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Your buyer is not stuck
Your buyer is not stuck. They are paralyzed by inertia. And most sellers reinforce it. That is why 40-60% of deals end in no decision.. The issue is exp...
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I have never been more afraid in my entire life
I have never been more afraid in my entire life. My heart pounded in my chest as sweat poured down my face. My entire body shook. I stood behind a podi...
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Your biggest deals are not won where
Your biggest deals are not won where most people think they are. In sales, 72 percent of your time is spent on work that does not close deals, yet most...
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You think your buyers
You think your buyers make decisions independently. They do not. 75% of people gave an answer they knew was wrong just to avoid standing alone. Your...
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You do not lose career momentum in
You do not lose career momentum in one bad quarter or a lost deal at work. You lose it in patterns you keep excusing. Fear slows action. Doubt clouds jud...
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You are still researching accounts manually, & it is costing
You are still researching accounts manually, & it is costing you deals. I gave Claude one instruction at 8am. By 8:15, a full prospect brief was done. No...
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Your $750k deal did not stall because your champion went
Your $750k deal did not stall because your champion went quiet. It stalled because the gatekeeper kept you below the person who could approve it. In enter...
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Your prospect decides in the first few seconds
Your prospect decides in the first few seconds whether you sound real or robotic. That decision can kill the call before it starts. They do not care that...
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Your deal is not stuck because the buyer needs more
Your deal is not stuck because the buyer needs more proof. It is stuck because no decision feels safer than change. That is where a lot of B2B tech deals st...
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Your deal is not stalling on price
Your deal is not stalling on price. A lot of them die when the buyer feels pushed. 40 to 60 percent of B2B deals end in no decision. This is how sales team...
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Your deal did not slip at the end
Your deal did not slip at the end. You picked up a prize you were never going to keep. Demo done. Champion sold. POC passed. Then the claw opens. Th...
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Your deal did not stall because your champion went quiet
Your deal did not stall because your champion went quiet. The Blocker got there first. 9 months. 15 stakeholders. $500k in pipeline. And you built the whol...
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Your deal looked real
Your deal looked real. The buyer said it was urgent. You rushed the demo. Then nothing happened. No decision. No next step. No reply. You lost the...
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Your mid-market pipeline will break if leadership
Your mid-market pipeline will break if leadership pushes into enterprise before the business is ready. A 90 day deal turns into 12 months, then dies in sec...
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Your friends think B2B sales is first class flights
Your friends think B2B sales is first class flights. And a huge expense account. Last quarter you missed quota by 15 percent. You spent the weekend wonderi...
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Your team rehearses on live pipeline
Your team rehearses on live pipeline. An athlete who did that would be cut by Tuesday. A quarterback does not figure it out mid-play. A surgeon does not impro...
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Most pipelines are full of zombie deals
Most pipelines are full of zombie deals. They should be dead, but you keep bringing them back. You open your pipeline. You already know what you are going to s...
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War outside. Rain on the tent
War outside. Rain on the tent. A sales deal goes quiet. Calm inside is the job. That is what I take from this Marcus Aurelius quote. Not as a way to care les...
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Your deal didn’t slip
Your deal didn’t slip. You never had the route to yes. Feb 28. Recalculating. March 15. Recalculating. End of Q1. Recalculating. TBD. Nothing changed. You...
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You lost a deal this quarter you should have won
You lost a deal this quarter you should have won. The product was good enough. The way you framed it wasn’t. Most sellers open with upside. “Save time.” “Impr...
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Your Q1 forecast is due
Your Q1 forecast is due. The dominoes already started falling. You just haven’t said it out loud yet. Your pipeline says one thing. Your gut says another. Ev...
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The “closer” is the weakest performer on your team
The “closer” is the weakest performer on your team. Not occasionally. Systematically. Around 70% of reps missed quota last year. Win rates sit around 20%. Av...
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Most deals do not die for the reasons you think
Most deals do not die for the reasons you think. They die because the seller misreads the pushback. The buyer says: “Send something over.” “We’re fine for now...
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AI is not replacing sales reps
AI is not replacing sales reps. It is exposing which ones were never selling. For years, a large part of the sales job has been information work. Researching...
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Anger in a meeting spreads the way acid spreads through
Anger in a meeting spreads the way acid spreads through glass. At first, it is almost invisible. A sharper tone. A dismissive comment. A look that makes the di...
