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Vice President, Engineering

Direct Supply · Milwaukee, WI · Full time

Posted Aug 12, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you institutionalized engineering standards across many teams. How did you get adoption without slowing delivery?

What they are checking: Ability to create shared architecture, data and design standards that teams actually follow.

How do you develop engineering leaders who report to you so they can run their areas without you?

What they are checking: Leadership depth in growing managers, which the posting places at the center of the role.

Tell me about a major technical bet you made that did not pay off. What did you learn?

What they are checking: Honest reflection on risk-taking, which matters for a leader championing innovation.

How do you build an engineering culture that values both technical excellence and the people it serves?

What they are checking: Whether they can connect engineering culture to the mission of improving lives for seniors and caregivers.

What would you do

You join and find each product team built its own stack and practices. What do you do first?

What they are checking: Judgment on when to standardize and when to leave teams alone during a transformation.

How do you keep a start-up mindset and execution speed inside an established company?

What they are checking: Ability to remove friction and drive urgency without creating chaos, as the posting asks.

How do you partner with product and business leaders when engineering capacity cannot meet every request?

What they are checking: Ability to make and explain trade-offs at the executive level.

About the work

As the top engineering leader, how would you build an AI-first technology strategy for a portfolio of senior living products?

What they are checking: Whether they can set a portfolio-wide strategy that ties AI to real customer and business value.

What metrics would you use to know whether engineering is delivering well at scale?

What they are checking: A balanced view of speed, quality, reliability and value rather than a single vanity metric.

How have you used OKRs to focus an engineering organization, and where did they go wrong?

What they are checking: Practical experience with OKRs, including their failure modes, since the posting names them.

How would you change engineering practices and roles as AI coding tools become part of everyday work?

What they are checking: A considered view of how AI reshapes engineering work, culture and hiring.

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The full job description

As published by Direct Supply.

Position Summary: Direct Supply is building the future of healthcare technology across the senior living industry with market-defining products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. In the Vice President, Engineering position, you’ll serve as the top engineering leader across Direct Supply, driving enterprise-wide engineering strategy, culture, and execution. You’ll lead and develop a high-performing team of engineering leaders across the portfolio to scale our AI-first platforms, foster technical excellence, and accelerate product innovation. With a start-up mindset and deep technology acumen, you’ll shape the future of our engineering organization to enable transformative growth, execution speed, and value delivery. Skills Needed: • Builds & Drives Strategy – Crafts a visionary, AI powered, market leading DS 2.0 technology strategy and institutionalizes a scaled, disciplined software engineering discipline across our portfolio. • Focused Execution – Establishes engineering standards across architecture, data and design principles with clear metrics to drive scaled software delivery, support and lifecycle management. Sharpens the Function's OKRs for laser-focused execution of strategic goals. • Champions Innovation – Propels teams to unlock value with cutting-edge, tech-enabled innovations. Stays ahead of the tech curve, ready to embrace the next big thing. Leads with an entrepreneurial mindset and takes calculated risks. Disrupts the status quo when required while bringing the team along for the journey. • Leads Through Change & Ambiguity – Navigates the unknown with confidence, steering through change and uncertainty with a clear vision and unwavering determination. Turns chaos into clarity, keeping goals firmly in sight. • Leads & Inspires Partner Owners – Ignites Partner Owners’ passion and purpose. Boosts Partners to peak performance while operating at the top of their license. Attracts and develops top talent and builds an environment that fuels innovation. • Exceptional ability to lead complex technology organizations through rapid change, aligning technical vision with enterprise strategy. • Proven track record of scaling engineering teams in high-growth or start-up environments, balancing innovation with execution. • Expertise in building AI-first platforms and embedding emerging technologies to deliver enterprise impact. • Strong executive communication and cross-functional collaboration skills , with the ability to inspire action and gain alignment at all levels. What You’ll Do and Impact: • Lead the enterprise-wide Engineering function, setting the vision and operating model to drive AI-first product development and platform innovation. • Manage, mentor, and develop a team of engineering leaders across Solution Groups, fostering a culture of ownership, experimentation, and continuous improvement. • Shape technical strategy in partnership with Product, Architecture, and Platform leaders to deliver reliable, scalable, and secure solutions. • Drive operational excellence, ensuring high-quality execution across all engineering teams and delivering customer-centric outcomes. • Champion modern engineering practices and organizational agility to accelerate time-to-market and value delivery. • Collaborate closely with Executive leadership to ensure engineering investments align to strategic business outcomes. • Model innovation leadership by exploring new tools, AI capabilities, and startup-like models to spark engineering transformation. Experience: • Bachelor’s degree in Computer Science, Engineering, or related field; Master’s degree preferred • 15+ years of software engineering and architecture experience • 10+ years of progressive people leadership, including senior technical leaders across multiple teams or departments • Proven success leading large-scale engineering organizations and building AI-first platforms • Experience in high-growth or start-up environments preferred • Deep understanding of software development lifecycle, cloud-native architectures, and modern engineering practices Additional Items of Interest: • AI, architecture, or cloud certifications strongly preferred • Experience working in regulated, enterprise, or multi-product technology environments • Demonstrated thought leadership in engineering, AI, or product development Job to be performed in the location listed. Generous benefit package available. © 2013 to 2026 Direct Supply, Inc. All rights reserved.

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