Field Notes
Sharper Stories.
Better Pipelines.
Practical writing on B2B messaging, positioning, AI search visibility, and why most homepages don't convert. Written from inside the work, not the conference circuit.
Greg Rosner
Founder of PitchKitchen · Author of StoryCraft for Disruptors
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Anchor · Magnetic Messaging Framework
How do I know if my B2B messaging is broken, not just underperforming?
Underperforming B2B messaging needs tuning. Broken B2B messaging needs rebuilding. The difference between them decides whether the next $50,000 you spend lifts pipeline or just amplifies the silence. Three tests, 30 minutes, no agency, tell you which one you're actually looking at.
9 min read
Anchor · Magnetic Messaging Framework
What changes about B2B positioning when AI is doing the buyer research?
The buyer changed and so did the first-pass evaluator. ChatGPT, Claude, Gemini, and Perplexity now summarize, rank, and filter B2B vendors before the buyer ever clicks a homepage. Three diagnostic prompts tell you in 20 minutes whether AI buyer research has already filtered you out.
10 min read
Anchor · Magnetic Messaging Framework
What does it mean when my marketing spend is going up and my pipeline is going down?
When spend climbs and pipeline falls, the problem is almost never the tactics. It's bottlenecked marketing ... stuck behind a positioning problem upstream. Five diagnostic questions you can run this week, and the four moves that fix it, in order.
10 min read
Anchor · AEO Strategy
Why doesn't AI cite my B2B company when buyers ask for recommendations?
AI engines don't cite B2B companies that sound like every other B2B company. If you're missing from ChatGPT, Claude, Gemini, and Perplexity answers, the model didn't fail to find you. It found you and decided your content didn't earn the citation slot. Five tests, the Princeton GEO numbers behind the pattern, and the order in which to fix it.
11 min read
Anchor · Sales-Marketing Alignment
Is my B2B sales cycle slow because of sales execution or because of my message?
Most B2B founders blame sales execution when cycles stretch from 80 days to 120. The cause usually sits one layer up. If your message isn't doing the work, your reps have to do it inside every call, and the deal slows under the weight of the explaining. Five tests to separate message-caused friction from execution-caused friction, plus the order to fix it in.
11 min read
All Insights
Why isn't our go-to-market working, and how do we tell which layer broke?
A go-to-market has five layers, and they fail downward. The break almost always sits above the layer you're staring at, because the layers with dashboards are the ones at the bottom. Here's the day-long diagnostic that finds the real one.
Which positioning framework should we use, and where does each one break?
Seven positioning frameworks compared by their breaking condition rather than their reputation, with the input each one quietly assumes you're bringing, and a 302-homepage finding that explains why most rollouts stall.
How we use AI before and after a sales call
A practical routine for preparing with evidence, asking better questions and catching what you missed before you follow up. From Greg Rosner’s conversation with Paul Kirch.
We finished a brand transformation sprint. Why hasn't anything actually changed?
A brand transformation sprint changes what you've decided and how clearly you say it. It doesn't change what your team does in week nine when a big wrong-fit deal shows up. Here's the honest accounting of what a strategy sprint delivers, what it leaves to you, and how to tell six months later whether it took.
Which of our products should have their own brand, and which should just be features?
Most products shouldn't have their own brand. One earns a name when it has its own buyer, its own budget line, and its own competitor. Here's the test, what a stray name costs you in sales and in AI visibility, and which architecture actually fits a $5M-$75M company.
Our champion just left. Do we work their replacement or re-open the problem?
A founder called me Tuesday about the best deal in his quarter, eighty percent in the forecast for two quarters running. Then his champion took a job two states away and the replacement went politely, permanently quiet. He didn't lose a relationship. He lost the only person who thought the problem was worth solving this year. Meet the Borrowed Deal, why chasing the successor is the one play that guarantees a slow no, and three tests to run on your forecast this afternoon.
Our buyer says they'll build it in-house. Do we fight the build or the delay?
A VP of Sales sent me the recording with a note that said "tell me where this went wrong." Thirty-eight good minutes, then the prospect's engineering lead unmuted and said "honestly, we could probably build this." The rep had a cost breakdown ready. Five months later the deal was dead and nothing had been built. Meet the Phantom Build, why arguing capability hands the room to the wrong person, and three tests to run on your pipeline this week.
What does brand strategy consulting actually deliver, and what should you refuse to pay for?
Three things are worth paying for and four common line items aren't. Here's the week-twelve test that tells them apart before you sign anything.
Which branding services do we actually need at $5M, and which can wait until $50M?
A $5M company needs a decided position written down. A $50M company needs that plus the machinery to enforce it across forty people. The branding menu looks identical at both ends, which is how founders at both ends buy the wrong row.
Our brand feels dated. Is a refresh enough, or do we need a full rebrand?
