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!

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.

• 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.

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.

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…