David Caldwell | Seasoned. Tested. Delivered.
From IT implementation to operational excellence, I bring decades of leadership to help you chart a bold path forward!
Elevating Technology
Performance to Enterprise Value
Introduced by a colleague to the SVP of Technology at a publicly traded software company, he asked me to join his team, and I walked into a crisis. Their revenue-driving data collection system was failing, the distributed engineering team was leaderless, and delivery had ground to a halt. As Director of Software Engineering, I launched an accelerated, end-to-end assessment of people, process, and technology. What I found was stark: a crumbling revenue architecture and a team surviving on brute force instead of proven practices.
Amid the chaos, I spotted one engineer with raw leadership talent and deep technical insight. Together, we retooled the team—implementing Agile, building a rigorous backlog, and prioritizing fixes and enhancements with the most significant business impact. Within 60 days, the turnaround was underway: critical issues were resolved, and executives were taking notice. After just over a year, a rebuilt, stable, compliant system rolled out to production. The CFO, once desperate, was elated—he called the turnaround “transformational”—his revenue cycle team finally had a reliable, user-friendly system that delivered.
Pioneering the Nation’s
First Digital-Driven Medical School
When Care Delivery leadership tapped me to lead technology for a flagship venture—the nation’s first medical school embedded within a healthcare system—the mandate was bold: build a digital-first medical school worthy of Kaiser Permanente’s reputation as one of the most technologically advanced healthcare organizations. This wasn’t about filling hospital rosters. The vision was to shape doctor-leaders who would elevate healthcare across the country.
Over four years, I drove this mission forward: touring top U.S. medical schools, leading architecture and technology strategy, selecting and implementing cutting-edge solutions, managing consultants, shaping curriculum, closing critical gaps, safeguarding security and risk, and embedding human-centered design into every decision. I partnered directly with executive leadership to ensure alignment and momentum.
The result: the Kaiser Permanente Bernard J. Tyson School of Medicine—built from the ground up in Pasadena, California—launched with 65+ new technologies. Despite the unprecedented disruption of COVID in 2020, the school opened on time and on budget, standing as a national model for the future of medical education.
Reinventing Healthcare
by Putting Experience First
With a track record of launching transformative ventures, I was again tapped by Care Delivery leadership to create a new consumer experience design service—a bold move to reshape Kaiser Permanente’s digital systems and elevate the entire care experience for members and patients. As experience-driven strategy became a top enterprise priority, this initiative was positioned as a revenue game-changer with direct impact on member retention and brand trust.
As product and service owner, I built the foundation from the ground up: service delivery models, intake and assessment frameworks, proposal and estimation tools, branded communications, a design learning culture, and structured collaboration channels with design partners and executives. My goal was simple but ambitious: equip design and product teams with the tools and processes to deliver repeatable, scalable success.
The results spoke for themselves. Demand for the service quickly outpaced capacity. The team was recognized for best-in-class, national award-winning service delivery, exceeding annual recharge targets by hundreds of thousands of dollars. Most importantly, experience design shifted from afterthought to enterprise focus, becoming a strategic lever that elevated Kaiser’s care delivery and deepened trust with patients and members.
Reducing Risk,
Increasing Trust—Faster
The VP of Risk Management was left reeling when his director of enterprise vulnerability governance abruptly exited—leaving behind a fractured team, weak policies, and years of stalled risk remediation. As a Business Information Security Officer hungry for a challenge, I stepped in to lead the turnaround.
Appointed interim (later permanent) director, I quickly exposed the core issue: not lack of talent, but lack of direction. Remediation was crippled by broken coordination with IT Operations and a toothless policy rife with loopholes. I immediately closed those gaps—tightening exemption policies, forging new collaboration with IT Ops leadership, and pushing through an enterprise program that tied remediation metrics directly to executive visibility and accountability. High-risk vulnerabilities could no longer hide in the shadows. The CIO raised the stakes by linking remediation targets to executive performance and compensation—governance with real consequences.
The results: in two years, Very High/High/Medium remediation surged from <55% to 88%+, DMZ risk closures jumped from 51% to 82%, and 116,000+ Very High risks and 6,300+ High risks were eliminated. We cut Break-the-Glass Very High workstation exposures by 74% and crushed Log4J from 36,479 instances to fewer than 80.
Entering my third year, the IT Operations executive praised the successes, calling it the most collaborative era the risk office had ever achieved with IT Operations. What began as a crisis became an enterprise-wide risk governance transformation—with accountability, velocity, and teeth.
