4 tips to targeting enterprises as a SaaS start-up
When you're a B2B SaaS start-up, every closed-won deal is a major milestone. But when you're ready to level up and start targeting enterprises,...
Cris S. Cubero
I write for 4+ SaaS companies every week, and I use AI for most of that work. I love AI, it has allowed me to 10x my content production, but as much as it can get me surprisingly close to a finished article, it can also give me a post full of useful information that is somehow very hard to follow.
What makes AI-written content feel generic and unhelpful is the structure. AI adds useful information, but it often spreads the main answer across too many sections. These five steps fix that:
1Pick one reader and work out what they already believe about the problem.
2Turn the topic into one promise and name what kind of promise it is.
3Research the public web and your own company for evidence competitors don't have.
4Build the outline yourself, before AI drafts a single paragraph.
5Let AI draft, then add the CTA, the company section, and the SEO pass.
When AI-written content feels confusing or boring, these are the three mistakes I see most often:
1. AI mixes different audiences. One paragraph speaks to the person who would use the product, and the next speaks to the executive approving the budget. Both paragraphs may be useful, but they belong in different pieces of content.
2. It uses MY language instead of the buyer's language. Since AI has learned from my marketing materials, it makes sense that it repeats my own terminology. But buyers describe the same problem in completely different words.
3. The AI tool mixes different stages of the buying process. One section explains the basics like it's speaking to someone who has never heard of the category. The next compares vendors for someone who is already shopping. Then another section talks to someone who is almost ready to buy.
4. It buries the answer the headline promised. This is the one I see most often, and it is the reason I am writing this post. The article usually contains the information I asked for, but it arrives in pieces, spread between sections that answer different questions. 👈
Say I ask for a blog called "How to migrate off a legacy CRM" and I give the AI tool enough signal to draft it. Sometimes it gives me plenty of good information about CRM migration, but the actual migration steps are scattered throughout the article, buried under background, definitions, related ideas, and extra sections. One step appears after a definition of CRM migration, another shows up after a section about why companies delay migrations, and a few more are buried around a vendor comparison.
All of that information is useful, but the reader clicked because they wanted to know how to migrate off a legacy CRM. Now they have to find the steps and put the process together themselves, and most people just won't.
That is why so much AI content feels overwhelming even when the information is good. The answer is there, but the reader has to work too hard to find it.
Part of the problem is that AI doesn't understand your buyer as well as you do. It doesn't fully know what they care about, what they already believe and know, or what problem they are trying to solve right now.
Better prompts help, but it's YOU who have to decide, before instructing AI to draft it, what the article should actually do, who it is for, what it promises, what sections belong in it, and what order those sections should follow, because those strategic decisions determine whether the article works.
If your headline promises something to your reader, every section that follows should help you deliver that promise in an order the reader can easily follow.
Better sentences, a stronger CTA, or another AI rewrite cannot rescue an article whose structure doesn't work.
Before getting into the how-to, it helps to understand how people read blog posts.
Most people don't start at the first sentence and carefully read every word. They read the headline first, scan the subheadings, and if one of those headings looks like it answers the question in their head, they stop and read that section. If none of the headings looks useful, they leave.
That means your headings have to do a lot of work.
Search engines and LLMs also rely on the structure of the content to understand what it covers. Clear headings make it easier to see what question you are answering and how each section contributes to the answer.
Next time you're writing a piece of content with AI, show someone only your title and subheadings. Hide every paragraph, then ask them what the article is saying. If they can explain the argument back to you, the structure probably works. If they can't, keep working on the outline.
The order is key here because each step gives you what you need for the next one.
Start here every time, even if someone has already given you a headline.
You need to answer two questions:
Broad search terms can look attractive because they get a lot of traffic.
Let's use "what is CRM migration?" as an example. It may get thousands of searches, which makes it look like an obvious topic, but think about who is actually searching for it. A lot of those people may be students, junior CRM admins, people changing careers, or people who just got handed the project and are reading up on it.
If you sell an enterprise migration platform to directors of sales operations, most of those visitors may never become buyers. That's important because traffic only helps when the people arriving on the page include the kind of people you want to reach.
Before you brief AI and spend a day on the article, ask whether the person searching for the topic could realistically buy from you.
This question changes the entire article.
Imagine two directors of sales operations. The first has never seriously added up what the old CRM costs her company. Her reps complain, but nobody has put a number on it. Before she changes anything, she needs to understand why the problem is worth a budget request.
