Everyone can feel the moment a sales call goes off the rails.

The enterprise Account Executive finally gets a highly-qualified prospect on Zoom. The discovery goes well. The AE shifts into the pitch. Two minutes in, the prospect interrupts.

“Oh, I get it. So you guys are basically like [Commodity Competitor X] for [Vertical Y]?”

The air escapes the room.

Now, the AE has to spend the next 5 minutes backpedaling. Playing defense. Explaining what the product isn’t. By the time they actually get back to pitching what the solution is, the prospect has tuned out. Scratched your name off the shortlist.

Because they already bought something just like this, or at least, something “good enough.”

B2B tech companies today aren’t just losing deals to their direct competitors. They’re losing them to the wrong mental bucket. And if enterprise buyers don’t understand where you fit within their larger tech stack, they will default to the most familiar (and cheapest) tool they know.

Last year I worked with a client in the EdTech space who built something genuinely new: unified payments and accounting for extracurricular activities like prom photos, pizza lunches, and soccer uniforms. Because they were carving out a space no one else occupied, every sales conversation turned into a defensive maneuver.

Prospects couldn’t figure out what category to put them in, so they compared them to the solutions my client looked most like — bookkeeping software, payment portals, student information systems. The reps were spending a quarter of their calls fighting their way out of those boxes.

When buyers put you in the wrong bucket, they assume they already have the tools they need to solve the problem your platform solves. That assumption doesn’t just put the deal in danger; it can be dangerous for the buyer.

The million-dollar blindspot

For this EdTech client, the wrong bucket was the school district’s massive ERP system. District CFOs assumed their existing financial software was already doing the job.

It wasn’t.

While the legacy ERP managed 95% of the district’s budget —payroll, facilities, buses— it completely ignored the remaining 5%. That 5% was literal cash sitting in teachers’ desk drawers. It was field trip money tracked in spiral notebooks and hot lunch funds managed on fragmented Excel spreadsheets.

To an enterprise buyer, 5% looks like small potatoes. But that unmanaged cash is where the lion’s share of school fraud, failed audits, and career-ending local headlines happen. And in large public school districts, that 5% can amount to millions of dollars every year.

As long as buyers viewed my client as just another payment portal or a redundant ERP feature, the deals stalled. We had to shift the context. The story couldn’t just be about digitizing student payments or delivering better parent experiences (that was all secondary messaging). The storyline had to be about exposing a glaring, dangerous vulnerability in the CFO’s own office — and providing the only purpose-built platform to lock it down.

The marketing toll

The “confused-for” problem begins on the marketing side of the revenue house.

When a company lacks an overarching storyline, the natural instinct is to compensate by turning up the volume. Buying more keywords. Hiring a PR firm to secure some high-profile placements. Pushing out SEO content to drive inbound traffic. But because your messaging sounds just like every other vendor in your broader space, you end up spending a ton of money and generating the wrong leads.

I heard this play out with a scaling HR tech company recently. They were in an incredibly crowded space, fighting against massive incumbents. They were spending $10k a month on an SEO agency that was producing content that ranked beautifully, but had absolutely zero connection to what their software actually did.

They were paying another massive retainer to a PR firm that was pitching a completely different narrative to the media. The internal team was left trying to hold it all together by feeding brand guidelines into ChatGPT.

There was zero connective tissue.

The VP of Marketing laid it out perfectly. She knew she could mitigate the pain temporarily by throwing even more budget into paid channels, but that would just amount to optimizing and scaling bad messaging.

When you fragment your go-to-market across isolated agencies without a singular, strategic story holding it all together, you are paying a premium to confuse your own buyers. Your CAC skyrockets because you’re paying to acquire people who are looking for the thing you just spent 20 minutes on a Zoom call proving you’re not.

An alternative take on the “alternatives” slide

Enterprise buyers are inherently skeptical. If you don’t proactively address the other tools in their tech stack — including the ones you don’t actively compete with — they will spend your entire pitch trying to categorize you in their head.

You have to address the alternatives early.

Credit to April Dunford and her influential book, Sales Pitch. She advocates for laying out the competitive alternatives in the first 10 minutes of a discovery conversation. But in her framework, the “alternatives” slide is distinct from the “insight” slide.

In the Storyline method, those two things are intimately connected. Your point of view on the market and competitive landscape is the insight. Both are fundamental building blocks of the storyline.

I recently worked with a Series C company whose platform powers connected fleets of commercial and industrial robots. The problem was that buyers were constantly confusing them with closed-system hardware manufacturers, or assuming they needed to hire an expensive systems integrator to build a bespoke solution that worked for their business and customers.

We built a sales deck that framed the market landscape right on slide two. But we didn’t just list competitors or “alternative approaches.” We used the landscape to add weight to their core storyline.

The slide laid out the two dominant (and flawed) approaches in their market. On one side, vendors selling “physical AI” — humanoid robots that look amazing in a lab demo but become a massive liability on an active factory floor. On the other side, vertical hardware vendors operating within closed ecosystems that don’t allow businesses to integrate or scale.

By anchoring their storyline on real-world AI my client attached themselves to the well-funded “physical AI” category while emphasizing that their platform is actually built for high-stakes retail and industrial use cases. AI built to solve real business problems, in dynamic physical spaces, today. What could have felt like generic brand positioning became a credible commercial story.

The alternatives slide isn’t just a way to explain what you do and how it’s different. It’s a way to show that you’re solving a completely different problem – one the buyer might not have even realized they had. Not just what and how but why and why now. It’s market education and competitive differentiation in one fell swoop.

You need to solve the confused-for problem before you solve the positioning problem. What you do is only relevant if the customer understands the context you both operate in.

The power of proactive framing

Positioning tells the market what you do. The storyline frames how they should think about it. You need to elevate the narrative above the feature level so you aren’t just fighting a war of technical attrition.

