Darren Fay on Why Compensation Plans Are Art, Not Science
Fri Feb 06 2026
Darren Fay is the VP of Operations at Littera, one of the few full-service AI-native legal software companies. On this episode of the Go To Masters Show, he shares insights from an unconventional path—starting as a firefighter where process and procedures became second nature, then leading operations across Sprint, seed-stage startups, and publicly traded companies.
Why firefighting prepared him for operations—both require following processes to keep scenes safe and stableThe Five Whys methodology: solve root causes, not surface issues that keep rearing their ugly headsWhy comp plans fail when they're too complex or tied to outcomes reps can't control
Connect with Darren: LinkedInFollow us: Linkedin | X
More
Darren Fay is the VP of Operations at Littera, one of the few full-service AI-native legal software companies. On this episode of the Go To Masters Show, he shares insights from an unconventional path—starting as a firefighter where process and procedures became second nature, then leading operations across Sprint, seed-stage startups, and publicly traded companies. Why firefighting prepared him for operations—both require following processes to keep scenes safe and stableThe Five Whys methodology: solve root causes, not surface issues that keep rearing their ugly headsWhy comp plans fail when they're too complex or tied to outcomes reps can't control Connect with Darren: LinkedInFollow us: Linkedin | X