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Most early stage SaaS pipelines are full of interested people
Most early stage SaaS pipelines are full of interested people, not buyers. That is why the forecast looks healthy right before it collapses. A founder told...
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Hugh Jackman froze on a rock face as a kid
Hugh Jackman froze on a rock face as a kid. His friends laughed. That moment explains something every leader, founder, and operator faces at work. Fear show...
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Your best sales calls can become posts your buyers use
Your best sales calls can become posts your buyers use to build internal support. The language is already there. Budget concerns, closed-lost reasons, rollo...
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Your office calendar is not proof of progress
Your office calendar is not proof of progress. It might be proof you have stopped learning. Simon Sinek tells the story of two lumberjacks. Same hours....
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The things you keep avoiding in business are getting more
The things you keep avoiding in business are getting more expensive. The message you keep drafting but never send. The decision you keep circling. The mist...
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The best sales teams read the fear behind the signal
The best sales teams read the fear behind the signal. Cognitive bias shows when a proof request is really a risk request. When a next step is only politenes...
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Tom Cruise lead-role movies have grossed $12.7B
Tom Cruise lead-role movies have grossed $12.7B. But he did not learn movies by staying in the actor box. No film school. No acting class. No formal path....
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I had a dream since I was 12 - to
I had a dream since I was 12 - to be a published author. Today- that dream came true. For the first time in my life, I can say I’m an author! Update: its a Be...
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Your champion is not taking your pitch into the next
Your champion is not taking your pitch into the next meeting. They are taking one sentence. And that sentence decides whether the deal moves or dies. Ear...
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The quickest way to lose a business deal is to
The quickest way to lose a business deal is to make someone feel small. A buyer challenges your price. A partner pushes back on your plan. An investor ques...
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A rep I know sells IT infrastructure software to six
A rep I know sells IT infrastructure software to six industries. Last month, he had two sales calls with regional bank CIOs. He could not name the bank’s prim...
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Tversky & Kahneman did a study that proved the wrong
Tversky & Kahneman did a study that proved the wrong frame can kill the right idea. Your buyer is not only judging the facts. They are judging whether those f...
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A leadership team can train a company to see danger
A leadership team can train a company to see danger in every slow month. Every hard customer. Every missed target. Tony Robbins proves it with two colors....
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Your B2B deal can pass MEDDPICC inspection and still be
Your B2B deal can pass MEDDPICC inspection and still be wrong. That is the problem in Issue 12 of The Closer & The Architect. The deal had every box checked...
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Business conversations rarely get stuck because people disagree
Business conversations rarely get stuck because people disagree. They get stuck because people agree too quickly. Chris Voss spent years negotiating with pe...
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A LinkedIn filter is not an ICP
A LinkedIn filter is not an ICP. It just looks like one. That is the sales trap. A B2B SaaS founder builds a list of IT leaders at US regional banks using...
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Your body hears the way you speak to yourself
Your body hears the way you speak to yourself. So does the way you work. One apple. Five sentences. “I’m not good enough.” “Why am I like this?” “I ru...
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Your MEDDPICC data is lying to you
Your MEDDPICC data is lying to you. The issue is not the framework. The issue is what you use it for. I wrote about Munger & the Inversion Technique a co...
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When a business person stops pushing, it is not always
When a business person stops pushing, it is not always burnout. Sometimes they have stopped seeing effort change outcomes. The sales lead stops following up...
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Your mindset probably does not sound like fear
Your mindset probably does not sound like fear. In B2B, it often sounds like certainty. “I know this market.” “Our buyers do not respond to that.” “That c...
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You are running your quota race with ankle weights on
You are running your quota race with ankle weights on, and calling it hard work. You did not miss quota because you stopped working. You missed because the...
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Your business standards are not fully yours
Your business standards are not fully yours. They are borrowed from the founders, leaders, and teams you work with daily. Rosenthal proved this at Spruce El...
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Your top rep closed four deals last quarter
Your top rep closed four deals last quarter. Your next three reps combined closed two. Same product. Same market. Same comp plan. In the CRM, that gap...
