Vice President, Engineering

Direct Supply•Milwaukee, WI

About The Position

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.

Requirements

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
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.

Nice To Haves

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

Responsibilities

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.