Program Strategy Manager Jobs in Milwaukee, WI (NOW HIRING)

Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. In the Program Manager, Spend Management position, you’ll lead the design and execution of high-impact programs that drive innovation and scale across Spend Management. You’ll formalize how teams explore, pilot, and operationalize new ideas, creating structure around intake, execution, and governance. Partnering across product, technology, operations, and customer success, you’ll coordinate cross-functional efforts to turn strategic concepts into scalable outcomes.

Deals with Ambiguity – Adapts smoothly to change and thrives in ambiguity, maintaining composure and productivity. Maintains progress despite incomplete information and tackles complex issues constructively. Communicates Effectively – Develops and delivers impactful communications for diverse audiences across channels. Excels in both small and large group interactions. Captures attention, actively listens, and guides discussions towards targeted goals. Champions Innovation – Propels teams to unlock value with cutting-edge, tech-enabled innovations. Stays ahead of the tech curve, ready to embrace the next big thing. Leads with an entrepreneurial mindset and takes calculated risks. Collaborates Effectively – Forges strong partnerships and works productively with others to achieve common goals. Finds common ground to solve problems and seeks out diverse perspectives to inform decisions. Quickly earns trust, puts others at ease, and shows empathy. Strong program management expertise with a proven ability to lead complex, cross-functional initiatives from concept to execution. Deep fluency in agile and OKR frameworks to drive transparency, alignment, and measurable outcomes. Skilled at influencing without authority, guiding prioritization, governance, and resource planning across teams.

Design and implement scalable program structures for intake, governance, stage-gating, and reporting. Collaborate with leadership to define and evolve the program lifecycle. Drive discovery and alignment on scope, timelines, and objectives for new programs. Develop frameworks and materials that guide prioritization, decision-making, and resource allocation. Lead cross-functional pilot execution and scale-up decisions. Leverage OKRs and agile principles to track progress and increase visibility. Analyze program data to inform decisions, surface risks, and weigh tradeoffs. Serve as program lead for strategic initiatives, ensuring delivery of key milestones and outcomes. Build alignment and collaboration across Product, Technology, Engineering, Operations, Marketing, and Success teams. Contribute to strategic planning and roadmap development with Spend Management leadership. Champion an AI-and automation-first mindset across all programs and processes.

• Bachelor’s degree in Business, Technology, Operations, or a related field
• 7+ years of experience leading cross-functional programs, ideally in tech, operations, or platform-based environments
• Strong knowledge of agile, OKRs, and strategic planning frameworks
• Proven success designing pilots and scaling initiatives across internal and external teams
• Effective communicator with strong facilitation and organizational skills
• Experience supporting supplier- and customer-facing initiatives

• PMP, Agile, or other program management certification preferred.
• Background in supplier networks, digital platforms, or spend analytics a plus.

Job to be performed in the location listed.

Generous benefit package available.

© 2013 to 2026 Direct Supply, Inc. All rights reserved. Direct Supply delivers solution-driven platforms, products and services to help solve the toughest challenges facing Senior Living and Healthcare. For more than 35 years, we’ve grown consistently while expanding our offering of innovative solutions for virtually every critical area of senior health across the continuum of care. If you asked our 1,200+ Partners what separates Direct Supply from other applied technology companies, it’s that we are 100% employee owned and driven to work with a purpose. Every day, we strive to honor our mission of enhancing the lives of millions of seniors and healthcare professionals in a results-oriented agile environment that gives our Partners the necessary tools and flexibility to truly bring what’s next to Healthcare. Ready to make a difference?