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Bad quarters make B2B leaders overcorrect
Bad quarters make B2B leaders overcorrect. Good quarters make them believe the model is better than it is. Both are dangerous. Because the real risk in B...
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The B2B SaaS industry sold you a research tool and
The B2B SaaS industry sold you a research tool and called it buyer intelligence. That is the lie nobody wants to say out loud. LinkedIn Sales Navigator give...
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Reps do not lose Enterprise because Professional is cheaper
Reps do not lose Enterprise because Professional is cheaper. They lose Enterprise because Professional looks sensible. That is where deal size disappears....
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Ghosting does not kill most deals
Ghosting does not kill most deals. Anxious follow-up does. Chris Voss, former FBI negotiator, uses a clean sales line when a buyer goes quiet: “Have you g...
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Most B2B conversations get harder when you walk in holding
Most B2B conversations get harder when you walk in holding a hammer. Everything starts to look like something you need to break through. You stop listening....
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Your ICP is not your buyer
Your ICP is not your buyer. “CMO in a Series B SaaS Company” is not an ICP. It is a LinkedIn filter. A filter tells you who might answer. It does not...
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Your buyer did not choose the incumbent because your ROI
Your buyer did not choose the incumbent because your ROI was weak. Cialdini called it authority bias. Your buyer called it the safer bet. They chose the shado...
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Your recurring business problem may be protecting an old assumption
Your recurring business problem may be protecting an old assumption. There is a line often linked to Einstein: “The significant problems we have cannot be s...
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Some days grind you down so badly you forget you
Some days grind you down so badly you forget you are being shaped, not ruined. A pencil becomes useful because it can survive being sharpened. Careers work...
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Fear rarely looks like fear in a sales team
Fear rarely looks like fear in a sales team. It looks like urgency. Pressure. Risk management. Being realistic. The deal goes quiet, so you over-explai...
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Your champion is carrying a receipt, not a scorecard
Your champion is carrying a receipt, not a scorecard. They are not defending the better vendor. They are defending the decision they already had to justify....
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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...
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For B2B professionals, shortcuts create careers that
For B2B professionals, shortcuts create careers that eventually collapse under their own weight. Kobe Bryant played an entire summer without scoring one poin...
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B2B careers are not only shaped in meetings
B2B careers are not only shaped in meetings. They are shaped by the private rooms you keep walking into. Michael Jordan’s first NBA test was not on a court....
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Your buyer just asked the question most sellers try to
Your buyer just asked the question most sellers try to survive. “What can’t your product do?” The answer matters less than what you do next. Weak sellers...
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In B2B sales, winning is not about how hard you
In B2B sales, winning is not about how hard you hit. It is about how hard you can get hit and keep moving forward. And sales will punch you in the guts....
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People can feel the moment you stop listening
People can feel the moment you stop listening. It usually happens quietly. On a sales call, you hear a job title and decide how much power they have. You h...
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Sales teams lose deals because they trust old pain more
Sales teams lose deals because they trust old pain more than current facts. The account is not dead. Your CRM memory is stale. There’s a moment in that tan...
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B2B sales reps will spend $2,000 on golf this year
B2B sales reps will spend $2,000 on golf this year, but won’t spend $300 to get better at selling. That gap shows up in quota outcomes. Average quota atta...
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In B2B, work starts to wilt when the person presenting
In B2B, work starts to wilt when the person presenting it needs approval to stand tall. You see it the moment the room pushes back. A senior leader asks a h...
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Your ICP is often wrong for one simple reason
Your ICP is often wrong for one simple reason. It is built from anecdotes, not real buyer data. That is like judging a full image from a few pixels in the c...
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Your B2B deal is stuck because your champion is pointing
Your B2B deal is stuck because your champion is pointing at smoke. The fire is somewhere else. I learned that from my retired neighbor. He had never sold...
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Your B2B career can look stronger while you feel weaker
Your B2B career can look stronger while you feel weaker. Your title improves. Your pay improves. Your room gets bigger. People start taking you seriousl...
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Your B2B deal did not lose to the competitor
Your B2B deal did not lose to the competitor. It lost in the buying process you did not control. Week eleven. The POC was clean. Your champion was in....