A refresh fixes expression. A rebrand reopens meaning. Both problems feel identical from the corner office, which is why most CEOs buy the cheaper one and get a nicer version of the same confusion. Meet Brand Lag, the measurable distance between the company you've become and the company your brand still describes, plus the four questions that tell you which layer actually moved.
We sell services, not software. Do we narrow the story or keep every door open?
A managing partner sent me his homepage: eleven service lines in a grid under the sentence "trusted expertise across the product lifecycle." His two toughest competitors had ten and twelve, in the same grid, under roughly the same sentence. Then he defended the list. Meet the Breadth Penalty, why an accurate description of a services firm now costs more than it earns, and three tests to run this week.
Do we need a branding agency or a marketing agency?
Both firms put messaging in the proposal and mean different artifacts by it. Here's what each one actually sells, three checks that name the gap you really have, and the four things to settle before you sign either contract.
A brand consultant owes you a decision, a marketing consultant owes you a system
The two titles overlap enough that reading profiles won't sort them. What sorts them is the accountability object, and one sentence you write before you talk to anyone.
The branding agency decision gets made before you meet a single agency
Five capable firms will hand you five different theories of who your company is, and you'll pick the one that sounded best on a Thursday. The decision that matters happens before the first pitch, and it's yours.
How can our team share AI employees without everyone building their own version?
Research. Prospecting. Proposals. Invoicing. A practical guide to sharing specialized AI employees, with human managers and clear handoffs.
We're raising prices. Do our customers re-buy or re-shop?
A CEO read me the price increase letter his lawyer had already cleared. Three paragraphs: thanks for the partnership, rising infrastructure costs, here's the new number. I asked what a customer gets for the extra nine percent and the line went quiet. Meet the Cost Confession, why the friction that used to protect a price increase is gone, and three tests to run before the letter goes out.
What actually happens in a two-week brand sprint, and what does it leave unfixed?
A two-week brand sprint is ten working days and it buys articulation: your leadership team's existing beliefs, said well. Here's the day-by-day agenda, the dependency hiding in each stage, and the four things ten days structurally can't reach.
How long does a B2B rebrand take, and what does each phase cost?
A full B2B rebrand runs four to eight months and $65,000 to $260,000 across six phases. Here's the timeline and the cost of each one, plus the phase that decides whether the other five stay on schedule.
How do we run a repositioning without breaking what's already working?
A B2B repositioning runs in six steps, and five of them are easy. Here's the sequence, the decision that sits inside each step, and the equity you protect on the way through.
We're pivoting. Do we announce the new story or grow into it?
A CEO told me his company had changed completely in eighteen months, then shared a homepage that still described the company he started. He wasn't lazy. He was waiting to feel ready. Meet the Trailing Story, and the three tests that tell you how far behind your evidence actually is.
Which sales coaching framework fits a founder-led sales team?
GROW, Sandler, MEDDIC, Challenger and Command of the Message each coach a different layer, and four of the five assume a shared story your team may not have yet. Here's the twenty-minute test that tells you which half of the problem you're in.
What actually separates the top brand messaging agencies on Clutch?
Clutch ranks brand messaging agencies on reviews, headcount, hourly rate, and project minimums. None of those predicts whether a firm will fix your positioning. Here's what the directory can't see, the four axes the good firms actually differ on, and the forty-minute pass that sorts a shortlist of three.
Do we need a fintech specialist, or will any good messaging partner do?
Most fintech shortlists get built on the filter that matters least. Category fluency buys you a week of onboarding. What actually governs a fintech engagement is whether the partner can write under legal review, hold two buyers who want opposite things, and argue against an institution your buyer already trusts. Here's the twenty-minute diagnostic to run before you talk to anyone, and the five questions that separate a firm that has done this from one that hasn't.
We're 18 months from a raise. Is our story an asset or a discount?
A founder showed me the data room he'd spent four months building, then showed me the homepage a buyer reads first. The numbers were airtight. The story took nine minutes to explain out loud. Here's the part nobody says at the kickoff: diligence teams price what they can verify fast, and everything else lands in the risk column. Meet the Clarity Discount, and the three tests that find yours while there's still time to change the answer.
We're burning runway. Do we fix the message or keep selling the one we have?
You have a countable number of months and a story you already know is mushy. The instinct is to cut the thinking and buy more doing. Run the At-Bat Count first, because it usually shows the rebuild is faster than the runway you'd spend explaining.
How do we use statistics without sounding like every competitor?
213 of 302 homepages we scored quote a hard number, and 108 of them still never say what standing still costs the buyer. Here's the difference between a statistic that sells your category and one that sells you.
How do we prove our AI is real and not just marketing?
Describing your AI better won't make a buyer believe it. Almost every B2B homepage is specific about AI now, and most are still invisible. What moves a skeptical buyer is a claim that costs something to make.
What do fintech companies with great messaging do differently?
Fintech messaging converges because category language is shared property and legal review sands off whatever's left. Here's what the companies with the clearest fintech messaging do instead, and the five checks that tell you where you stand.
