Assistant Vice President Jobs in Milwaukee, WI
Assistant Vice President jobs in Milwaukee are concentrated in the Third Ward, Downtown, and the Financial District, with strong demand across banking, insurance, and healthcare from employers like WSP, UMOS, and Fiserv. Hiring activity remains steady as organizations build out their leadership pipelines in these sectors. Scan the live roles below and apply to whichever ones fit.
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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.
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.
© 2013 to 2026 Direct Supply, Inc. All rights reserved.
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.
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.
© 2013 to 2026 Direct Supply, Inc. All rights reserved.
See All 47 Assistant Vice President Jobs in Milwaukee
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Who's Hiring
Assistant Vice President Jobs in Milwaukee: Frequently Asked Questions
How do I get a assistant vice president job in Milwaukee?
Focus your search on Milwaukee's financial services corridor downtown and the insurance and healthcare organizations headquartered along the lakefront and in the Third Ward. Candidates who stand out typically combine a relevant bachelor's degree with five or more years of functional experience in operations, finance, or strategy. Relationships built through local professional associations and Milwaukee-area business networks also give applicants a meaningful edge over outside candidates.
Which companies hire assistant vice presidents in Milwaukee?
Companies currently hiring assistant vice presidents in Milwaukee include WSP, UMOS, and Fiserv, per current listings on Migrate Mate as of November 2026. Milwaukee's base of regional banks, national insurers, and large healthcare systems makes it one of the more active Midwestern markets for this level of leadership hire.
Are there remote assistant vice president jobs in Milwaukee?
Yes, though availability depends heavily on function. Assistant vice president roles in strategy, finance, and analytics tend to support remote or hybrid arrangements, while those tied to branch operations or client-facing teams are almost always on-site. About 50% of assistant vice president openings tied to Milwaukee are remote or hybrid as of November 2026, with the most flexibility found in corporate functions rather than line-of-business leadership.
How can I get a assistant vice president job in Milwaukee with little or no experience?
The most realistic entry path in Milwaukee is moving up through associate or senior analyst roles at one of the city's regional banks or insurance carriers, where internal promotion to assistant vice president is a structured and common step. Milwaukee employers like mid-sized financial institutions and large healthcare organizations regularly develop talent from within, so lateral moves into high-visibility project or operations roles can accelerate the timeline. Demonstrating ownership of a team, budget, or cross-functional initiative is the clearest signal hiring managers look for locally.
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See All 47 Assistant Vice President Jobs in Milwaukee
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