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Your buyer already has a strong opinion about your company
Your buyer already has a strong opinion about your company. It was not formed on your website. It did not come from Google. Or a review site. They asked AI....
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Deals rarely stall because the buyer isn’t convinced
Deals rarely stall because the buyer isn’t convinced. They stall because the buyer is anxious. Robert Cialdini studied why people say yes. Eric Knowles studied...
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A seller showed me his AI follow up
A seller showed me his AI follow up. Nine emails in my inbox used the same line. Same opening. Same structure. Same careful corporate tone. He had spent twent...
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Deals sometimes move after weeks of silence
Deals sometimes move after weeks of silence. No new pitch. No new deck. No new discount. Yet the decision suddenly moves. What changed? Usually not the offer...
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Your first sales call of the day should never be
Your first sales call of the day should never be practice. Yet in many sales teams, it is. A qualified buyer answers the phone and becomes the rep’s warm up....
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A lot of B2B pipelines look healthy
A lot of B2B pipelines look healthy. They aren't. They are just full of the wrong buyers. And most teams only realize it months later, when “strong pipeline”...
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Hannibal didn’t give up crossing the Alps
Hannibal didn’t give up crossing the Alps. He decided to find a way... or make one. Some B2B deals feel like that. A champion leaves. Procurement joins late....
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2026 might be the year your product gets cut
2026 might be the year your product gets cut. Even if it works. Not because budgets are shrinking. Because AI budgets are growing. Many companies are funding...
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One question quietly decides many Commercial AE interviews
One question quietly decides many Commercial AE interviews. Most candidates struggle with it. Not because they lack experience. Because they cannot explain the...
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Your champion is learning AI
Your champion is learning AI. And quietly preparing to leave. That is enterprise selling in 2026. Boards are cutting headcount to fund AI. CFOs are freezing s...
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That 247 word cold email isn’t bad
That 247 word cold email isn’t bad. It’s lazy thinking dressed up as effort. AI made it easier to produce words. It did not make you sharper. And your buyer c...
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Your deal didn’t die at pricing
Your deal didn’t die at pricing. It crashed into the rocks halfway through the demo. Most technical demos are harbor tours (h/t to Peter Cohan). Safe. Polishe...
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Your six figure deal is one resignation away from dying
Your six figure deal is one resignation away from dying. If your deal has one contact, it’s fragile. Not because they aren’t strong. Because they’re alone....
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AI isn’t your sales team’s magic wand
AI isn’t your sales team’s magic wand. It’s a tool. And most teams are using it wrong. They assume better prompts will rescue weak deals. So they throw AI a...
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Opening with ROI on a first call is not confidence
Opening with ROI on a first call is not confidence. It is a tell. It tells the buyer you have not found the real cost yet. Seventy percent of reps missed quo...
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If you missed quota last quarter, this could be why
If you missed quota last quarter, this could be why. Someone on your team stopped typing. You did not. The busiest rep still drafts from scratch. The top rep...
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You are running POCs that are designed to lose
You are running POCs that are designed to lose. You are really selling to finance & running the proof for IT. The software works. Security signs off. The inte...
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Your deal did not stall
Your deal did not stall. You made it easy for the buyer to ignore. They said it was urgent. You believed them. You presented. Nothing moved. Here is why. Y...
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Your prospect knows you used AI
Your prospect knows you used AI. They can tell in seconds whether you understand their issues. That’s the new bar. Anyone can generate a polished message in 1...
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"I'm not interested."
"I'm not interested." That sentence kills more calls than bad targeting. Every rep has heard it. And most are trained to fight it. Explain more, pitch harder,...
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AI didn’t make bad sellers better
AI didn’t make bad sellers better. It exposed them. I see reps send 200 “personalized” messages without doing even basic persona research. No segment defined...
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Your prospects are not ghosting you. Are they mirroring you
Your prospects are not ghosting you. Are they mirroring you? A helicopter circles the Las Vegas Sphere. The screen reads: "YOU GAVE AI ZERO CONTEXT. IT GA...
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Buyers do not kill deals
Buyers do not kill deals. They let them drown. The demo lands. Stakeholders nod. The use case makes sense. Then replies slow down. Details thin out. “Circling...
