Senior Program 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!  

About the role

Business results are the job. Program and project management are the tools. As a Program Manager, Business Solutions, you'll own outcomes across our health and welfare benefits administration business: revenue, retention, cost, scale, and client satisfaction. You'll use whatever combination of planning, execution, influence, and hands-on work it takes to deliver them. AI is part of that toolkit, not a side project.

What you'll own

A portfolio of high-stakes programs tied to financial and operational outcomes: revenue generation, cost optimization, client retention, and platform scale.

The business result. You'll build and manage timelines, milestones, and deliverables. You'll change the plan when that's what hits the result.

Executive communication on how your programs are performing, what's at risk, and what the business should do about it.

Cross-functional execution across Product, Technology, Service Delivery, Operations, and Finance.

Hands-on problem solving when the outcome demands it. You build solutions yourself rather than wait, whether that's standing up an AI agent, designing a new process, or stepping into adjacent work outside your lane.

Operational and process improvement across how benefits are delivered at scale.

How you'll operate

The Program Managers who thrive here share a few common habits:

Lead with the business result.  Revenue, retention, cost, scale, and client satisfaction are the language of this role.

Own what you don't own.  Look across the silos and push for action when no one else is. Get names, commitments, and follow-ups.

Look around corners.  Anticipate what's coming before it arrives. Bring a recommendation, not just a problem.

Use AI as a force multiplier.  Build agents, skills, and automation into how you work. The expectation is more impact, not more hours.

Make the news.  Bring ideas even when you're not the SME. Keep asking questions until things make sense.

Roll with the pace.  Direction shifts fast here. Expect feedback, iteration, and the occasional restart.

What you bring

Required:

8+ years of direct experience in health and welfare benefits administration. Operations, client delivery, or implementation inside a benefits admin platform, TPA, or carrier. 

A track record of owning business outcomes such as revenue, cost, retention, and performance metrics.

Experience leading complex programs that span multiple projects, stakeholders, and functions.

Demonstrated ability to influence cross-functional teams without direct authority.

Direct exposure to executive audiences. You've presented to senior leadership and held the room.

Strong financial acumen and a working partnership with Finance.

Fluent, daily use of AI in your work. You already build or use agents, custom skills, and automations to accelerate analysis, communication, and execution. You stay current on what's new and adopt it fast.

Strongly preferred:

A history of being trusted with the hardest accounts or most visible programs.

Fluency moving between strategy and execution. Comfortable in front of an executive and equally comfortable getting into the weeds.

Fluency with carrier feeds, OE cycles, COBRA, ACA reporting, eligibility, and the operational complexity of delivering benefits at scale.

Sharp written communication.

Education:  Bachelor's degree or equivalent industry experience. Deep, hands-on experience in benefits administration will be weighed at least as heavily as formal education.

What success looks like in year one

The programs you touch deliver the business result, and executives can describe what you own and why it matters without you in the room.

Cross-functional partners across Product, Technology, Service Delivery, and Finance tell us you made them better, sharper, or faster.  

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!