4 AI Prompts to Tailor Any Pitch
Challenger-style tailoring meets 2025 technology.
Today, we’re going to look at some very practical prompts to help your reps tailor their pitch to specific industries, companies and personas. This kind of tailoring is a key part of any B2B sales process, but features prominently as one of the three core capabilities (along with teaching and taking control) of a Challenger rep.
[Ed Note: If you just want to see the damn prompts already, you can scroll down to the bottom of the article. You’ll miss some exciting table-setting though. Your loss.]
Speaking of Challenger, the response to last week’s article about The Challenger Sale wasn’t precisely enthusiastic. That email ended up with a 30% open rate vs my long-term average of 36%. I choose to blame that on my mega-boring subject line—not on some deep-seated dislike of The Challenger Sale (or, I suppose, the very concept of books themselves).
Anyway, let’s just say I learned my lesson on boring subject lines. Look for more like this in the future:
Despite the slightly chilly reception, I’m not quite done with The Challenger Sale. Last week, I looked at how to use The Challenger Sale to sell AI (aka unbranded axle grease). Now, I want to look at how to use AI to sell using The Challenger Sale.
Much of the Challenger book is devoted to showing how to get core reps to become challengers. In fact, Chapter 3 exists solely to try to convince you it’s possible.
The Challenger Selling Model is simple in theory, but complex in practice, and early adopters will attest to that. The rest of this book is dedicated to sharing proven best practices, tools, and lessons learned to help companies, commercial leaders, managers, and reps implement the Challenger Selling Model.
Dixon, Matthew; Adamson, Brent. The Challenger Sale (p. 30)
One of those best practices? Doing a bunch of organization-level work to enable the reps:
The act of delivering a teaching pitch is a skill, to be sure, but the content of a teaching pitch […] must be scalable and repeatable, and as such, must be created by the organization (in most organizations, this is the job of marketing).
The same can be said for parts of tailoring. While there is a clear role for the individual rep on the tailoring front, namely, recognizing how to modify the teaching message for different individuals across the customer organization, the organization has an important responsibility when it comes to tailoring as well.
Dixon, Matthew; Adamson, Brent. The Challenger Sale (pp. 33-34)
The authors spend a lot of time in Chapters 4 and 5 explaining how the organization can enable the teaching pitch—an area I spent a lot of time on last week. Chapter 6, however, is devoted to tailoring.
Their approach to “tailoring the message” uses 4 layers (from broadest to most narrow): industry, company, role and individual. You can see that illustrated in their handy diagram that bears a striking resemblance to the SOM/SAM/TAM circles which have occupied slide 7 of startup pitch decks since time immemorial:
The idea here is that the company (marketing, in particular) ought to at least be able to equip the rep with some tailored messaging for industry and company.
Just tweaking the basic pitch to mention a little industry jargon is only part of the solution. We need to ensure reps come to the table with context about what’s actually happening in a prospect’s industry and company—along with an understanding of how that ties back to the message they need to deliver. As the authors put it:
There are so many sources of information—and many of them free—that can aid a rep in offering, at the very least, some industry and company context to the sales pitch. […]
When a rep comes in not just with a sales pitch, but with a sense of what’s going on in that customer’s company and industry, you’ve got the beginnings of a tailored message.
Dixon, Matthew; Adamson, Brent. The Challenger Sale (pp. 110-111)
As you’ll recall, The Challenger Sale is 14 years old. This was a long time before ChatGPT. Those information sources were whatever you could find on the web in 2011 with some Google searches. And further, someone (probably in marketing) had to manually do all the research and the tailoring for each industry and company. There’s a good reason this kind of tailoring was rare back then—it was hard as hell.
In 2025, though, this is a (relative) piece of cake to compile and scale with AI. There are tools that do this (Gradient Works has some that can help) but you can do a heck of a lot with ChatGPT and some solid prompts.
Luckily I’ve found myself spending quite a bit of time writing some solid prompts lately1 so I figured I’d put that to work here. I’ve put together prompts that reps can drop into ChatGPT to make tailoring much easier regardless of what you sell. And—while it’s inspired by The Challenger Sale—this kind of tailoring is important no matter how you choose to sell.
