Senior Technology Product Manager

Direct Supply•Milwaukee, WI

1d•Onsite

About The Position

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.

Requirements

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.
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

Nice To Haves

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

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 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