The second already knows the old CRM has to go. She has spent six months trying to plan the move without breaking her pipeline reporting halfway through the quarter. The second director doesn't need another article telling her legacy CRMs are expensive, but a practical way to run the migration.
Those two readers need completely different articles.
The first needs an explanation, and the second needs a method.
If you give the first director a detailed migration runbook, she may not care enough about the problem to open it. If you give the second director another long argument about why legacy CRMs are expensive, she will probably leave, because you are explaining something she settled six months ago.
So before you brief AI, describe your reader in one sentence. This becomes the first line of your prompt:
Who are they, and what do they already believe about this problem?
A serious buyer is rarely searching because they are casually curious. Usually, they are trying to decide something.
They may be wondering:
Those questions make excellent sections, and your company probably already has good answers to them sitting in sales calls, demos, support conversations, and customer interviews.
Senior buyers usually evaluate problems through some combination of money, time, and risk, so if you give them a statistic, explain what that statistic means for the business.
"The average CRM migration takes five months."
That may be interesting, but it doesn't tell the reader why they should care.
"Five months of migration means five months of paying for two CRM licences at once, five months of reps entering the same deal twice, and five months where nobody fully trusts the forecast. For a hundred-seat team, the duplicate licences alone are usually a six-figure line item."
Do that work for them, don't give them a number and expect them to work out why it matters.
You should decide who the reader is, what they believe, and what the problem costs them.
AI can help you find benchmarks, supporting data, and useful ways to quantify the problem.
Once you know who you are writing for, decide exactly what the article will give them.
Sometimes you start with a headline, other times you start with a general idea. Either way, you need one clear promise before you build the outline.
Let's suppose you want to write about migrating off a legacy CRM. That gives you a topic, but it doesn't yet tell you what article you are writing. Several different articles could come from that one idea. If your reader has not accepted that the old CRM is costing her anything, you might write:
Why your legacy CRM costs more than replacing it
That article owes the reader an explanation.
But if she already understands the problem and wants to fix it:
How to migrate off a legacy CRM without losing deal history
Now you owe them steps.
And if she is deciding how to resource the project:
In-house migration vs. hiring a partner: how to choose
Now you owe them a comparison and a recommendation.
If she has already committed to the migration and wants something practical:
7 things to clean up before you migrate off your legacy CRM
Now you owe them seven useful changes.
All four articles may use much of the same research, but they shouldn't have the same outline.
You ask for "an article about CRM migration" and AI tries to serve all four readers at once. It explains why the old CRM is expensive, adds a few migration steps, includes half a build-versus-buy comparison, and stops when it hits the word count. Your reader gets pieces of several answers instead of one complete answer. This is exactly how you get the article I described at the top of this post.
Ask yourself: what exactly am I promising the reader? Pay close attention to the wording. A headline that begins with "why" usually promises reasons.
For example:
Why delaying a CRM migration gets more expensive every quarter
The article needs to explain why.
A headline that begins with "how" promises a process. For example:
How to migrate off a legacy CRM without losing deal history
That reader wants steps they can follow. The subject may be the same, but the reader expects something completely different.
This is why step 1 comes first. Once you know what the reader already believes, choosing the right kind of article gets much easier.
Some headlines promise two things. If yours does, you need to deliver both.
Suppose the headline says:
Why your legacy CRM costs more than a migration, and why the gap grows every quarter
The first half promises an explanation of what the old CRM costs, and the second promises an explanation of why waiting makes that number worse. Those need separate sections. If your headline promises two things and your article only delivers one, the article feels incomplete.
Your first headline has one job, which is to remind you what the article has to accomplish. You can make it clever later. Keep that working headline until the article actually delivers on it. Then optimize it for search and make it more compelling.
Also pay attention if you suddenly want to change the headline halfway through reviewing the draft. Sometimes the headline really does need to change. But often the draft has wandered, and changing the headline simply moves the target to wherever the draft happened to end up.
You should choose the promise and stay focused on it.
AI can help you test whether the headline creates the expectation you intended.
If you clicked this headline, what would you expect the article to give you? If the answer is completely different from the article you planned, fix the mismatch before AI drafts a word.Now you know the reader and the promise. Now you need material. Research in two places because each one gives you something different.
Public research helps you understand the topic and organize the answer. Your company's own knowledge gives you examples, evidence, and language your competitors don't have.
Ask the question naturally, the way your buyer might ask it. For example:
Explain why [claim from your headline].
