General Manager and Vice President, DSSI

Direct Supply, Inc.; Milwaukee (WI); On-site; USD 250,000 - 400,000; Full time

Benefits offered by this job

Generous benefit package

Job summary

Direct Supply, Inc. seeks a seasoned leader to build and execute the DSSI business strategy, shaping a portfolio of products, platforms, and services.

You will drive financial performance, partner with Engineering, Sales, Marketing, and Operations, and guide AI-enabled initiatives that create customer value in senior living and healthcare markets. The role emphasizes cross-functional leadership and strategic execution.

Qualifications

• Bachelor's degree in Business, Technology, Product Management, or related field; advanced degree preferred.
• Significant leadership experience (15+ years) in a technology-enabled business with accountability for strategy, product direction, and financials.
• Proven strategic judgment to synthesize market and tech insights and decide where to invest.

Responsibilities

• Build and lead DSSI's business strategy using market, competitive, and economic insights.
• Shape DSSI's role within the Solution Group portfolio and integrate with other Direct Supply offerings.
• Set product, platform, and services strategy and lead PM in translating strategy into a portfolio and roadmap.
• Own DSSI's business plan and financial performance, including revenue and investment performance.
• Lead development and commercialization of new products, services, and AI-enabled capabilities.
• Build relationships with customers, suppliers, and partners across functions to deliver strategy.
• Develop a high-performing leadership team and evolve the organization and operating model.

Skills

Strategic leadership

Product strategy

Financial acumen

AI fluency

Cross-functional collaboration

Education

Bachelor's degree in Business/Technology/related field

Advanced degree preferred

Job description

What You’ll Do and Impact:

Build and lead DSSI's business strategy using customer, market, competitive, technology, and economic insight; make clear choices about where to play, how to win, and where to invest. Shape DSSI's role within the broader Solution Group portfolio and identify opportunities to integrate DSSI with other Direct Supply and industry solutions. Use open, interoperable approaches to connect products, services, data, technology, and capabilities, creating greater customer value and bringing DSSI insights forward to influence broader priorities. Set DSSI's product, platform, and services strategy and lead Product Management in translating strategic choices into a focused portfolio and roadmap, including decisions about what to build, buy, or partner for. Own DSSI's business plan and financial performance, including revenue, contribution margin, operating expenses, and investment performance; understand the economic drivers of the business and make informed trade-offs among growth, customer value, innovation, and profitability. Establish and lead a disciplined operating cadence that connects strategy, product and service priorities, financial commitments, and execution; use clear measures to assess performance, surface risks and opportunities, adjust priorities, and drive accountability. Lead the development and commercialization of new products, services, and business models, including AI-enabled capabilities, from opportunity and business case through launch, adoption, and ongoing performance. Build deep relationships with customers, suppliers, and strategic partners, and partner across Engineering, Applied AI, Sales, Marketing, Operations, and Finance to mobilize the capabilities needed to deliver DSSI's strategy. Build and develop a high-performing DSSI leadership team, strengthen talent and succession, and evolve the organization, operating model, and use of AI and automation as the business changes. Work with senior leadership team to align DSSI's priorities and resources with Direct Supply's broader goals and lead changes that support business performance.

What You'll Bring:

Bachelor's degree in Business, Technology, Product Management, or a related field, or equivalent relevant experience; advanced degree preferred. Significant leadership experience (15+ years) in a technology-enabled business, platform, product portfolio, or services business, with demonstrated accountability for strategy, product direction, financial performance, and measurable business outcomes. Proven strategic judgment: the ability to synthesize customer, market, competitive, technology, and economic insight; make clear choices about where to play, how to win, and where to invest; and position a business effectively within a broader portfolio. Deep product, platform, and services leadership experience, including shaping portfolios and bringing technology-enabled offerings from customer need and business case through launch, adoption, and ongoing performance. Strong business and financial acumen, with experience understanding business economics, managing performance, allocating resources, and making consequential trade-offs across growth, customer value, investment, and profitability. Demonstrated ability to turn strategy into execution - establishing goals and operating rhythms, leading through shared capabilities and matrixed teams, resolving trade-offs, and holding leaders accountable for results. Track record of building strong leaders and organizational capability, influencing senior stakeholders, and navigating complexity and change with sound judgment and an enterprise mindset. Curiosity and fluency with AI, data, and emerging technologies, with experience applying them to create customer value, evolve products or services, or improve how work gets done. Experience in healthcare, senior living, or other complex business to business technology markets. Experience commercializing AI-enabled products, SaaS platforms, data products or partner-based offerings. Experience with strategic partnerships, licensing, or launching new revenue programs. Job to be performed in the location listed.

Generous benefit package available.

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?