Senior Technology Product Manager

Direct Supply, Inc.; Milwaukee (WI); On-site; USD 110,000 - 140,000; Full time

Job summary

Direct Supply, Inc. is seeking a Senior Technology Product Manager in Milwaukee to lead the vision, strategy, and roadmap for frontline technology products.

You will align product development with customer needs, market trends, and financial outcomes, driving innovation, adoption, and growth in collaboration with data and engineering teams. You will partner with finance, product owners, and senior leadership to ensure backlog clarity, measure success, and steer investments toward high-impact

Qualifications

• Bachelor’s degree in Business, CS, or related field.
• MBA or equivalent preferred.
• 5+ years of product management experience with increasing responsibility.
• Experience with AI-enabled features, analytics tools, and product experimentation methods.

Responsibilities

• Own the strategic direction and roadmap for 1–3 technology products or capabilities.
• Lead customer discovery and validation sessions to surface needs and test assumptions.
• Develop and refine product strategies based on data, market trends, and operations.
• Report quarterly on market conditions, competitor shifts, and opportunities.
• Align products with OKRs in collaboration with tech leadership and senior stakeholders.
• Drive AI-enhanced feature development with engineering and data science teams.
• Lead product experiments and translate insights into roadmap evolution.
• Define and track metrics like adoption, engagement, and retention.
• Collaborate with Finance to evaluate profitability and budgeting.

Skills

Systems Thinking

Problem Solving

Learn & Adapt

Influence & Collaboration

AI Features Familiarity

Analytics Tools

Experimentation

Financial Modeling

ROI Evaluation

Education

Bachelor’s degree in Business, Computer Science, or related field

MBA preferred

Job description

Position Summary:

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 Senior Technology Product Manager position, you’ll lead the vision, strategy, and roadmap for one or more technology products or capabilities. You will be accountable for aligning product development with customer needs, market trends, and financial outcomes. Through ongoing experimentation, collaboration with data and engineering teams, and strategic influence across business lines, you’ll drive innovation, adoption, and product growth. You’ll serve as a visible product leader—operating at the intersection of customer insight, technical feasibility, and business impact.

Skills Needed:

• Systems Thinking & Problem Solving - Identify the right problems to solve by understanding the broader system – customers, stakeholders, processes, data, technology, and AI. Connect root causes, dependencies, tradeoffs, and upstream and downstream effects to develop practical, scalable solutions that improve the whole.
• Learn & Adapt - Continuously grow and adapt as technology, customer needs, roles, and work systems evolve. Stay curious, learn beyond your core specialty, experiment with new approaches, use AI to accelerate learning, and improve through feedback and setbacks.
• Influence & Collaborate - Build trust, communicate clearly, and work across boundaries to drive action and shared outcomes. Seek and integrate different perspectives, contribute ideas, work through dependencies, and help teams make progress together through change and ambiguity.
• Maintains expertise in market trends and competitive landscape to shape product strategy. Leverages financial insights by partnering with finance teams to evaluate product profitability, support budgeting, and guide investment decisions. Monitors and analyzes key product performance metrics, such as feature utilization and adoption rates, to enhance engagement and retention.

What You’ll Do and Impact:

• Own the strategic direction and roadmap for 1–3 technology products or capabilities
• Lead customer discovery and validation sessions to surface needs and test assumptions
• Develop and refine product strategies based on customer data, market trends, and operational realities
• Report quarterly on market conditions, competitive shifts, and product opportunities to influence org-level planning
• Align products with business strategies and OKRs in collaboration with tech leadership, GMs, and senior stakeholders
• Drive AI-enhanced feature development by partnering with engineering and data science to improve product outcomes and operational efficiency
• Lead product experiments, surface insights, and use findings to inform roadmap evolution and innovation priorities
• Define and track product success metrics such as adoption, engagement, feature utilization, and customer retention
• Identify and execute initiatives to improve product performance and user satisfaction
• Collaborate with Finance to evaluate product profitability, contribute to budgeting, and support investment decisions
• Partner closely with Product Owners to ensure backlog clarity and delivery alignment with strategic outcomes
• Represent product outcomes in leadership forums and communicate roadmap and performance to stakeholders

Experience:

• Bachelor’s degree in Business, Computer Science, or a related field (MBA preferred)
• 5+ years of experience in product management with increasing responsibility
• Proven ability to lead product strategy, experimentation, and cross-functional collaboration
• Experience with financial modeling, ROI evaluation, and business case development
• Familiarity with AI-enabled features, analytics tools, and product experimentation methods
• Ability to travel by car and/or plane up to 15%.

Additional Items of Interest:

• Experience in healthcare, SaaS, or data-centric platforms
• Training in product strategy, Lean Startup, or similar frameworks

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?