Sr. Project Manager (Benefits Administration)

TL;DR

Sr. Project Manager (Benefits Administration): Driving client-facing benefits administration initiatives and enterprise-level internal programs with an accent on service delivery, operational readiness, and annual enrollment. Focus on leading complex cross-functional projects, managing risks and dependencies, and ensuring high-quality execution during high-volume periods.

Location: Remote, United States. Standard working hours 8am-5pm Central Time.

Salary: $110,000-$135,000

Company

Cloud-based benefits administration platform empowering employees to manage benefits, serving thousands of companies nationwide from Chicago.

What you will do

• Lead client-facing projects in benefits administration, aligning client expectations with service delivery and stakeholders.
• Drive annual enrollment projects, including planning, coordination, readiness tracking, and post-analysis.
• Manage internal enterprise programs for technology implementations, process optimization, and operational efficiency.
• Develop and execute project plans using Smartsheet, Jira, and methodologies like Agile, Scrum, or Waterfall.
• Track timelines, budgets, risks, and dependencies; communicate status to stakeholders.

Requirements

• Bachelor’s degree required; 5–10 years in benefits administration products, client-facing or service delivery.
• 2–5 years direct project/program management of complex initiatives.
• Strong understanding of service delivery, operational workflows, annual enrollment cycles.
• Proficiency with Smartsheet (required), Jira, project management tools; Agile/Scrum/Waterfall knowledge.
• Exceptional communication, organization, stakeholder management; ability to work independently remotely.

Nice to have

• PMP certification.
• Experience leading large-scale annual enrollment projects.
• Background in benefits technology, consulting, or SaaS.
• Enterprise-level change or operational improvement initiatives.

Culture & Benefits

• Remote first, office friendly environment.
• Comprehensive health, dental, vision plans; retirement savings with employer match.
• Competitive compensation with performance incentives.
• Professional development, training resources.
• Supportive culture emphasizing collaboration, wellbeing initiatives, work-life balance.