Take a client I’m working with that sells a powerful platform for building and deploying AI agents for customer support. If they walk into a room and just pitch what they do, the immediate instinct of an enterprise buyer is to lump them into the generic “chatbot” category, or assume they’re just another AI bolt-on to an all-in-one CX suite like Zendesk or Genesys.

We’re building a storyline to prevent those assumptions from taking hold. One that’s anchored in their actual differentiation. Not just their product but their pricing strategy, their ICP, and their opinionated executive POV.

We can’t just lead with AI specs or deflection metrics. If buyers put them in the generic “AI customer experience” bucket, my client is suddenly fighting against much better-known and better-funded companies.

Everyone in this category — like most crowded categories — is selling the same outcomes, and saying the same thing. That includes AI-native vendors my client competes with and legacy incumbents they actually integrate with, but are getting confused for nonetheless.

Their storyline is currently under construction. Watch this space.

The story moat

If your sales team spends more time explaining what you’re not than what you are, you don’t have a positioning problem. You have a different kind of problem:

A confused-for problem. A storyline problem.

And in a world of feature parity and AI slop, story is the only moat left.

You’ve flown to Korea for a dinner with the VP of Innovation at a $12B global manufacturing conglomerate. The steaks arrive, the small talk about kids and travel winds down, and you can feel the lull coming. It’s the same lull I’ve left you in before, where the product feels like a demo, the questions feel like a discovery call, and you end up talking about the weather.

This time is different.

The VP is cutting into his steak. Instead of interrogating him about his pain points you lean in and share an observation. “Everyone is pouring capital into general-purpose humanoid robots. But from what we’ve seen, the technology that goes viral in a lab demo becomes a massive liability on an active factory floor. How is your team navigating all the physical AI hype?”

The dynamic instantly flips. You’re an industry peer discussing a shared reality. The pitch hasn’t even entered the room.

That scene is drawn from a sales conversation I watched a robotics client of mine run. Some context, because the context is the whole point. The vendors taking up oxygen in their space are selling the dream of general-purpose humanoid robots that can do anything, but that dream is largely vaporware.

My client built an autonomy software platform that can power any purpose-built robot, which means they turn their partners’ visions into something that ships. Their storyline pits “physical AI” – the VC flavor of the month – with real-world AI: Deploying AI-powered robots to solve real customer problems in real commercial and industrial spaces, today.

In a sales conversation, the first job is to establish the context of the market. The need for enterprise robotics is real, the AI mandate is here, and the market keeps answering with cool demos and closed ecosystems. They call that disconnect the autonomy gap, the space between hype and reality, between cool robots and sellable robotics solutions.

Framing the conversation that way pulls a customer in before anyone has said a word about the product.

Who leads the conversation

The steak dinner is the most visceral version of a question that runs through the entire sales process: who leads the conversation.

Without a storyline, the seller is reactive. The standard rapport-then-discovery sequence puts the buyer in the driver’s seat, and in complex enterprise sales, where the buyer often can’t articulate the underlying problem yet, that’s where deals go quiet. The buyer describes symptoms, the seller nods along, and a few weeks later, somebody decides to push this to next quarter.

I have another client that used to run their discovery calls without bothering to pitch at all. I’m not saying you need slideware, but they were letting the prospect lead the conversation entirely. The prospect would lay out their pain points and needs, and the team would validate them with something like, “Yeah, we do that,” or “That’s not very surprising, all the businesses we work with are experiencing this.” That may seem validating, but it’s not even a little bit reassuring.

Now they open the call themselves: “Before we hear more about your business and what our solution does, let me tell you a little bit about what we’re seeing across the highly-regulated enterprises we work with.” They talk about the urgent AI mandate and how hard it is to deploy AI swiftly and safely without a layer of assurance. They cover the other solutions to this problem and where each falls short. And then they ask the prospect to validate: “Does this resonate with you?”

By framing the context and the problem, they demonstrate empathy and credibility rather than sounding like just another salesperson insisting they understand their problem better than anyone else, and have just the key to solving it.

The discovery call

Same principle, different room. Discovery still matters, but it should sound like a genuine back-and-forth between peers rather than a fishing expedition. Shop talk, not sales speak. And the storyline is what gives you something to talk about.

Context before problem, problem before solution. The context earns the problem. When you lead with context, discovery stops feeling like an interrogation and becomes a mutual validation of worldview.

On the discovery call with that same manufacturer, instead of grilling the prospect about warehouse square footage, the rep used the storyline to test alignment. They framed the market:

“We believe that safely managing a fleet of boring, purpose-built robots at scale is infinitely more valuable to a supply chain than waiting a decade for the perfect humanoid.”

The prospect immediately agreed, then started venting about how their current closed-ecosystem robots were failing to communicate with each other.

In other words, the buyer ended up doing discovery on themselves, because the seller gave the conversation the right container.

The room the AE is never in

In an enterprise deal, your champion has to sell your solution internally. To a CFO who wasn’t on the demo or an IT procurement committee evaluating half a dozen vendors on a spreadsheet. Resonance is what survives the internal game of telephone, and the storyline is how you pass the champion test.

The VP of Innovation who took that call now has to sell the platform to the head of their logistics division. If the rep had pitched features, the champion would walk into that internal meeting and say, “This vendor sells autonomy software for commercial robots.” Procurement would kill the deal on the spot, because they already buy robots that come with their own software.

But the rep armed them with a storyline. So the champion can walk into that board room or another dinner (maybe a fancy lunch this time) and say, “We’re currently buying closed-loop hardware that creates operational silos. This vendor provides the core autonomy platform that turns our entire facility into a single, orchestrated system.”

The first version describes a product for which the company already has a line item. The second describes a problem the company didn’t yet have a name for. Which narrative do you think survives the buying committee?

