Direct Management Jobs in Brookfield, 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 Senior Director, Product Management - Spend Management position, you'll define and lead the product strategy, vision, and execution for Direct Supply's Spend Management platform, delivering innovative procurement and spend intelligence solutions that help senior living and healthcare providers improve operational and financial performance. You'll own the end-to-end product portfolio, driving AI-enabled innovation, expanding strategic platform capabilities, and accelerating customer adoption through data-informed decision making. As the senior product leader for the solution group, you'll lead a team of Product Managers and partner closely with Engineering, Sales, Customer Success, and executive leadership to deliver scalable, customer-centric products that fuel growth, retention, and measurable business impact. This role reports solid line to the General Manager of Spend Management and dotted line to the Corporate Vice President of Product Management.

• Builds & Drives Strategy - Develops and leads a clear, forward-looking, AI-powered product strategy and roadmap. Secures alignment across senior leaders and teams, translating long-term vision into measurable priorities and disciplined execution.

• Ensures a Customer Focus - Keeps our customer needs at the center; Tirelessly pushes for AI-First solutions to create customer value. Taps into market and customer insights to shape priorities and make decisions.

• Leverages AI & Business Insight - Leads with an AI-First mindset infusing technology into customer solutions and workflows. Harnesses the power of AI and data to cut through noise and inform decisions. Blends business savvy, financial acumen, industry knowledge, and tech expertise to set priorities.

• Demonstrates Executive Presence - Ignites enthusiasm and inspires trust and confidence. Effortlessly captivates customers and Executives. Exudes a commanding presence while keeping cool and staying humble.

• Proven ability to scale a SaaS platform with measurable adoption and feature utilization goals, driving deep customer engagement and retention.

• Strong commercial and monetization expertise, including experience with transaction-based revenue models, marketplace economics, supplier-funded programs, or data-driven revenue streams.

• Demonstrated ability to lead cross-functional accountability across Product and Engineering, ensuring reliable delivery against roadmap commitments and performance targets.

• Deep experience building data-driven platforms that ingest, normalize, and generate insights from complex operational datasets.

*Click here for a full list of DS 2.0 Leader skills and definitions.*

• Define and lead the multi-year product strategy for a cloud-based procurement and spend management platform that combines eCommerce ordering, analytics, benchmarking, and advisory-enabled services, shaping how Direct Supply competes in the healthcare procurement technology market

• Drive measurable adoption and utilization across core platform capabilities, ensuring the product organization delivers revenue growth, margin impact, and clear customer ROI through automation and spend optimization

• Strengthen the platform's commercial model, including transaction-based revenue, supplier fee structures, and value-based service offerings, to achieve revenue and margin targets

• Lead the development of the platform's spend data capabilities by integrating data from multiple systems (AP, purchasing, p-card, and external feeds), standardizing it, benchmarking performance, and using AI to generate practical, actionable insights

• Embed AI capabilities into core workflows - including predictive forecasting, anomaly detection, supplier performance analysis, and automated decision support - to differentiate the platform in the healthcare market

• Partner closely with Engineering leadership to ensure high delivery reliability, scalable architecture, and disciplined execution against roadmap commitments

• Design interoperable product capabilities that connect procurement workflows, clinical cost insights, and operational data within a cohesive ecosystem

• Align product capabilities with strategic supplier and enterprise partnerships, ensuring integrations, data exchange, and co-developed services drive mutual growth

• Lead the development and launch of adjacent product extensions that expand the platform's capabilities and revenue contribution

• Establish clear product success metrics tied to adoption, retention, customer ROI, revenue growth, and margin performance

• Directly lead, develop and mentor a high-performing team of Product Managers, building strong discovery practices, outcome-based roadmapping, and data-driven decision making

• Serve as the executive voice of the Spend Management portfolio, engaging customers, supplier partners, and procurement industry stakeholders to represent platform strategy and reinforce Direct Supply's position as a leader in AI-enabled spend management

• Bachelor's degree required; MBA or advanced degree preferred

• 15+ years of product management experience, including senior leadership roles within SaaS, marketplace, procurement technology, supply chain technology, fintech, or data platforms

• Experience scaling a transaction-based or marketplace-style platform with measurable revenue and margin accountability

• Proven success building products that leverage AI and advanced analytics to create differentiated customer value

• Demonstrated experience leading Product Managers and partnering closely with Engineering to deliver complex, data-intensive platforms

• Strong executive communication skills with the ability to influence senior stakeholders and represent product strategy externally

• Ability to travel by car and/or plane up to 25%

• Valid, unexpired driver's license with satisfactory driving record

• Experience in healthcare, senior living, supply chain, procurement, or spend analytics markets

• Background in data platforms that unify multiple operational systems into a single intelligence layer

• Experience integrating software platforms with professional or advisory service offerings

Job to be performed in the location listed. Generous benefit package available.

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