Should we fire our CMO, or did we hand them a message nobody could sell?
Firing the marketing leader is the most expensive way to find out the problem was upstream of them. Before you make the call, find out whether anyone ever handed them a decided story, or just a revenue number and a brand kit.
Why do our messaging interviews give us answers we already had?
Discovery interviews hand back the answers you walked in with because the questions asked you to summarize. Truth extraction asks for episodes instead, and what comes out is the sentence you've never written down.
How do we make our messaging problem-centric without just describing pain everyone already knows?
Problem-centric messaging fails when the problem you center has no name and no price. Four tests for picking the right one, plus what our own AI-visibility tracking shows about described problems versus named ones.
How does a CRO make the case for fixing the messaging without starting a war with marketing?
The revenue leader sees it first and owns none of it. Walk in complaining about the copy and you've started a taste argument nobody can settle. Walk in with ten losses in the buyer's own words and you've handed the CEO something he can act on.
Why does our message work in person but not on our website?
Your pitch lands in the room because you're finishing it live: reading the badge, skipping what they know, picking the proof, answering the doubt before it hardens. The page has to make all four calls in advance for a stranger who never asks you anything. Across 302 scored B2B homepages, 131 companies score exactly half marks on all three signals that decide whether a message travels alone.
We need a new website. Should we rebuild on WordPress or go AI-native?
The platform argument is the third decision, not the first. The one that shapes the next three years is how fast your company can put a true answer on the internet once the new site is live. Most B2B rebuilds move the design and leave that number exactly where it was.
How do we get our value proposition past the CFO?
Finance doesn't grade your story. It ranks your request against a headcount req, a renewal, and doing nothing. Here's what your value proposition has to contain to survive that comparison, plus fresh data on the one signal 178 of 302 companies leave at zero.
How do we break into large enterprise accounts?
Large institutions buy against a funded agenda, not a capability list. Here's the narrative that gets a growth-stage company through the door, plus the three homepage signals that decide whether anyone opens it.
We just raised. Do we fix the message or spend the round on demand gen?
A funded company doesn't get a clearer message. It gets a louder one. Distribution multiplies whatever story you hand it, which means an unclear message doesn't stay a marketing problem after the wire clears. It becomes your cost structure, your board baseline, and the number you get judged against for the next six quarters.
What actually gets rewritten when we rebuild our messaging?
Three things get rewritten in almost every B2B messaging rebuild, and the product description you agonized over usually isn't one of them. Here's what changes, what survives, and the order it has to happen in.
Why should a new CRO fix the message before hiring more reps?
A new revenue leader reaches first for the levers on their own dashboard, because those are the ones they can pull without permission. Here are three tests a CRO can run in month one to find out whether the pipeline problem they were hired to fix is actually a story problem sitting upstream of it.
Which of our features actually move a buyer?
Most B2B companies describe their product clearly and still watch buyers stall. We scored 302 homepages to find out which features earn a place in the opening argument, and where the rest belong.
How do we position against a platform our buyer already owns?
The platform only has to be good enough, and it's already paid for. Here's how to win the argument you're actually in, plus what 302 scored homepages reveal about the one sentence almost nobody writes.
Why does our website undersell what we built?
Sites hedge until nothing is worth acting on. Across 302 scored healthcare software homepages, Authority and Credibility averages 0.84 out of 2 and only 7 companies reach the top band. Here's how to make claims strong enough to sell and narrow enough to defend.
7 messaging mistakes we see in every health tech pitch
Health tech pitches fail for the same seven reasons, and none of them is the product. The seven mistakes, in the order they appear in the deck, and the one gap underneath all of them.
Why does our health tech website undersell what we built?
Health tech sites hedge until nothing is worth acting on. Across 302 scored health tech homepages, Authority and Credibility averages 0.84 out of 2 and only 7 companies reach the top band. Here's how to make claims strong enough to sell and narrow enough to defend.
Why doesn't our health tech messaging move buyers?
We scored 302 health tech homepages on 19 signals. They average 1.56 out of 2 on explaining the product and 0.10 on naming what the buyer would do instead. Here's what that gap costs, and the three checks that tell you whether your page has it.
Why is marketing weak at every company in our portfolio?
When five portfolio companies in five different markets all have the same marketing problem, it stops being five problems. Here is how to tell whether you are looking at one missing asset repeating itself, and the three tests to run before you fund another agency or another marketing hire.
How does our website undersell what we built?
Here's the mechanism: every review pass sands a little specificity off every claim until nothing is worth acting on. Across 302 scored healthcare software homepages, Authority and Credibility averages 0.84 out of 2 and only 7 companies reach the top band. Here's how to make claims strong enough to sell and narrow enough to defend.
7 messaging mistakes we see in every sales pitch
Pitches fail for the same seven reasons, and none of them is the product. The seven mistakes, in the order they appear in the deck, and the one gap underneath all of them.
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