Story as scaffolding

Today’s issue is all about the sales conversation, but the storyline belongs to everyone, not just the AE.

The SDR should hint at it in outbound. The solutions engineer should refer back to it throughout the demo. The forward-deployed engineer should build their onboarding and deployment methodology on it. It should be enshrined in the customer success maturity model and in the product itself. And, of course, on the homepage and in the PR boilerplate.

The storyline articulates how the company sees the world and how it drives outcomes for the customer. It gives your team something to say when the pitch is over. At dinner, on the discovery call, and in the rooms you’ll never be in, where a champion is retelling your story to people you’ll never meet.

Your sales team can’t be in every room. Your storyline must be.

“I get why we need an overarching story,” the CRO told me in our kick-off call, “but I just don’t see how you’re going to skin this very hairy cat.”

He was managing two businesses under one roof. A legacy e-commerce solution serving founders running Shopify stores, and a newer enterprise solution serving product and engineering leaders at companies like Qatar Airways and BMW, protecting the GitHub repositories, Jira projects, and Confluence documentation their entire teams depended on.

Two buyer segments with almost nothing in common: different sales cycles, different stakeholders, different everything.

Before I arrived, the company had built multiple separate go-to-market motions, each organized around the specific platforms they backed up. Shopify. Jira. Monday.com.

For the marketing and sales team, the work had compounded over time. More integrations meant more dedicated messaging, more demand gen campaigns, more product-specific proof points. But in building all of that out, something had gotten lost. They were marketing the integrations, not the product.

The story that connected everything eventually boiled down to a single word: shipping.

When a Shopify store’s catalog disappears, the business can’t ship orders. When an engineering team loses access to a GitHub repository, they can’t ship code. The real problem in both cases isn’t data loss in isolation. It’s that the business stops moving.

And for large, technology-dependent enterprises (that is all enterprises these days), “shipping” means something concrete and visceral, whether you’re talking about a warehouse fulfilling physical orders or a software team pushing product to production for its customers and core operations.

Keep your business shipping.

That was the storyline. It didn’t come from a positioning framework or a messaging exercise. It came from sitting with two bags of bricks that had nothing obvious in common and looking for the pattern that connected them.

Positioning gives you the bricks. Something else builds the ship.

A bag of bricks is not a Millennium Falcon

In an earlier issue, I introduced the Lego metaphor as a way of describing where most companies get stuck.

Positioning produces parts: your category, your capabilities, your ICP, your competitive alternatives. Messaging takes those parts and arranges them by audience. The website version, the sales deck version, the outbound version. Both of these things are necessary. Neither of them does the thing in the middle.

A bag of Lego bricks is not the Millennium Falcon, even if every brick is the right color.

So what is the thing in the middle, exactly? What does it actually look like? This issue is my attempt to answer that specifically.

What’s in the bag

Most companies I work with have more bricks than they realize. They’ve done real work. Here’s what a full bag usually contains:

• Category definition

• Differentiated capabilities

• Value drivers

• ICP and buyer personas

• Competitive alternatives

• Proof points and case studies

• Customer research

• Product vision and roadmap

• Founder/leadership point of view

• Company mission and purpose

There are two kinds of bricks in that list. Some come from positioning and product marketing work, things like category definition, ICP, and competitive alternatives, which tend to be rigorous, researched, and defensible.

Others come from the brand side: mission, purpose, the founder’s point of view on the market. Those tend to get dismissed as fluffy. They aren’t. They’re structural. The Millennium Falcon needs these pieces too.

Listed side by side, none of it forms a narrative. It forms a reference document. That document is the raw material. The storyline still needs to be built.

What assembly looks like

1. Selection

A strong storyline leaves bricks on the table. Not every brick belongs in the build, and one of the underappreciated parts of the work is figuring out which ones those are. Companies rarely have all of the bricks above; what they have is a subset, sometimes sparse, sometimes overwhelming. Part of assembly is an inventory: what do you have, what are you actually missing, and what needs to go?

Three companies I’ve worked with illustrate how different these starting points can be.

• One had a clean ICP and persona-specific messaging that was working well for its existing segment, but needed to update its positioning for the enterprise.

• Another had sharp category positioning but was missing the context and urgency that would make its solution feel like a must-have instead of a nice-to-have.

• A third had the opposite problem: pages of AI-generated positioning documents, a genuinely sharp founder point of view, and too many ideas and messages competing for attention. The first order of business was discarding half of it before anything meaningful could surface.

Selection is not about editing. It’s a matter of judgment. And because judgment requires killing someone’s darling, assembly isn’t just a strategic exercise — it’s an exercise in human alignment.

On a sales call the other day, a Head of Revenue quipped, “We need a marriage counselor as much as we need a consultant.” She was bang on. You have to mediate the friction between the CEO, the CRO, and the Head of Product. You have to guide the executive team to a place of shared conviction so that when they announce the storyline at the all-hands, they actually embody it.

Selection shouldn’t take months, but try it rush it and the pieces will never hold together.

2. Order

Context before problem before solution before vision. Get the order wrong and the buyer builds a different thing in their head than you built on paper. The context earns the problem. The problem earns the solution. The solution earns the vision.

I like to visualize this as a flywheel because one element feeds into the next (also, I just really like flywheels). Take a MedTech company I’m working with right now. They’re selling a heart monitoring device. The context is an aging population and a looming heart valve epidemic. But a single company can’t cure human aging. If they pitch the epidemic, healthcare buyers tune out. The actual problem they solve is a diagnostic bottleneck — the massive, expensive gap between a basic hand-held ultrasound and an echocardiogram.

Their solution is a clinical-grade cardiac intelligence platform. At its core is a portable heart monitor that uses seismic technology (the same tech used for earthquakes and submarines) to measure the openings and closings of heart valves. It’s a cool gadget, but if they lead with the hardware, they get bucketed as a consumer wearable and their pricing power dies in procurement.

