View from the Ground: dispatches from the field.
What GTM execution actually looks like from inside a revenue team that still carries a number.
Latest
October 29, 2026From The Winding Road Show, with Cathy Highley
Claude Gets Us Answers Faster. Without a Foundation, They're the Wrong Answers.
We connected Claude to HubSpot and executives started getting different revenue numbers. Four deal revenue fields, duplicate accounts and write access that should have been read-only. AI in GTM is only as trustworthy as the data foundation underneath it.
October 18, 2026
AI Was Supposed to Build Super Reps. We Bought the Wrong Half.
Every AI sales tool works around the deal: prep before the call, notes after it. None of it touches the conversations where deals are won or lost. The half that builds better reps is coaching.
October 8, 2026From The Winding Road Show, with Brian Wagner
Most Startup Sales Leaders Aren't Bad at Ops. They Just Never Get to It.
Early-stage sales leaders used to choose between selling and running the machine. A live tracker, a coach per motion and a connected business case mean they don't have to anymore.
August 31, 2026
The First Problem Isn't the Deal. It's the Door.
Same inbound leads, same intent, wildly different conversion by rep. What separated the top converters wasn't a better close — it was refusing to stop at the first problem.
August 3, 2026
Aim Small, Miss Small. Then Know When to Ignore It.
Keep the ICP tight and the AI coach honest. Neither can see the deal that doesn't match any pattern yet — that's still on the rep willing to make the case.
July 25, 2026
Your Discounts Aren't a Pricing Strategy. They're a Confession the Business Case Didn't Land.
A discount request only shows up when the business case was never built. How AI turns the deal desk into a mirror instead of a haggling session.
July 18, 2026
AI Gives You Everything Walking In. It Can't Read the Room.
AI can give you everything you need walking into a room. It can't tell you who the room actually defers to. The thing great reps have always had — and always will.
July 2, 2026
You Haven't Quantified the Pain.
Most AEs identify the pain and stop. Quantified pain is the foundation of every business case that actually gets funded. Here's what changes when you put a number on it.
June 24, 2026
I Was Spending 2 Hours Building a Little League Lineup. So I Did What Any Reasonable Person Would Do.
Coaching 13 kids on a baseball field and managing a B2B sales team are the same problem. Constraints, data, methodology — and AI that clears the board so you can actually coach.
June 19, 2026
Awareness Is Not Adoption.
Mandates buy awareness. Adoption is contagious — and it starts with your top earner, not your policy. How AI actually spreads on a sales floor.
June 13, 2026
Your Weekly AE 1:1 Was Never Built for the AE.
The weekly 1:1 was built for the forecast, not the rep. How motion-specific coaching changed the cadence, frequency, and value of every deal conversation.
June 6, 2026
Personalization at Scale Used to Be a Slogan. Now It's Just How We Sell.
Discovery transcripts feed into personalized decks at every stage of the deal. How we replaced the static first-call deck with something built for the buyer in front of us.
May 27, 2026
The Ideal Sales Cycle Doesn't Live in a Folder Anymore.
Built from real win/loss transcripts, motion-specific, never finished. The Ideal Sales Cycle that actually coaches instead of collecting dust in a folder nobody opens.
May 20, 2026
Your GTM Plan Died in March. You Just Haven't Noticed.
The static annual GTM plan fails by Q2. How a live three-tab tracker changes the board update, the 1:1, and the forecast — built in an afternoon, updated in real time.