Sr. Project Manager

Want to be a bswifter? At bswift we’ve been transforming benefits administration since 1996, making it simpler, smarter, and more human. Our state-of-the-art, cloud-based technology and services empower employees to understand, manage, and love their benefits. From downtown Chicago, and remotely across the country, we serve thousands of companies and millions of people nationwide, reducing administrative burdens and freeing HR teams to focus on creating thriving, people-first workplaces. We’re looking for motivated and goal-driven individuals who share our passion for delivering excellence and creating solutions that make a difference. The reward is a fun, flexible and creative environment with ample opportunity for professional and personal growth. If you love the bswift values of pursue excellence, embrace accountability, deliver superior service, and be a great place to work, we want to hear from you! WHAT YOU’LL DO (Job Summary) Support the Enterprise Project Management Organization (EPMO) by driving client‑facing benefits administration initiatives as well as enterprise‑level internal programs . This role requires a strong understanding of benefits administration products , hands‑on experience servicing clients , and leading projects tied to service delivery, operational readiness, and annual enrollment (AE) . You will partner closely with client service, implementation, product, and technology teams to ensure high‑quality execution and client satisfaction. The Senior Project Manager will advance organizational strategy, improve operational efficiency, and ensure consistent, high‑quality project delivery across a diverse portfolio of client and internal initiatives. WHAT YOU WILL BE RESPONSIBLE FOR (Essential Functions) 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 internal stakeholders. Drive projects related to client service delivery, benefits platform enhancements, operational readiness, and annual enrollment planning and execution . Serve as a trusted partner to client service teams by proactively identifying risks, managing dependencies, and resolving issues that may impact client experience or delivery timelines. Ensure client initiatives align with goals related to client health, satisfaction, retention, and long‑term partnership success . Annual Enrollment (AE) & Service Delivery Initiatives Lead or support annual enrollment–related projects , including planning, cross‑team coordination, readiness tracking, and post‑AE analysis. Coordinate efforts across service delivery, technology, product, and operations teams to ensure smooth execution during high‑volume, time‑sensitive benefit cycles. Apply strong organizational and communication skills to manage competing priorities and mitigate risk during peak enrollment periods. Internal Strategic & Enterprise Program Leadership Manage internal initiatives that directly support client success, service model improvements, and benefits administration operational efficiency . Oversee enterprise programs such as technology implementations, process optimization, and enhancements to benefits administration tools and workflows. Champion continuous improvement and innovation to streamline delivery, reduce manual effort, and improve scalability. Integrated Project Management & Governance Develop, maintain, and execute detailed project plans using Smartsheet as a primary tool, along with Jira and other project management platforms as needed. Apply Agile, Scrum, or Waterfall methodologies appropriately based on project scope and client needs. Facilitate collaboration across cross‑functional internal teams, external vendors, and executive stakeholders. Track and manage timelines, budgets, risks, issues, and dependencies to ensure successful delivery. Communicate project status, milestones, risks, and outcomes clearly and consistently to stakeholders at all levels. WHAT YOU NEED TO SUCCEED (Required Education & Experience) Bachelor’s degree required; advanced degree preferred. 5–10 years of experience in benefits administration products and platforms , preferably in a client‑facing or service delivery environment. Demonstrated experience servicing clients and leading client‑driven initiatives in a benefits administration or benefits technology setting. 2–5 years of direct project or program management experience , managing complex, cross‑functional 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. Ability to work independently in a remote environment while managing multiple priorities. NICE TO HAVE (Preferred Education & Experience) PMP certification preferred. Experience leading or supporting annual enrollment projects at scale. Background in benefits technology, consulting, or SaaS environments. Experience driving enterprise‑level change or large‑scale operational improvement initiatives. Why Join bswift? At bswift, we empower our employees to make a meaningful impact, innovate, and grow. Joining our team means stepping into a collaborative and dynamic environment that values creativity, initiative, and a passion for client success. We are dedicated to fostering an inclusive workplace that celebrates diversity and values each team member’s unique contributions. Benefits of Working at bswift: Comprehensive Health Benefits : Access to health, dental, and vision plans to support your wellness and that of your family. Competitive Compensation : A compensation package that recognizes your skills, experience, and contributions, including performance-based incentives for most roles. Remote first, Office friendly environment! No time to commute? No problem! Retirement Savings Plans : Options to help you plan for a secure financial future with employer-sponsored retirement savings programs. Professional Development : Opportunities for career growth, including training and access to resources to support your career progression. Supportive Culture : A work environment that encourages collaboration, open communication, and creative problem-solving, where your voice and ideas are valued. Employee Wellbeing Initiatives : Programs focused on mental health, financial planning, and wellness resources to help you thrive inside and outside of work. Make an Impact : At bswift, your work directly contributes to transforming how organizations approach benefits administration and client engagement. Join us to be part of an organization that is making a meaningful difference in the lives of our clients and their employees. Specific benefit offerings vary by position and may be subject to change. Standard working hours are 8am-5pm Central Time, unless otherwise stated in the Job Description. In the spirit of pay transparency, we are excited to share the base salary range for this position is $110,000-$135,000, exclusive of fringe benefits or potential bonuses. If you are hired at bswift, your final base salary compensation will be determined based on factors such as geographic location, skills, education, and/or experience. In addition to those factors – we believe in the importance of pay equity and consider internal equity of our current team members as a part of any final offer. Please keep in mind that the range mentioned above is the full base salary range for the role. Hiring at the maximum of the range would not be typical in order to allow for future & continued salary growth. We also offer a generous compensation and benefits package! At bswift, our mission is clear: Become the preeminent benefits administrator through exceptional people, innovative technology, and delighted customers. And our values are at the heart of everything we do to accomplish that mission. We Pursue Excellence, Embrace Accountability, Deliver Superior Service, and strive to Be A Great Place To Work . We take pride in having an engaged, collaborative team that goes the extra mile to get the job done right. bswift has been regularly named one of Chicago’s Best and Brightest Companies to Work For®, as well as one of the Nation’s Best and Brightest Companies to Work For® year after year. We offer a fun, flexible, and creative environment where you can grow both professionally and personally. If you have what it takes to join our award-winning culture, we’d love to hear from you!