By placing these blocks in the exact right sequence, the product becomes the engine for their vision: changing the medical paradigm (and thus the new context) from reactive “sick care” to proactive, “Heart-Centered Healthcare.”

That’s the storyline.

Without the context, the solution is just a fancy FitBit. Without the solution, the vision is a pipe dream. Rearrange them and you’re asking the buyer to do cognitive work they won’t do, especially in an enterprise context where attention is finite and competing priorities are constant.

3. Connective tissue

The narrative language that holds the shape – the word choices, the “why now,” the point of view that makes the bricks feel inevitable together instead of arbitrary next to each other? This is the part that resists systematization.

The go-to-market leaders I speak to are currently spending a non-trivial amount of time answering one specific CEO question: “Can’t we just feed our context docs into Claude and let it figure out the story?”

The answer is no. An LLM is fundamentally incapable of this because AI is the ultimate corporate sycophant. If you feed it five conflicting executive opinions, it won’t push back, play marriage counselor, or call out the misalignment. Using AI for this work means decision fatigue multiplied by a thousand. My Claude vs. your Claude vs. Claude’s Claude (I live in French Canada. There are actually a lot of people named Claude).

You can hand off a brief to an AI tool or a freelance copywriter, and both will produce more bricks. Neither will do the build.

Assembly is curation and distillation, not content generation. That distinction matters, and it gets to why this work keeps falling through the cracks in most organizations.

Assembly is pattern-finding

The underlying skill here is pattern-finding: the ability to spot the thread between things that don’t obviously belong together.

I often describe this process as journalistic. A reporter’s job is to walk into a scene with a pile of material that doesn’t seem to cohere. Quotes that contradict each other, documents that don’t connect, the off-hand comment nobody flagged as important, the brief thing someone said in passing that turns out to be the whole story.

I brought this skill with me as I transitioned out of political journalism into content strategy, communications, product marketing and, finally, consulting. I don’t see these as separate careers but one continuous project carried into different contexts and applied to new problems.

The job is finding the thread that runs through all of it. The storyline. That’s what happened with the SaaS backup company: two segments with no obvious through-line, one simple word (shipping) that held both together and dramatically simplified their enterprise motion.

Positioning frameworks can be templatized and messaging can be generated at scale. The pattern between the bricks, the one that only exists for this company in this market at this specific moment, someone still has to find it.

Why the bricklayers don’t build

The reason this keeps going wrong in most organizations has nothing to do with effort or intent.

First, it’s a systemic issue. We are living through an era of PMMission creep. Look at the job descriptions for product marketers right now. We are asking them to own positioning, messaging, content, analyst relations, and sales enablement, all while managing product launches. You can’t expect a single team, buried under feature release schedules, to effectively own the overarching company narrative.

Second, the people who produce the bricks — PMMs, PE analysts, brand agencies — are typically trained to be comprehensive and defensible. Those qualities serve the work of building bricks well.

But assembly asks for the opposite disposition: editorial judgment, narrative instinct, a willingness to drop things that are accurate and well-researched but don’t serve the build.

Most organizations don’t have anyone in this role. So the bricks accumulate. The positioning document gets finalized and filed. The brand refresh deck gets delivered. The messaging matrix gets completed. The homepage gets updated. And the story still doesn’t travel, because nobody ever assembled it into something a buyer can hold in their head.

It’s a functional gap, not a quality problem.

You don't need more bricks

Most companies I work with that are stuck at the next revenue ceiling have already done the positioning work. Some have done it twice.

They’ve over-indexed on generating material and under-indexed on assembly. They assume that if they create enough high-quality bricks, the storyline will eventually build itself. It won’t.

Without someone making the hard decisions on what stays, what goes, and what order it all belongs in, the narrative stays fractured. The team stays siloed. Buyers stay put.

To skin the cat and win the market, you don’t need to manufacture more bricks. You just need to build the ship.

“Could we look at the sales deck with the new AI story in mind?” the CEO asked me over Slack a few weeks ago.

Every single one of their customers was under the gun to deploy AI in their contact center. Now. Because of this, what my client was selling went from a very powerful, useful tool for enterprise IT and Ops teams to an absolute necessity if those buyers wanted to keep their jobs.

“Sure.” I sent notes.

Then he was back. “Can I look at the analyst talk track? The boilerplate? The buyer’s guide? The website hero?”

By the end of the week, we had a running list of twelve core GTM assets that needed updating. The urgency of the moment meant we needed new content deployed now.

We didn’t tear up their foundational positioning and start from scratch. The problem, the solution, and the vision remained exactly the same. We simply evolved the storyline to meet the moment. And once we refreshed the storyline with that new AI angle, we went back to update all those assets so everything laddered up and communicated the exact same context.

That list of twelve assets is what it looks like when a storyline evolves with the market.

The “AI-powered” reflex

Over the last 18 months, I’ve watched most B2B tech companies do a version of the exact same thing:

They added “AI-powered” to their positioning. Slapped a sparkles emoji on their homepage. They published LinkedIn posts about their internal Claude workflows and added an “AI solutions” page to the website, as if giving the feature its own URL is the same as building a business case.

None of this is dishonest. In fact, most of it is probably true. But it’s answering a question that enterprise buyers stopped asking six months ago: What are you doing with AI?

What I keep hearing from B2B CEOs and revenue leaders is that the entry requirements have gotten tougher. Buyers aren’t just curious about AI anymore. They’re walking into conversations with top-down mandates, real timelines, and massive professional accountability.

They are far less interested in whether you have AI than in whether you understand what AI just did to their business, and their job.

The AI story most companies are telling is just a product story with AI bolted on. It doesn’t answer the question actually running through the buyer’s head:

What did AI change about my world, and how can you help me survive it?

