Derek Mogar is an architect at LeanScale, where he leads quote-to-cash and CPQ transformations for B2B SaaS companies. He came up in sales — his father spent a whole career in enterprise sales — and now works in the machinery of how companies configure, quote, bill and recognise revenue, specialising in colliding product-led and sales-led motions, co-termed expansions, ramp deals and rip-and-replace contracts. On the engagement featured in episode 108 he built a production-grade CPQ inside HubSpot using Claude Code in two days, replacing a $60K platform the customer had spent two months evaluating.
“Oh these are nice to have automation so that way we can not have to do as much work.”
“if we don't do this it could put deals at risk, if billing looks funky it could put our reputation at risk”
“Not gonna call it a love story but it was a love at first sight when they saw it.”
“They loved it immediately and they're basically just said well why don't we just use this”
“it was kind of just a wild wild west from what you can see in the data”
“it was almost like a one-trick pony. You can put a product in there. You can select a quantity.”
“it's driving how your contracts are laid out, how your proposals are laid out, your commission systems, your forecasting.”
“it creates repeatable, confident, stable, structured data”