General Manager and Vice President, DSSI

Direct Supply; Milwaukee (WI); On-site; USD 260,000 - 380,000; Full time

Benefits offered by this job

Generous benefits package

Job summary

Direct Supply is building the future of healthcare technology with leadership in products, platforms, and services. The General Manager and VP of DSSI shapes strategy, portfolio, and execution to deliver differentiated customer value and sustainable growth.

The role leads Product Management, drives investment decisions, and aligns resources with Direct Supply's goals, including AI-enabled capabilities and data-driven decision making.

Qualifications

• Bachelor's degree in Business, Technology, Product Management, or related field; advanced degree preferred.
• 15+ years of leadership in a tech-enabled business, with accountability for strategy and financial performance.
• Strong strategic judgment to synthesize market, technology, and economic insight; clear portfolio positioning.
• Deep product, platform, and services leadership experience from discovery to launch and ongoing performance.
• Strong business and financial acumen with experience managing performance and resource allocation.
• Proven ability to translate strategy into execution with disciplined operating rhythms.

Responsibilities

• Build and lead DSSI's business strategy using customer, market, and economic insights.
• Shape DSSI's role within the Solution Group and integrate with other Direct Supply capabilities.
• Lead Product Management to translate strategy into a focused portfolio and roadmap.
• Own DSSI's business plan and financial performance, balancing growth and profitability.
• Establish an operating cadence to connect strategy, priorities, and execution; monitor risks and opportunities.
• Lead development and commercialization of AI-enabled products, from opportunity to adoption.

Skills

Strategic leadership

Product management

AI familiarity

Healthcare domain

Financial acumen

Stakeholder management

Enterprise mindset

Education

Bachelor's degree

Advanced degree preferred

Job description

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.

The General Manager and Vice President, DSSI leads the strategy, product and services portfolio, business performance, and ongoing evolution of one of Direct Supply's core technology platforms. This role is responsible for positioning DSSI to deliver differentiated customer value, strengthen its competitive position, and drive sustainable, profitable growth.

As part of the broader Solution Group, you'll shape DSSI's strategic direction and identify opportunities to connect solutions, capabilities, investments, data, technology, and customer relationships to create greater value. You'll translate these strategic priorities into product and service direction, investment decisions, financial commitments, and disciplined execution.

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.

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