The "Why Now" conundrum

In the first issue of this newsletter, I wrote about the “why now” — the key part of the storyline almost everyone skips.

You can have strong positioning, differentiated capabilities, and a great founder, but if you can’t articulate why this matters to the buyer right now, deals die.

An AI story is the most powerful “why now” argument B2B tech has seen since COVID (and this one isn’t going away.) Because the risk of inaction became measurable, and personal.

Your AI story doesn’t add new bricks to your storyline. It answers the question those bricks have been waiting for.

The AI mandate is real

Let’s look at that client I mentioned earlier.

They sell an observability platform to enterprise contact centers. A year ago, they were bringing an existing category into a whole new space. Our heavy lifting was educational. The storyline was about explaining what this new, hybrid category (CX Observability) was and why buyers needed it.

Then the mandate landed.

Enterprise contact center leaders stopped being asked when they would consider deploying AI agents. They started getting told to deploy them now.

The failure mode — an AI agent hallucinating on a live customer call, at scale, with the buyer’s name attached to the project — went from theoretical to a career-ending reality.

The emotional register of the problem flipped overnight. The operations leader who once had a long runway to evaluate tools now had a mandate and a launch date. They didn’t need to be educated on CX observability anymore. They needed to know everything was working before they flipped the switch on AI.

We didn’t throw out the old storyline. We just ramped up the urgency.

The new storyline: CX Observability, AI Certainty.

First, we establish that this is the thing you need to execute your AI mandate right now. Then, we unpack the “what,” the “how,” and the ROI.

Adding the AI story didn’t mean subtracting everything else they do. The platform still monitors human agents, BPOs, hardware, networks, you name it. But the urgency of the AI mandate is what opens the door to a bigger conversation, with bigger customers, and bigger stakes.

The “it’s not about AI” story

Another genre of AI story is what I call the un-AI story. You don’t need to be against AI to embrace this narrative. You just need to have a contrarian or counterintuitive take on it.

I first deployed this type of AI story when I worked at LivePerson. This was the company that literally invented live chat for customer support back in the late ‘90s. They eventually acquired their way into conversational AI and — in the midst of the ChatGPT breakthrough — LLMs. So the company wasn’t against AI by any means.

But in early 2023 we needed a story to communicate that we weren’t just following the AI trend. We were actually leading the market in our increasingly crowded Digital Customer Service category.

The reason ChatGPT and its successors had struck such a cultural nerve, we reasoned, wasn’t because of AI per se. It was because they were conversational. People could interact and even form relationships with them in a way they never could with old-school chatbots. And this was precisely what made them such a breakthrough for customer engagement.

Suddenly everyone and their uncle was talking about conversational AI, a space we had played in for years. But the real value was “not about the AI,” we declared. “It’s about the conversation.” Not the technology itself but what it enabled for enterprise customers who had long been chasing the holy trinity of automation, personalization, and scale.

This was our AI story. It took the focus off the technology and back on the outcomes we were championing.

I’m currently working with a MedTech company that has its own un-AI story. They’re selling a clinical-grade cardiac intelligence platform that intentionally eschews AI in its core heart monitoring and diagnostic technology. This makes it more accurate and reliable and, therefore, suitable for clinicians.

The company isn’t against having AI in their product. In fact, it’s building AI capabilities for non-clinical applications like reporting and analytics. But it’s decidedly not an “AI-first platform” and this is precisely what differentiates it from the consumer-grade wearable devices it gets confused for in a health tech market crowded with hype and (false) hope.

By leaning away from AI, we’re leaning into what truly makes them special.

Another kind of AI story

Not every AI story runs through the product. Sometimes, it runs entirely through the market.

I have another client in the backup and resilience space. Their CEO is extraordinarily forward-thinking about being AI-first operationally. But their product itself hadn’t materially changed, and their marketing was telling a story from 18 months ago.

The AI story we built wasn’t about new AI features. It was about what AI was doing to the environment their customers operated in.

Adding AI agents and automations to mission-critical SaaS platforms massively increases the surface area for things to go wrong. A single poorly designed automation or an AI agent gone rogue can wipe out a GitHub repo, delete years of Jira documentation, or destroy a Shopify catalog in seconds. The catastrophic downside is sudden, and it happens at scale.

You could easily build a fear-mongering narrative out of that. We went the exact opposite way. To actually reap the benefits of AI, you need the absolute assurance that a rogue automation won’t break your business.

Their AI story isn’t “we use AI.” It’s “AI increases your risk, and we provide the safety net that empowers you to deploy it anyway.” More on their storyline next issue.

A crucial distinction

This brings us to the most important distinction between company positioning and the company storyline.

Positioning stays the same unless there is a major strategic shift in the business itself. But a storyline must evolve when the context changes.

None of these companies started by asking, “How do we add AI to our story?” They started by asking, “What is AI doing to the world our buyers operate in?”

For the CX observability platform, AI created a high-stakes mandate. For the resilience company, AI increased the odds of disaster. For the cardiac intelligence platform, AI made clinical accuracy more crucial yet elusive than ever.

Looking back at that Slack thread with the 12 updated assets, it wasn’t busywork. It was evidence that the storyline had evolved to meet the new context. When the storyline is right, every container — the deck, the website, the PR boilerplate — reflects the same underlying urgency.

Most companies are still just answering, “Do we have AI?”

It’s the wrong question, and it has a very short shelf life.

There used to be this debate in the copywriting world: clear vs. clever. Should your words inspire and delight people or simply convey the right information in the most direct way?

The “clear” camp won, and they were mostly right. But the victory created a false binary that the B2B world internalized without questioning it: if people aren’t buying, you’re not being clear enough.

So companies optimized for clarity. They built clearer positioning, clearer messaging, and clearer homepages. They wrote shorter sentences using smaller words.