I want to understand this well enough to make an informed decision.Try the question in 2-3 AI assistants. Then look beyond the facts they give you. Study how they organize the answer.
Good AI answers do four things well:
That structure is useful.
When you ask an AI assistant a direct question, it usually focuses on answering you. Ask it to "write a blog post" on the same topic and it starts covering the whole subject instead. So use AI first as a research and thinking tool, then make the editorial decisions yourself.
Read your headline. Then read one proposed section heading immediately after it. Does that heading clearly respond to the headline? Repeat the test with every section. If one heading sends the article in another direction, decide whether it really belongs.
Public research only gets you so far. Your competitors can use Google, they can use the same AI assistants, they can find the same industry reports.
Your company has another source of material that they can't copy: what your customers and employees already know.
Look through:
Sales calls and demos
The objections buyers actually raise and the words they use to explain them
Win/loss and churn interviews
Why people buy, choose someone else, or leave
Messaging and positioning documents
Pains and claims your team has already spent time thinking through
Customer surveys and ICP research
Original data that nobody else can cite
Product and roadmap discussions
Why your company made certain decisions and what tradeoffs were involved
Support tickets and customer success notes
Where customers repeatedly get stuck, which makes excellent practical topics
Internal discussions
Clearer and more honest reasoning than the polished marketing version
Your existing content library
Whether you are about to write another version of an article you already have
You don't need an elaborate system. Start by getting useful calls and meetings into text. Most meeting-recording and revenue tools already create transcripts. Then put the relevant material into an AI workspace or searchable knowledge base.
Before you upload anything, clean it. Remove customer names, confidential terms, NDA-protected information, and anything else you wouldn't want appearing in a public article. Then keep the library updated so the information doesn't slowly become outdated.
Before starting a new article, you can ask:
Check our internal documents and transcripts. Find useful insights, evidence, customer language, objections, or examples related to [topic]. Also tell me whether we have already published anything that overlaps with this idea.That search can give you four useful things. First, it can give you an angle your competitors don't have. Second, it can surface evidence only your company can use. Third, it gives you the language your customers actually use. And fourth, it can stop you from publishing another version of something you already wrote.
Public research helps you make the article easy to understand. Internal research gives the reader a reason to choose your article over the ten others covering the same topic. You need both.
You decide what insight matters, what supports the argument, and what your company is comfortable publishing.
AI is useful for finding patterns across large amounts of public and internal information that no writer has time to reread before every article.
At this point you have the reader, the promise, the research, the evidence, and the buyer language. Now build the outline, and build it yourself. This is the one part of the process I don't delegate.
Write the headline and every subheading in the order they will appear, then stop. Don't ask AI to draft anything yet, and don't let it propose the order for you.
First make the headings work. I use four rules:
AI defaults to headings that act as labels. Rewrite them before you let it draft underneath.
"The cost problem" tells a scanning reader almost nothing.
"Running two CRMs in parallel doubles your licence spend for the length of the migration" lets them decide immediately whether they want the details.
That's important because many readers will only see your headings.
Order your sections so the piece explains what the current problem costs the reader, then states what you believe they should do, then shows what improves when they act. Write those three beats into your outline and AI will fill them in.
For example:
Pain: Half your reps keep their real pipeline in a spreadsheet because the old CRM is too slow, so your forecast is missing data and nobody knows how much.
Claim: Map and clean your data before you commit to a migration date.
Gain: You migrate once, and your forecast is trustworthy from the first week on the new system.
This order gives the reader a reason to care about your recommendation before you make it. Whenever possible, express the pain through money, time, or risk.
This is the most important rule in the article.
If the headline promises five reasons, your outline needs all five reasons before it moves to anything else. If it promises seven steps, all seven steps come before any background, framework, or vendor comparison.
AI breaks this rule constantly, and human writers break it for the same reason: those related ideas are genuinely interesting.
AI gives you the first reason, then a section on the root cause behind it, then a framework it knows about, then some industry context. Meanwhile the reader who came for five reasons has received one and watched the article move somewhere else.
So put the complete answer at the top of your outline and the supporting material after it. Then AI has nowhere to wander.
Readers are scanning quickly, and AI likes clever compressed headings that make them stop and decode.
"The three assumptions that go wrong" makes the reader stop and wonder which assumptions you mean.
"Why sales ops teams delay CRM migrations" or "What staying on your old CRM costs you each quarter."
