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Index/Finance/Go To Masters Show
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Darren Fay on Why Compensation Plans Are Art, Not Science

Go To Masters Show · 2026-02-06 · 35 min

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Episode notes

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 stable The Five Whys methodology: solve root causes, not surface issues that keep rearing their ugly heads Why comp plans fail when they're too complex or tied to outcomes reps can't control

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