Here are the 4 prompts:
Industry - generates industry-level tailoring, including highlighting key industry challenges and how your offering can help address those
Company - generates company-level tailoring for a specific prospect, including company-specific challenges and some ideas on how to best position your offering based on that context
Persona (Role) - generates persona-level tailoring for a role at a specific prospect, suggesting messaging for someone in that role
“Functional Bias” Card (aka Persona Battle Card) - consider this a bonus. Chapter 6 includes a brief digression on what they call “Functional Bias” cards that help tailor messaging for specific kinds of stakeholders in a specific format. This prompt takes that concept a step further and combines stakeholder and industry so you can make a quick card to look at what matters for combos like “Cybersecurity CFO”.
I opted not to include an an individual tailoring prompt because it’s rare that AI and web scraping do a lot of good for learning about an individual beyond the information that’s available on LinkedIn. Your mileage may vary depending on how public specific individuals are that you’re targeting.
Scroll to the bottom of this article to see the prompts themselves or read the next section for some instructions on how to optimize your results.
How to use these prompts
These prompts are all formatted in markdown which models understand well. You’ve probably encountered it before. If you haven’t, it’s a simple way to provide some hierarchy and structure to prompts with a few additional characters that (generally) make some approximate sense.
Just copy and paste the prompt directly into ChatGPT2. Each one contains an Inputs section (“#Inputs”) which has some data for you to enter to guide the prompt for your specific situation. Just replace the stuff inside the parentheses with information relevant to your request.
I recommend making sure the “Offering” part of the input is pretty precise. Provide detailed information about your product, your positioning and your value proposition. This is, effectively, the message that’s being “tailored” based on the other context.
Once you’ve got the prompt all teed up, there are really three ways you can run it in ChatGPT. This is because—with GPT 5—ChatGPT introduced a “router” that interprets your prompts and controls how hard the system “thinks” before it provides your answer. Here are the three levels:
Just run it directly - this will output a fast answer but it won’t do much research.
Ask the model to think harder - you can add a sentence before or after the prompt that says something like “Think carefully about this request”. When you do this, you’ll see ChatGPT output a message that says it’s thinking. The response will take a bit longer but it should search more sources and be more thorough in its response. This will take a minute or so.
Use deep research - select “Deep Research” from the “+” menu by the text entry box. When you run the prompt, it’ll ask you a few questions to clarify. Once you do that, it’ll go off and do the research. This will take several minutes. (Note: depending on your ChatGPT plan, you may only have a few of these you can run per month.)
Areas for improvement
As written, these prompts are intended for early conversations with stakeholders—before you’ve started to learn information that isn’t publicly available. It’s meant to help reps show up to their first few meetings with the context to have a differentiated, informed, conversation.
What they don’t do is incorporate facts learned through conversation—things that are captured in notes, call transcripts and other CRM data. You could pretty easily extend them to include that data as part of their inputs. It works as long as that information is fairly minimal but it pretty quickly gets dicey. Gathering and managing all the context to feed to the prompt stops looking like a ChatGPT use case and more like an actual product with RAG capability, etc.
And now, finally, the prompts. Happy tailoring!
The Prompts
Industry Tailoring
# Industry Tailoring Request
## Inputs
- Industry or Companies: (Name the industry, e.g. “healthcare IT,” or list 1–3 example companies you’re targeting)
- Our Company: (The company you work for — use this to ground the analysis in what you sell and how you position it)
- Offering: (Brief description of the product, service, or positioning you want to emphasize in your outreach)
## Objective
Produce a **concise sales-facing briefing (maximum 1 page, under 500 words)** that helps a sales rep tailor their message to prospects based on the broader industry context. Focus only on **actionable insights** that show how **Our Company** can position its **Offering** effectively for buyers in this industry.
## 1. Executive Summary
List **3 bullets only** on the most important things a rep should know about the industry right now. Highlight why these matter when tailoring a message for prospects and how **Our Company** should position its **Offering**. Keep each bullet to one sentence.
