Gil Shklarski is a former CTO-operator who scaled Flatiron Health's engineering team from 2 people to 350 through Roche's acquisition, bringing an unusually diverse background spanning elite Israeli Defense Forces tech units, a PhD, and engineering roles at Microsoft and Facebook. He's known for creating the "Xanax for Decision-Making" framework—a widely-referenced decision matrix that helps scaling teams categorize choices and maintain autonomy—and for advocating an "opportunistically lazy" engineering culture where people automate themselves out of their current jobs to tackle harder problems. Gil Shklarski is a former CTO-operator who scaled Flatiron Health's engineering team from 2 people to 350 through Roche's acquisition, bringing an unusually diverse background spanning elite Israeli Defense Forces tech units, a PhD, and engineering roles at Microsoft and Facebook. He's known for creating the "Xanax for Decision-Making" framework—a widely-referenced decision matrix that helps scaling teams categorize choices and maintain autonomy—and for advocating an "opportunistically lazy" engineering culture where people automate themselves out of their current jobs to tackle harder problems.