And it worked. Companies are clearer than ever. But they’re also losing more deals than ever to “no decision,” “let’s circle back next quarter,” and enterprise buyers who nod along enthusiastically and then settle for the “good enough” solution they’re already using.

Because it turns out clear vs. clever was the wrong question. A storyline isn’t about being clever. It’s about being believed, remembered, and trusted. Those are completely different outcomes from being understood, and clarity alone doesn’t produce any of them.

Positioning is necessary but not sufficient

The positioning frameworks that exist today are very good at what they do. Clear category, clear capabilities, clear ICP. These things are important because you can’t build a storyline on a weak foundation.

But positioning is the floor, not the ceiling. It gets you understood. It doesn’t get you believed.

The difference shows up in how deals die. Confused buyers leave early. They say, “I don’t get it,” and you never hear from them again. That’s a positioning failure, and it’s usually diagnosable.

The harder failure is the clear-but-unconvinced buyer. The one who says, “This is really interesting, let me take it back to my team,” and then goes quiet. The meeting felt great. Heads were nodding. Nothing was confusing. And then nothing happened.

That second failure is almost impossible to diagnose if you’re only looking at clarity. Because nothing was unclear. The problem lay somewhere else entirely.

The nod-and-disappear

The pattern is always the same: the call goes well. The prospect says the right things. “This is exactly what we need.” “Let me loop in IT.” “Can you send me something I can share internally?”

Then silence. Weeks of follow-ups that go nowhere. Eventually: “We’re going to push this to next quarter”.

What happened? The prospect understood the product. They even liked it. But they couldn’t walk into a room and make the case to a CFO who wasn’t on the call, because there was no narrative that made inaction feel costly. There was no urgency embedded in the storyline itself.

“We need to get our ducks in a row first” is the other version of this. What prospects are actually saying is: we have all the pieces, but we don’t know how they fit together. That’s not a reason to wait. That’s the exact problem a storyline solves. But nobody told them that. Not in a way that landed.

To be honest, I’ve seen this friction play out in my own business.

I had a great conversation with a CMO in the retail tech space the other day. They had seen my content on LinkedIn and bought into my point of view on the storyline problem: the gap between positioning and messaging that most companies miss. It seemed like they were ready to start working together tomorrow.

Then, after a few days, they got back to me with, “Let’s touch base again in a few months.” It turned out they felt they had some foundational ICP work to do before they were ready to focus on their storyline.

It stung because, in my experience, ICP definition is an active part of the storyline process, not a prerequisite. But I get it. They weren’t ready. They weren’t aligned at the executive level. They had just hired a product marketer who was invested in a certain project, with a certain outcome, on a certain timeline.

The CMO understood exactly what a storyline is and why they needed one, but the “why now” wasn’t there. Yet.

Elevating the story

When an enterprise buyer says, “I don’t get it,” most companies assume a comprehension problem. So they react predictably: simplify the deck, shorten the homepage, or twist themselves in knots trying to fit into a Gartner-approved category (or – even more perilously – try to create their own).

But “I don’t get it” almost never means “I’m confused about what your product does.” It means: I don’t understand why this matters to me, in my business, right now. That’s a context problem, not a clarity problem. And no amount of product simplification fixes a context gap. It just makes it clearer to you that the buyer still doesn’t care about something.

Let me show you what I mean.

I worked with a client in the sustainability tech space who was looking for help repositioning, given the unfortunate corporate backlash against ESG. Fixing the clarity of their positioning was just a matter of changing a couple of words. They became a “sustainability reporting platform” instead of an “ESG reporting and data management platform.”

Simpler, clearer, less controversial. But the real work was in convincing buyers this was something they needed to invest in now — not in spite of the uncertain regulatory environment, but because of it. This involved jiu-jitsuing industry headwinds into tailwinds and leaning into the context instead of away from it.

In other words, we made the regulatory uncertainty the reason to buy, not the reason to wait.

To do that, first, we needed to reframe and elevate sustainability reporting from a do-gooder environmental nice-to-have to the must-have level of financial reporting. An essential way for enterprise CFOs to safeguard the business from serious legal and reputational damage.

Once we established the mission-criticality of sustainability reporting as a discipline, it followed that sustainability leaders needed a purpose-built tool to manage this very complex, cross-functional process. This narrative naturally led to my client’s platform becoming the de facto solution, given that they were competing with general-purpose platforms that had bolted on sustainability modules, which didn’t offer anywhere near the level of efficiency or assurance (not to mention functionality).

Sure, their new positioning was clear, but it was already perfectly clear what they did and who it was for. We didn’t need to simplify their features. We needed to focus on why they mattered now more than ever. That’s where the storyline came in. By elevating sustainability as a priority within the office of the CFO (the buyer), we elevated the people doing the work (the champion). And by extension, we elevated the software they need to do their job (the category).

This “elevating sustainability” storyline became the foundation of their Series C announcement, a new enterprise-focused sales deck, and new persona-based messaging aimed at the CFO and CIO, key stakeholders in the buying committee they’d been struggling to win over. Perhaps most importantly, it became a way to rally their internal team around a positive, customer-centric story during a time of profound change and uncertainty in the market.

That’s what a storyline does that positioning alone never could.

The champion test

Let’s make the understood vs. believed distinction even more concrete.

In an enterprise deal, your champion has to sell your solution internally. You need to get through to a CFO who wasn’t on the demo, a CRO who has 15 other priorities, and a procurement committee evaluating a half dozen vendors on a spreadsheet.

If all your champion has is clarity (”we do X for companies like us, here’s how it works”), that’s a description. It gets filed under “interesting, not urgent,” which might survive one internal meeting, but not three or five.

If your champion has a storyline (”we have a problem we didn’t realize we had, it’s costing us X, the regulatory environment is about to make it worse, and this is the only vendor that gets it”), that’s a reason to act. That’s something a CFO can resonate with, and resonance is what survives the internal game of telephone.