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B2B sales is not a microwave meal
B2B sales is not a microwave meal. It is a recipe. And most people ruin it by trying to rush it. A deal goes quiet. A buyer stops replying. A proposal...
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Your sales pitch is setting off the fire alarm
Your sales pitch is setting off the fire alarm. The buyer is not looking for fire. They are looking for the exit. That is what happens when a B2B prospect...
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Your B2B career rarely stalls because you made one bad
Your B2B career rarely stalls because you made one bad move. It stalls when the water around you stops moving your thinking. The conversations in your tea...
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Your B2B deal is not stuck
Your B2B deal is not stuck. You handed the helm to the buyer. Enterprise deals break when the weather changes. A new stakeholder steps on board. Budget...
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Your work is like air in a room
Your work is like air in a room. If no one values what you bring to the room, you are in the wrong room. In the wrong place, people just breathe it in and m...
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Your prospect should not feel like they are being sold
Your prospect should not feel like they are being sold to in complex B2B deals. They should feel like they are helping shape the solution. That is what make...
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The deal does not die when The Skeptic says no
The deal does not die when The Skeptic says no. It dies when The Skeptic turns certainty into doubt. 47 technical questions land at once. Security. Inte...
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Office politics do not break a company all at once
Office politics do not break a company all at once. They start as a hairline crack in the foundation, easy to ignore until the building no longer feels safe....
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Your price rarely gets killed in the proposal
Your price rarely gets killed in the proposal. It gets killed by the first number you say out loud. Anchoring bias helps explain why. That first number b...
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When the pressure goes up, most people get faster
When the pressure goes up, most people get faster. That’s also when they become harder to work with. Your calendar gets full. Your inbox gets louder. Th...
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Objections are usually handled like flooring the gas when the
Objections are usually handled like flooring the gas when the car is already sliding on ice. The sales rep feels the call slipping, so they add more force....
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Rust Cohle from 𝘛𝘳𝘶𝘦 𝘋𝘦𝘵𝘦𝘤𝘵𝘪𝘷𝘦 said it better than most
Rust Cohle from 𝘛𝘳𝘶𝘦 𝘋𝘦𝘵𝘦𝘤𝘵𝘪𝘷𝘦 said it better than most people ever will. Say what you can do. Then do it. That sounds simple until you watc...
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Your deal can smell fear before it sees price
Your deal can smell fear before it sees price. “Can’t” is the worst word that’s written or spoken. Not because the buyer hears it. Because the buyer hears...
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Your deal can look done 14 days before signature
Your deal can look done 14 days before signature. Then your Champion becomes a Ghost. The quarter dies. A new stakeholder walks in cold, with a competito...
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Freedman & Fraser studied what small commitments do to later
Freedman & Fraser studied what small commitments do to later decisions. Cialdini later made commitment & consistency familiar. Most B2B sales training lives...
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Your deal is not stuck on price
Your deal is not stuck on price. It is stuck on the moment the buyer imagines having to explain a bad decision. In B2B tech sales, skepticism gets treated...
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In sales, you are going to get hit
In sales, you are going to get hit. It’s gonna to hurt- and leave a mark. 4 or 5 deals a quarter will fall apart. A deal you were counting on goes quiet....
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Your prospect reads your AI message the same way
Your prospect reads your AI message the same way you read a menu full of stock photos. Everything looks fine. Nothing looks real. “Just checking in.”...
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Schwartz studied why more choice reduces satisfaction
Schwartz studied why more choice reduces satisfaction. Iyengar showed it reduces decisions. In one study, only 3% bought when shoppers saw 24 jam options....
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Your pipeline goes quiet & the hunt starts to feel
Your pipeline goes quiet & the hunt starts to feel like work. That is usually where the difference shows up. Not in the win. In how people show up when not...
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You are losing deals to The Doubt in your pipeline
You are losing deals to The Doubt in your pipeline. Not when the buyer says no. Much earlier. Usually after 2 or 3 deals slip, a prospect ghosts, and a 9...
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Your team does not believe what you say. Talk's Cheap
Your team does not believe what you say. Talk's Cheap. They believe what you let slide in meetings, delivery, & client work. Rock's loud. In B2B, trust is...
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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....