Via Benefits Accounts: Project Manager

WTW•Chicago, IL

18d•Remote

About The Position

At WTW, we strive to be the best company for our colleagues and clients. As a global leader in people, risk, and capital management, we bring together the industry's top talent to deliver innovative solutions. Join us to collaborate with inspiring colleagues, grow your career, and make a meaningful impact. The Role We are seeking a proactive, results-driven Project Manager to join WTW’s spending account administration team. This role requires a project manager who takes ownership of outcomes, not just coordination of activities, and who is comfortable driving initiatives forward across functional teams and leadership levels. The Project Manager will operate in a dynamic environment where initiatives frequently span multiple business and technology team, and requirements or scope may not be fully defined at the onset of the projection. The successful candidate will be comfortable creating structure where needed, aligning diverse stakeholders, and advancing work even on projects with little definition to start. In this role, you will lead multiple operational initiatives that support the Spending Account Administration business, driving projects from early definition through execution and ensuring initiatives maintain momentum and deliver meaningful outcomes. The Project Manager is expected to proactively identify next steps, drive alignment, and move initiatives forward without relying on detailed direction. This position requires a high degree of ownership and self-direction and the ability to effectively manage multiple projects at the same time.

Requirements

Bachelor’s degree or equivalent experience.
3-5+ years of project management experience leading cross-functional business and technology initiatives.
Proficiency with Microsoft Word, PowerPoint, Excel, and project planning tools such as Microsoft Project.
Demonstrated ability to independently drive initiatives from ambiguity through execution.
Proven ability to influence stakeholders and drive decision-making across cross-functional teams and leadership levels.
Highly organized with strong time-management skills and the ability to manage multiple priorities simultaneously.
Strong judgment in prioritizing work and balancing competing business needs.
Strong business acumen and the ability to understand operational and technology implications of initiatives.
Comfortable operating in evolving environments where processes and governance are still being established.
Clear and confident communicator capable of engaging diverse audiences, including senior leadership.
Resilient under pressure with strong problem-solving and decision-making abilities.
Candidate’s schedule must be flexible enough to cover most Eastern time zone business hours.

Nice To Haves

Professional project management certifications (PMP, PRINCE2, etc.) are a bonus but are not required.
Familiarity with spending account administration or employee benefits outsourcing is preferred but not required.

Responsibilities

Lead cross-functional projects from initiation through completion, ensuring initiatives deliver measurable outcomes aligned with business objectives.
Define project scope, structure, milestones, and success metrics, particularly when initiatives begin with limited documentation or clearly defined scope.
Develop and maintain project, risk, and communication plans that keep initiatives organized and moving forward.
Facilitate project kickoffs, working sessions, status reviews to maintain alignment and momentum.
Translate business objectives into actionable project plans and coordinate effectively across business and technology teams.
Manage competing priorities across multiple initiatives while maintaining focus on deadlines and deliverables.
Serve as the central point of coordination for project stakeholders across business, operations, and technology teams.
Navigate complex stakeholder environments, aligning leaders with differing priorities and ensuring timely decisions.
Provide clear and consistent updates to leadership and key stakeholders.
Proactively resolve bottlenecks and drive decision-making by ensuring leaders have the information needed to move initiatives forward.
Identify project risks and issues early and implement mitigation strategies to prevent delays.
Escalate critical risks, decisions, or stalled workstreams to appropriate leadership forums.
Adapt project plans as requirements evolve while maintaining focus on core objectives.
Conduct project reviews and capture lessons learned to support continuous improvement.
Work collaboratively with colleagues to ensure consistent project management practices across initiatives.
Assist colleagues or step in across projects when necessary to maintain continuity and progress.
Identify and implement opportunities to improve project delivery processes, tools, and operating models.

Benefits

Medical (including prescription coverage)
Dental
Vision
Health Savings Account
Commuter Account
Health Care and Dependent Care Flexible Spending Accounts
Group Accident
Group Critical Illness
Life Insurance
AD&D
Group Legal
Identify Theft Protection
Wellbeing Program and Work/Life Resources (including Employee Assistance Program)
Paid Holidays
Annual Paid Time Off (includes paid state/local paid leave where required)
Short-Term Disability
Long-Term Disability
Other Leaves (e.g., Bereavement, FMLA, ADA, Jury Duty, Military Leave, and Parental and Adoption Leave)
Contributory Pension Plan and Savings Plan (401k)