifying risks, managing dependencies, and resolving issues that may impact client timelines or experience.

Ensure all client initiatives align with defined goals related to client health, satisfaction, retention, and long‐term partnership success.

Serve as a trusted partner to internal delivery teams to ensure clarity, accountability, and high standards of execution for client commitments.

Annual Enrollment (AE) & Service Delivery Initiatives

Lead or support annual enrollment–related client projects, including planning, cross‐team coordination, readiness tracking, execution support, and post‐AE analysis.

Coordinate closely with service delivery, technology, product, and operations teams to ensure smooth execution during high‐volume, time‐sensitive benefit cycles.

Apply strong organizational, prioritization, and communication skills to manage competing client needs and mitigate risk during peak enrollment periods.

Support continuous improvement in AE execution by identifying lessons learned and opportunities to enhance future client delivery.

Integrated Client Project Management & Execution

Develop, maintain, and execute detailed client‐facing project plans using Smartsheet as a primary tool, along with Jira and other project management platforms as needed.

Apply Agile, Scrum, or Waterfall methodologies based on client needs, scope, and delivery timelines.

Facilitate effective collaboration across service delivery teams, internal delivery partners, and external vendors supporting client initiatives.

Track and manage project timelines, risks, issues, and dependencies to ensure successful client outcomes.

Communicate project status, milestones, risks, and outcomes clearly and consistently to stakeholders, with a strong focus on client impact and delivery readiness.

Bachelor’s degree required; advanced degree preferred.

5–10 years of experience working with benefits administration products and platforms in a client‐facing or service delivery environment.

Demonstrated experience servicing external clients and leading client‐driven initiatives within benefits administration or benefits technology.

2–5 years of direct project management experience managing complex, cross‐functional, client‐facing initiatives.

Strong understanding of service delivery models, operational workflows, and annual enrollment cycles.

Proficiency with Smartsheet (strongly required), Jira, and related project management tools.

Working knowledge of Agile, Scrum, and Waterfall methodologies.

Exceptional communication, organization, and stakeholder‐management skills with a strong client service mindset.

Ability to work independently in a remote environment while managing multiple client priorities.

PMP certification.

Experience leading or supporting client annual enrollment projects at scale.

Background in benefits technology, consulting, or SaaS environments.

Experience managing complex client implementations or service delivery transformations.

Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities required for this job. Duties, responsibilities, and activities may change at any time with or without notice.