## 2. Industry Trends & Drivers
List **2–3 current developments** shaping the industry. For each, explain:
* 1 sentence on what’s happening
* 1 sentence on how Our Company should position its Offering in response
## 3. Key Challenges & Pain Points
Identify the **top 3 challenges** companies in this industry face today. For each challenge, provide:
* 1 sentence on the pain
* 1 sentence message angle for Our Company’s Offering
## 4. Buying Behavior & Decision Dynamics
Complete this table with **1-line entries only**:
| Aspect | Insight | Sales Implication for Our Company and Offering |
| :--- | :--- | :--- |
| Decision Makers | | |
| Evaluation Criteria | | |
| Sales Cycle | | |
## 5. Tailored Sales Angles
List **2–3 one-sentence message framings** that a sales rep could use when selling **Our Company’s Offering** into this industry.
## Style & Output
* **Length:** ≤500 words, 1 page maximum
* **Format:** Markdown with bullets and tables only
* **Style:** Direct, scannable, actionable. No long paragraphs.
* **Jargon:** If industry jargon or acronyms are used, briefly define them in plain language (e.g., “CAC (customer acquisition cost)”).
* **Focus:** Insights that answer “so what?” for sales reps.
* **Citations:** Provide inline markdown links only for key facts. Avoid over-citation. Company Tailoring
# Company Tailoring Request
## Inputs
- Prospect Company: (Name of the company you want to tailor your message to)
- Prospect URL: (The company’s website or LinkedIn page to ensure accurate context)
- Our Company: (The company you work for — use this to ground the analysis in what you sell and how you position it)
- Offering: (Brief description of the product, service, or positioning you want to emphasize in your outreach)
## Objective
Produce a **concise sales-facing briefing (maximum 1 page, under 500 words)** that helps a sales rep tailor their message to this specific prospect company. Focus only on **actionable insights** that show how **Our Company** can position its **Offering** effectively.
## 1. Executive Summary
Begin with **1 sentence that describes what the company does in simple terms** (industry, core business, market role).
Then list **3 bullets only** on the most important things to know about the company right now (strategy, performance, challenges). Keep these recent and relevant.
## 2. Recent Developments
List **2–3 key events from the last 12–18 months only** (e.g. product launches, funding, leadership changes, layoffs).
- Exclude events older than 18 months.
- If no relevant events are found, explicitly state **“No major developments in the last 12–18 months.”**
- For each event, add **1 sentence on the implication for how Our Company should position its Offering.**
## 3. Key Challenges & Priorities
List the **top 3 challenges or priorities** the company faces right now. For each:
* 1 sentence description of the challenge/priority
* 1 sentence message angle for how Our Company’s Offering addresses it
## 4. Tailored Sales Angles
List **2–3 one-sentence message framings** a rep could use when selling **Our Company’s Offering** to this company.
## Style & Output
* **Length:** ≤500 words, 1 page maximum
* **Format:** Markdown with bullets only
* **Style:** Direct, scannable, actionable. No long paragraphs.
* **Recency:** Do not include events or data older than 18 months unless explicitly told otherwise.
* **Jargon:** If company- or industry-specific jargon appears, define it briefly in plain language.
* **Citations:** Provide inline markdown links only for key facts. Avoid over-citation.Persona Tailoring
# Persona Tailoring Request
## Inputs
- Prospect Company: (Name of the company you want to tailor your message to)
- Prospect URL: (The company’s website or LinkedIn page to ensure accurate context)
- Persona: (The specific role you want to target, e.g. “VP of RevOps” or “CFO”)
- Our Company: (The company you work for — use this to ground the analysis in what you sell and how you position it)
- Offering: (Brief description of the product, service, or positioning you want to emphasize in your outreach)
## Objective
Produce a **concise sales-facing briefing (maximum 1 page, under 500 words)** that helps a sales rep tailor their message to this specific persona at the prospect company. Focus only on **actionable insights** that show how **Our Company** can position its **Offering** in a way that resonates with this persona’s role, responsibilities, and the company’s current situation.
## 1. Persona Overview
Begin with **1–2 sentences describing this persona’s typical responsibilities**.
Then add **1 sentence on how those responsibilities likely show up at the prospect company, based on recent context.**
## 2. Current Context at Prospect Company
List **2–3 bullets** on what’s happening at the prospect company (initiatives, changes, or challenges) that is **most relevant to this persona’s role.**
- Use only events or information from the last 12–18 months.
- If no company-specific details are available, explicitly state that before giving general role insights.