Take the EdTech company I wrote about last issue. Unlike my sustainability client, their category was genuinely confusing. We absolutely had to clarify their positioning before tackling the storyline. But once that foundation was set, it was the storyline that gave their champion the ammunition to walk into a boardroom and say: “We have a multi-million-dollar exposure that nobody’s managing. Here’s the solution.”

That isn’t just clearer than what they had before. It’s more believable. It’s more empathetic. And it’s a hell of a lot more urgent.

What belief actually requires

Clarity answers one question: Do you understand what we do? Belief answers three harder ones:

• Do I identify with your point of view? An enterprise buyer needs to know what you see that others don’t. Clarity simply states, “Here’s what we do.” A point of view says, “here’s what everyone else is getting wrong, and here’s what we’ve learned from being inside this problem.” That is the difference between a buyer who just politely nods along and a buyer who actively leans in.

• Does this connect to my world? This isn’t about pitching your product’s general value. It’s about mapping their specific situation to your narrative and exposing why their current approach is failing them right now. While clarity describes your product, context describes their problem in a way they haven’t quite been able to articulate yet. This shows empathy and builds trust.

• What happens if I wait? Belief demands an answer to the cost of inaction. You have to point to a real shift in their market, a new competitive threat, or a looming regulatory environment that makes “let’s revisit next quarter” far riskier than moving forward.

The wrong debate

The industry spent a decade arguing clear vs. clever. But it was never about that.

It was about being believed. Remembered. Trusted. And that requires a point of view, context, and urgency. None of these things show up in a positioning deck, no matter how clear it is.

A storyline isn’t about cleverness. It’s about making your positioning believable, memorable, and transferable.

Clarity is what you need so people understand the words. A storyline is what you need so people act on them.

I was invited to a dinner party the other day. Intimate, invite-only. And part of the intro that went around to my fellow guests was that I was “someone who was doing storytelling before storytelling was cool.”

Which, fair enough. I have been.

Storytelling is definitely having a moment. The Wall Street Journal ran a piece late last year about the rise of the storyteller, and it went everywhere. LinkedIn job postings with “storyteller” in the title doubled year over year, landing somewhere north of 50,000 in marketing alone, plus another 20,000 in media and comms.

Mentions of storytelling on earnings calls hit 469 in 2025, up from 147 a decade ago. Vanta created a Head of Storytelling role paying up to $274,000. Notion merged their comms, social, and influencer teams into a single 10-person storytelling unit. Google, Microsoft, USAA, all hiring storytellers. Chime’s Director of Corporate Editorial & Storytelling posting pulled 500-plus applicants, most of them ex-journalists.

This is all documented in the WSJ piece, and I’m here for it. The attention, the investment, the executive-level recognition that story matters in business. All long overdue.

But it feels like everyone’s kind of lost the plot.

Storytelling has become shorthand for almost everything. Creative writing. Screenwriting. Stand-up comedy. Advertising. Public speaking. Content. LinkedIn posts about your dog teaching you leadership lessons. Some guy using a health scare as a hook to pitch his lead magnet.

Everyone’s talking about storytelling to the point where the word is just as meaningless as “content” became 10 or 15 years ago. I would know because I was doing content before content was cool, too.

"So, what's your story?"

There’s an age-old question we ask people when we meet them for the first time.

“What’s your story?”

When someone asks you that, they’re not looking to know where you’re from or what you do for a living. They want to know what you’re all about. What’s your point of view. What do you believe. What makes you you. How are you different from the last five people they talked to.

They want you to say something that makes them lean in. They’re really asking one question: Why should I care?

That’s what I mean when I talk about the storyline.

I use that word deliberately. A storyline implies continuity. Think Lord of the Rings. It connects across multiple books, multiple movies, multiple stories. Each one stands on its own, but the through-line is what makes you care about the whole thing.

Your business needs the same kind of thread. One that connects your sales deck to your website, to your product launches, to your content strategy, to the way a customer talks about you in a room you’ll never be in.

A story is something you tell. A storyline is something you operate from.

Most companies have plenty of stories. They’ve got the founder journey in the investor deck. They’ve got case studies on the website. They may even have a sales deck with a decent narrative arc. What they don’t have is a single coherent thread running through all of it.

Their sales team tells one story. Marketing tells another. Product tells a third. When someone asks, “Tell me about your company,” they get a different answer depending on who they ask.

That’s a storyline problem.

What a storyline actually contains

The word “story” on its own is so overloaded it’s practically meaningless. So let me break down what a storyline actually contains, because it’s specific.

A Storyline is anchored in your point of view. What do you believe about your market, your customer, and the world that others don’t? This is the quality that makes people lean in and listen. The thing you know that your competitors either don’t see or aren’t willing to say out loud. Your point of view can’t be manufactured for marketing purposes. It has to come from your actual experience building your product and serving your customers. But it’s there, and it’s yours for the telling.

A Storyline is oriented toward the future. Positioning is about what you do right now. But customers buying enterprise software, investors evaluating your Series C, partners considering an integration, they all care about where you’re going.

Your storyline captures what you do now, where you’re headed, and why people should come along for the ride. Early-stage companies where product vision outstrips actual product need this. So do enterprise companies where buyers are locked into multi-year contracts and need to know you’re thinking long term and will still be relevant and evolving quarters down the line.

A storyline is rooted in urgency. Positioning answers what you do. Storyline answers why it matters right now. And “right now” is what separates a polite nod from a signed contract. Your storyline has to connect to something happening in the buyer’s world that they can’t ignore, something that makes the status quo feel untenable. The storyline doesn’t exist in a bubble. It exists in the context of the buyer, the market, and the world.

If positioning is meant to clarify and align, the storyline is meant to educate, empathize, and inspire. It’s the crystallization of why you matter to the right people, right now.