Plain headings usually work better because readers understand them without stopping.
You should decide the order. That's one of the most important editorial decisions in the entire process.
Give the headline and headings to AI as a check, then make the final decision yourself.
What would a reader expect from this headline that my outline doesn't currently deliver? Which headings don't help me keep the promise?Once the outline works, hand it to AI with your reader description and your promise, and let it draft. Every section already has a clear job, so this is the fastest part of the process.
Then read what comes back against your outline rather than against your taste. You are checking whether each section still keeps the promise, not whether you like the sentences.
I leave three things until after that:
First, leave the CTA and the section about your company until the argument is finished. Both should follow naturally from what the reader just learned.
Second, save the final SEO version of the headline for later. Your working headline has been keeping the draft focused. Once the article works, optimize it for the search query and make it more compelling.
Third, add graphics and screenshots after the structure works. Visuals can make a strong article easier to understand, but they can't repair an article whose structure is confusing.
Teams often want to work in the opposite order because formatting, graphics, and CTA copy feel like visible progress. But if the outline is wrong, you are polishing something that may need to be rebuilt.
If you finish the draft and think it has wandered, give it back to your assistant and ask:
Restructure this article so it fully delivers what the headline promises. Tell me which sections don't help deliver that promise.Then decide which changes actually improve the piece.
Left to itself, AI almost always opens by describing the reader's own day back to them. You have probably seen introductions like this:
"You know how it goes. Your reps complain about the CRM, deals get logged late, and the forecast never quite matches what closes." The reader already knows this. She lived it this morning.
"If twenty of your forty reps keep their real pipeline in a spreadsheet, your forecast is missing half its data and nobody can tell you which half." Now the reader has learned something.
Tell AI to keep the opening to one or two sentences: name the problem, put a number on what it costs, then go straight into delivering what the headline promised.
Run these on your outline before you send it to AI.
If one of those answers is unclear, fix it now.
Changing an outline takes a few minutes. Rebuilding a finished article takes much longer, even with AI helping.
I have used blog posts throughout this article because they make the examples easy to see, but the basic idea applies to almost any piece of writing where the reader came looking for an answer, instruction, or decision.
The five steps stay the same. What changes is where you make the promise and what part of the piece your reader scans.
| Format | Promise lives in | Reader scans | What usually goes wrong |
| Blog post | The headline | Subheadings | Answer split across sections |
| Subject line | Subject and first line | Too much context up front | |
| Landing page | H1 and subhead | Headings and buttons | Explains instead of answering |
| Case study | Result in the title | Headings and quotes | Result buried in background |
| Sales deck | Slide titles | Slide titles | Labels like “Our Solution” |
| LinkedIn post | The opening hook | First two lines | Point lands at the very end |
| Help docs | Page title | Step headings | Concepts before the task |
| Whitepaper | Title and contents | Contents page | Findings after methodology |
Case studies make the problem especially easy to see. If the title says a customer finished their CRM migration in six weeks instead of five months, the reader wants to know how that happened. If the case study spends its first three sections describing the customer's company history, you are making the reader wait for the thing the title promised.
Help documentation works the same way. If someone opens a page called "How to connect Salesforce," they want the steps. Give them those steps before a long explanation of how integrations work.
Email is a little different because you have much less time. The subject line makes a promise, and the first sentence needs to start delivering it. That means the first two steps in this framework matter a lot in email. You still need to be clear about who the reader is and what you are promising them, and there may not be much of an outline at all.
Some writing works because the answer is deliberately delayed.
A founder story may slowly build toward a realization. A brand narrative may take the reader through a journey. An essay may work because the thinking unfolds as the reader moves through it. In those cases, the journey itself is part of what the reader came for.
The framework in this article is most useful when someone arrives because they want something specific: an answer, a process, an explanation, or help making a decision. When the reader arrives with a clear question, deliver the answer clearly and keep it easy to find.
There is one final change I would make if you manage a content team. Review earlier. Many teams wait until the writer sends a finished article. That creates a difficult situation when the structure is wrong. The manager either approves an article that doesn't really work or asks the writer to rebuild something they have already spent hours writing.
You can avoid most of that by reviewing the outline first.
The review can be very simple. Ask the writer to send you four things:
That's enough, you don't need paragraphs yet. At that stage, you can still change the structure quickly.
After writers repeat this process enough times, they will start catching these problems themselves. Then good structure becomes part of how the team writes rather than another approval step.
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