I’m Craig Bennett. I lead large engineering organizations in infrastructure, data, platform, and AI. I specialize in making them work when they’re broken.
Most recently I was Senior Director of Engineering at NerdWallet, where I oversaw roughly half of the company’s engineering capacity: cloud infrastructure, platform services, data engineering, business intelligence, and QA. That was about 100 engineers, 11 teams, and a $36M budget at a public company doing $800M+ in revenue. I defined and drove the company’s AI engineering strategy, including company-wide adoption of AI-assisted development tools, internal AI agents that replaced manual infrastructure workflows, and an AI culture program with external speakers and regular demo sessions that positioned engineering as the leading voice on AI inside the company.
Before NerdWallet, I was at Amazon, where my teams owned the data engineering, knowledge graph, and infrastructure behind one of Alexa’s highest-volume knowledge engines. These were systems that served millions of users daily and had to be right at scale.
The thread that runs through my career is fixing things that are broken. I’ve led three organizational turnarounds, inheriting teams with collapsed morale, stalled delivery, or failed leadership, and restored them to high function while retaining the people who mattered. I think of organizational repair as a discipline, not a crisis response.
Before I was an engineering leader, I was a scientist. I have a PhD in Cognitive Neuroscience from Dartmouth, where I studied human brain development, and I spent four years as a postdoctoral researcher at UC Santa Barbara investigating human memory and decision-making using fMRI. That research still shapes how I think about organizations: how people process information under uncertainty, how teams make decisions, and why the dynamics inside a company are often more determinative than the technology it builds. You can explore that earlier body of work at prefrontal.org.
I’m currently pursuing my MBA at UCLA Anderson, and I write about engineering leadership, AI strategy, and technology management here on this blog.
Elsewhere
LinkedIn | Professional background and connections
My Leadership Operating Manual | My manager README: operating principles, expectations, and what it’s like to work with me
Bluesky | Shorter-form updates and observations