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Most cold calls fail in the first 7 seconds
Most cold calls fail in the first 7 seconds. Not because reps lack confidence. Because the opening line gives the buyer no reason to care. “Is now a good time...
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Nine ways to blow an enterprise AE interview
Nine ways to blow an enterprise AE interview. All of them sound like good answers. Last week I posted about how enterprise interviews are audits, not conversa...
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After the final POC, optimism spikes
After the final POC, optimism spikes. That is when many deals die. The AE feels confident. The SE feels validated. The champion says, “This is exactly what we...
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In 2026, the gap between good reps and top reps
In 2026, the gap between good reps and top reps will not be effort. It will be how they use AI across the entire deal cycle. Right now, 72% of a salesperson’s...
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If your pipeline meetings feel like a wrestling match
If your pipeline meetings feel like a wrestling match, you don’t have a performance problem. You have a visibility problem. “Where’s the proposal?” “How did w...
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Elite athletes don’t trust how the game felt
Elite athletes don’t trust how the game felt. They watch the film. In this video, Bob thinks he crushed his sales call. Confident. Relaxed. Already spending...
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Enterprise interviews are not conversations
Enterprise interviews are not conversations. They are audits. You are not being judged on how well you come across. You are being judged on whether you can ru...
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Most AI output fails for the same reason most sales
Most AI output fails for the same reason most sales messages fail. The thinking never happened first. Sellers say AI is inconsistent. What they mean is: “I di...
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The best deals you’ve ever seen were already won underwater
The best deals you’ve ever seen were already won underwater. What you’re looking at is just the tip of the iceberg. Quota smashed. Big logos closed. Inbound le...
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AI isn’t giving you bad output
AI isn’t giving you bad output. You’re giving it unstructured input. You’re not bad at prompting. You’re missing a system. If you work in B2B tech sales, you...
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Your CRM isn’t a graveyard
Your CRM isn’t a graveyard. It’s full of zombie deals waiting on timing. Many reps treat their Closed-Lost column like a cemetery. Once a deal dies, it stays b...
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If your AI writes emails like these puppets, the problem
If your AI writes emails like these puppets, the problem started before the prompt. Most bad cold emails aren’t bad because of wording. They’re bad because n...
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You play the game perfectly
You play the game perfectly. Nail the demo. Get the champion. Win the technical POC. The claw grabs the deal. Then it slips. No economic buyer. No signature a...
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Top performers don’t practice on prospects
Top performers don’t practice on prospects. They practice on AI. Many reps do it. Some use the first few calls of the day to “warm up.” Then burn qualified le...
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"AI doesn't sound like me."
"AI doesn't sound like me." That's not a model problem. That's a you haven't taught it anything problem. You gave it three prompts, got generic output, and d...
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AI already introduced you to your buyer. You weren't in
AI already introduced you to your buyer. You weren't in the room. Your buyer's first impression of you was written by an algorithm. Before the call. Before the...
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Discovery isn’t broken. B2B sellers are showing up unprepared
Discovery isn’t broken. B2B sellers are showing up unprepared. “So tell me about your business.” “What keeps you up at night?” “Who else needs to sign off?” O...
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Stop trying to be just a “relationship seller.”
Stop trying to be just a “relationship seller.” Start thinking more like a GTM engineer. B2B Tech Sales is stuck in a false binary: human seller vs AI seller....
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How often do you feel less like a B2B sales
How often do you feel less like a B2B sales rep… and more like a data entry clerk? Be honest. Look at your calendar from last week. How much time was spent ac...
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When you sense a deal slipping, do you start talking
When you sense a deal slipping, do you start talking? The tough question lands. Or worse — silence. Your brain panics: Fix it. Say something smart. Explain th...
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If you’re forecasting single-threaded deals, you’re lying to yourself
If you’re forecasting single-threaded deals, you’re lying to yourself. If you only have one contact in a deal, you don’t have a deal. You have a single point...
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AI is helping some sellers generate 77% more revenue
AI is helping some sellers generate 77% more revenue. The gap isn’t access. It’s consistent use. That stat comes from Gong Labs, which analyzed 7.1 million opp...
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Half of B2B sellers are using AI today
Half of B2B sellers are using AI today. Most are falling behind anyway. The single-model seller is getting crushed. You know the type. One AI for everything....