Why messaging alone can't do this

Most people wrap story into messaging. But messaging is many things. You’ve got product messaging, sales messaging, campaign messaging, investor messaging. The messaging on your website will differ from the messaging in your paid ads, which will differ from your press release, which will differ from your sales deck. As it should. Good messaging needs to be adapted to different audiences, channels, and segments.

A storyline ladders all of that up to one thing. One consistent, overarching narrative that every piece of messaging can trace back to.

Here’s a practical way to think about it. You’re at a steak dinner. Across from you is a VP at a company you’ve been trying to close for six months. You’ve done the small talk. Kids, travel, the game last night. Now there’s a lull.

You could talk about your product, but that feels like a demo. You could ask about their challenges, but that feels like a discovery call. So you talk about the weather again and go home feeling like you missed something.

Positioning tells you what you do. It doesn’t give you anything to talk about at dinner.

Your storyline does. It’s your point of view on the market, the context your buyer is operating in, and why any of this matters, right now. It gives you a framework for those conversations. A shared language. When you have it, you lean in and say, “Hey, what’s going on with [industry shift] at your company? How are you dealing with that?” Suddenly you’re talking shop. You’ve built more trust in 90 minutes than in six months of emails.

Messaging is plural, while the storyline is singular. And most companies, even ones spending serious money on brand and positioning and go-to-market, have never actually found and articulated theirs.

The gap between positioning and messaging

When people talk about positioning, they usually bundle it with messaging. Positioning and messaging, messaging and positioning. The salt and pepper of the B2B strategy world.

Positioning tells you what you do and where you fit. It’s your category, your differentiation, your ideal customer When it’s done well (and it’s often a key step on the way to the storyline), it’s incredibly valuable. It provides focus and alignment.

And yet, most companies treat positioning and messaging as the complete picture. Positioning flows into messaging, messaging flows into content and campaigns and sales materials. Done.

But moving directly from positioning to messaging is like going from architectural blueprints straight to interior decorating. You’re skipping the thing that holds the building together. That thing is the storyline.

It’s the overarching narrative that makes your positioning compelling and gives your messaging something to anchor to. The layer that turns a collection of true statements about your company into a coherent point of view that buyers actually remember.

Let me show you what I mean.

The blindspot

I worked with an EdTech company a while back. They’d been around for decades and were highly profitable, but they’d grown primarily through M&A. They had a collection of products under different brands, no overarching go-to-market strategy, no story.

When a PE firm bought a majority stake, the urgency to scale hit fast. They needed to sell to people who didn’t already know them. Which proved to be a problem, given they’d never had to do that before. Their existing category description was a mouthful that nobody outside the industry understood.

Our first step was positioning. We repositioned them around a clearer category and a more unified platform story, one that made it obvious who they served and why they were different from the systems they integrated with.

Positioning gave us the “what.” But the storyline had to answer a harder question: Why should their buyers care about something they’d been ignoring for years?

The answer emerged when we uncovered a massive blindspot in how their buyers managed a specific part of their finances. The kind of thing that seems minor until you realize it involves millions of dollars, manual processes, and the kind of risk that makes public officials lose sleep.

Add in a regulatory environment that’s getting stricter and budgets that are getting tighter, and the urgency of eliminating that blindspot becomes clear.

Now we had our positioning and our storyline. A unified platform that eliminates a blindspot their buyers – school district CFOs – didn’t even know they had.

From there, messaging became clear. Website copy focused on agitating the blindspot problem and introducing the solution. Sales decks emphasized efficiency gains for the end users and risk mitigation for the executives signing off on the purchase. Content marketing addressed the broader regulatory and budget pressures.

Same storyline. Different messaging for different audiences and channels.

That’s the gap most companies miss. They jump straight from their positioning statement to tactical messaging without the narrative thread that connects it all together.

Positioning gives you a bag of LEGO bricks. The storyline uses those bricks to build the Millennium Falcon. You can have every raw material right (strong positioning, solid ICP, differentiated capabilities, real proof points) and still be sitting on a pile of pieces that don’t add up to anything a buyer can hold in their head.

Why "Why Now" is the part everyone skips

There’s one more piece to this, and it’s probably the most under-appreciated and important part of the whole equation.

“Why should I care” has a silent second half:

Why should I care right now?

Most companies can articulate what they do. They can explain how they’re different. But they can’t answer why any of it matters to a specific buyer in this specific moment.

That EdTech company could have said “we’re a unified platform for [their category]” forever. True statement. Clear positioning. Nobody would have argued with it.

But “you have a multi-million-dollar blindspot that’s about to blow up in your face”? That’s a reason to take a meeting this week, and book a demo tomorrow.

If you’re selling something complex –  multiple stakeholders, six-figure decisions, buying cycles that stretch to 18 months – “right now” is the difference between a deal that moves and one that sits in procurement purgatory for nine months before quietly dying.

When the “why now” is clear, the urgency lives inside the narrative itself. The cost of waiting becomes obvious. That’s what the storyline does.

What this newsletter is about

This is what I’m going to be exploring in The Storyline.

How companies build (or fail to build) the narrative layer between positioning and messaging. What happens when they get it right. What happens when they skip it. Why the gap exists in the first place and what it takes to close it.

I’ll use real examples. Companies I’ve worked with over the past 15 years. Companies everyone knows, where the storyline lessons are obvious once you know what to look for. And the occasional example from completely outside B2B tech when the lesson is too good to leave on the table.

Some issues of this newsletter will be conceptual. Some will be tactical. Some will probably make a few positioning people uncomfortable, because I play in the spaces between brand and product marketing, content and sales, strategy and execution, where the tidy frameworks tend to fall apart and the real work gets done.

All of it comes back to the same question: What’s your storyline, and is it working?