## 3. Likely Challenges & Goals
List the **top 3 challenges or goals for this persona at the prospect company.** For each:
* 1 sentence description of the challenge/goal tied to the company’s current context
* 1 sentence message angle for how Our Company’s Offering addresses it
## 4. Tailored Sales Angles
List **2–3 one-sentence message framings** a rep could use when selling **Our Company’s Offering** to this persona at the prospect company. Make them concrete, not generic.
## Style & Output
* **Length:** ≤500 words, 1 page maximum
* **Format:** Markdown with bullets only
* **Style:** Direct, scannable, actionable. No long paragraphs.
* **Recency:** Do not include events or data older than 18 months unless explicitly told otherwise.
* **Specificity:** Prioritize company-specific insights over generic role descriptions. Always link challenges/goals to the prospect company’s situation where possible.
* **Jargon:** If persona- or industry-specific jargon appears, define it briefly in plain language.
* **Citations:** Provide inline markdown links only for key facts. Avoid over-citation. Functional Bias
# Functional Bias Card Request
## Inputs
- Industry: (Name the industry, e.g., SaaS, Manufacturing, Financial Services, Healthcare)
- Stakeholder: (The specific role you want to target, e.g. “VP of RevOps” or “CFO”)
- Our Company: (The company you work for — use this to ground the analysis in what you sell and how you position it)
- Offering: (Brief description of the product, service, or positioning you want to emphasize in your outreach)
## Objective
Produce a **concise sales-facing “Functional Bias Card” (maximum 1 page, under 500 words)** that documents this stakeholder’s functional bias in the context of the given industry, modeled after *The Challenger Sale* framework. The card should highlight what this stakeholder cares about most in their role, how those priorities manifest within the industry, and how **Our Company’s Offering** can be tailored to resonate.
## 1. Desired Outcomes (Decision Criteria)
List the **top 2–3 high-level business outcomes** this stakeholder is accountable for **within the chosen industry**.
- Phrase them as **metrics-driven objectives** (e.g., “Increase gross margin,” “Accelerate recurring revenue growth”).
- Tie them to industry benchmarks or typical success measures.
## 2. Focus
Describe the **primary areas of the business** this stakeholder monitors and the **time frame** they evaluate (short-term, mid-term, long-term).
- 2–3 sentences max.
- Anchor in **industry-specific priorities** (e.g., compliance in Financial Services, cost efficiency in Manufacturing, rapid innovation in SaaS).
## 3. Concerns
List the **day-to-day worries and operational questions** this stakeholder asks in this industry context.
- 3–4 bullets phrased as **questions or fears** (e.g., “Can we meet evolving compliance standards?” “Are we deploying capital efficiently?”).
- Ensure they reflect both **role responsibilities** and **industry-specific pressures**.
## 4. Potential Values
List the **specific levers this stakeholder can pull** to improve outcomes in their industry.
- 3–4 bullets showing **where they can realize value** from a solution.
- Make these actionable, linking them to how **Our Company’s Offering** aligns with **industry context**.
## Style & Output
* **Title:** Must begin with `# Functional Bias: {Stakeholder} in {Industry}`
* **Section Headings:** Use `##` for each section
* **Length:** ≤500 words, 1 page maximum
* **Format:** Markdown with bullets and short sections (no long paragraphs)
* **Style:** Direct, scannable, actionable
* **Specificity:** Always connect outcomes, focus, and concerns to the **industry context**
* **Clarity:** If any **industry-specific jargon** is used, define it briefly in plain language
* **Positioning:** Frame all elements as **what matters to the stakeholder in this industry**, not product-centric language. Save solution mapping for the “Potential Values” section. GPT 5 is an excellent meta-prompter. Developing these prompts basically starts with explaining to ChatGPT what I want to achieve and having it provide an initial version. After that, it’s a matter of tailoring the prompt in one ChatGPT session based on the output of running the prompt in another ChatGPT session. For example, I found that these prompts kept outputting a report that was too detailed so we got real specific on the length constraints throughout the prompt. As LLMs have gotten better at instruction following, good prompts are really starting to make a huge difference. It pays off to do this kind of repeated iteration to get it right.
I’ve optimized and tested these with ChatGPT and GPT 5. I haven’t tried using them on Gemini, Claude, etc but I would imagine they’ll work reasonably well.