How to set up ChatGPT for sales in 15 minutes

Who this is for: Account executives, sales reps, and sales teams who want to use ChatGPT for the day-to-day work of managing and closing deals.

What you'll walk away with: ChatGPT configured to know your deals, your buyers, and how you sell, plus a set of ChatGPT prompts for sales you can run every day — pre-call prep, follow-ups, pipeline reviews, and more.

Time required: About 15 minutes to run the setup, plus 10–15 minutes to connect your tools. Ongoing use takes minutes per task.

Why most sales reps aren't getting value from AI

Most sales teams that have tried AI and written it off made the same mistake: they opened ChatGPT, typed a vague request, got generic output, and decided it wasn't useful.

The AI isn't the problem. The problem is that it has no context about you.

ChatGPT doesn't know anything about you unless you give it that context. It doesn't know you sell to VP-level buyers at mid-market SaaS companies. It doesn't know you're direct in your emails and skip the preamble. It doesn't know deal X has been stuck for three weeks because the champion changed roles. It doesn't know your company's positioning against your main competitor, or that you never discount in a first negotiation conversation.

When you ask ChatGPT to "draft a follow-up email after a discovery call," it fills in all of those blanks with generic sales language, because it has no other option. The result sounds like it came from a template — because it did.

The fix requires effort upfront: give ChatGPT the context it needs. Your product, your buyers, your voice, your deals, your rules. Do that once, save it to a project, and every interaction after that starts from a foundation of actual context.
‍

What ChatGPT needs to know before it can help you sell

There are four categories of context that separate generic AI output from output that's actually usable.

1. Your tools

Your CRM, your call recorder, your email, your calendar. These are where your deal reality lives. When ChatGPT can read your pipeline, your call recordings, and your sent emails, it already knows more about your active deals than if you'd spent an hour briefing it yourself. Without tool access, you're constantly pasting context in manually. With it, ChatGPT can pull what it needs on its own.

2. Your business and buyers

What do you sell? Who buys it? What title signs the deal? What makes a good account versus a bad one? Where do deals usually stall?

ChatGPT doesn't know your company. It might have general knowledge about your industry, but it doesn't know your specific value props, your ICP, your pricing structure, or the objections that come up in 80% of your deals. You need to give it that context.

The more specific, the better. "We sell to VP of Sales at B2B SaaS companies with 100–500 employees. Deals typically involve an IT sign-off, and they stall most often when we don't have a champion who can get budget approved internally. Average sales cycle is 45 days." That's far more useful than "we sell to sales leaders."

3. Your voice

ChatGPT can write an email for you, but if it doesn't sound like you, you'll rewrite half of it anyway. Which defeats the point.

Your voice includes: whether you're formal or casual, whether you use short sentences or longer ones, whether you lead with a question or a statement, how you handle the "just checking in" moment, whether you use bullets in emails or write in paragraphs, how direct you are about next steps, even how you punctuate.

The best way to establish your voice is to give ChatGPT examples of your actual emails. Let it learn from what you've already written, rather than trying to describe it abstractly.

4. Your rules

Every experienced rep has figured out a set of moves they always make and traps they've learned to avoid. ChatGPT needs to know these.

Examples:

• "I never send a pricing email without first having a verbal conversation about budget"
• "I always offer two next-step options, not one"
• "When competitors come up, I acknowledge them and pivot to our specific strength. I don't trash talk."
• "I never send a one-line email. Every message has context and a clear ask."

Rules like these take years to develop. Once ChatGPT knows them, it applies them automatically.

The tools you'll need

Required:

• ChatGPT Plus or Team ($20/month): the free plan doesn't support Projects, Skills, or scheduled tasks

Highly recommended:

• Your CRM (HubSpot, Salesforce, Attio, etc.): so ChatGPT can read your pipeline and deal history
• A call recorder (Grain, Gong, Fireflies, Fathom, etc.): so ChatGPT can pull directly from your call transcripts
• Email (Gmail or Outlook): so ChatGPT can reference your email history and learn your writing style
• Calendar (Google Calendar or Outlook): enables automatic pre-call prep before meetings

Optional:

• Voice dictation tools: especially useful during setup, when you're answering a lot of profile questions. Wispr Flow is the one we recommend. Superwhisper and Monologue are solid alternatives. Talking through your answers is faster than typing them.

The more context you add, the more personal and specific ChatGPT's outputs will be.

Step-by-step setup

Step 1: Get ChatGPT Plus (or Team)

Go to chat.openai.com and upgrade to Plus or Team if you haven't already. The free plan doesn't support Projects or Skills, which are both required for this setup.

Step 2: Install Arrows Sales Skills

Arrows Sales Skills is a free toolkit that gives ChatGPT a set of pre-built sales workflows and walks you through a setup process that teaches ChatGPT how you sell.

To install:

1. Go to GitHub and download the SKILL.md file for each skill you want to add. (Click into the skill file at the top of the page, click on SKILL.md, and click on "Download raw file")

2. In ChatGPT, go to your Settings → Skills → New skill → Upload from your computer

3. Upload the SKILL.md file to make the Arrows skill available.

This takes under a minute.

Step 3: Create your "My Deals" project

In ChatGPT, a Project is a dedicated workspace that holds your custom instructions and runs with that context every time you open a conversation inside it. Think of it as a version of ChatGPT that already knows who you are before you type a word.

To create one: go to the sidebar, click New Project, and name it "My Deals." You'll add your custom instructions in Step 5, once the setup is complete.

Every conversation you open inside this project will automatically have your sales profile, your voice, your rules, and your deal context loaded. You never have to re-explain yourself.

Step 4: Build your sales profile

Open a conversation inside your My Deals project and run the "Arrows setup" skill.

💡 Tip: If you have a voice dictation tool like Wispr Flow installed, use it now. The setup asks several detailed questions. Talking through your answers is faster than typing them, and you'll want to be as detailed as possible.

The setup walks through four phases:

Tool check. First it confirms which tools you have connected and what data it has to work with. The more tools connected, the richer the profile.

Data scan. This is where it does the real work. It scans your CRM deals, call recordings, and email history to learn how you sell: what kinds of accounts you work, what titles you talk to, how you structure your emails, where deals tend to stall. This takes a few minutes. Let it run.

Four question sections. After the scan, it asks four sets of questions to fill in anything it couldn't pull from your data:

• Step 1: Your product, buyers, and positioning
• Step 2: Your voice and writing style — it shows you what it found and you confirm or correct
• Step 3: Your competitors
• Step 4: What you do best, and the moves that work for you

Plan on 10–15 minutes here. Be specific. The more detail you put in, the better the output.

Your complete sales profile. At the end, you get a full written profile covering who you are as a communicator, what you sell, your typical buyer, your rules, and what you want ChatGPT to handle.

Read through it when it's done. If something sounds off, correct it right there. Getting this right upfront pays off in every interaction after.

Step 5: Add your profile to your project instructions

Copy the full output from the Arrows setup. Go to your My Deals project → Project settings → Instructions, paste the profile in, and save.

That's your baseline. Every new conversation you open inside this project now starts with all of that context loaded.

You can add more on top of what the setup generates: specific talk tracks, pricing or discount policies, the names of your internal teammates, anything the setup missed. Edit the instructions as things change.

‍

Daily workflows (ChatGPT prompts for sales)

Once your project is set up, here's how to use ChatGPT for the actual work of selling. Each workflow below is triggered with a single prompt. Run them inside your My Deals project so ChatGPT already has your context before you start.

‍

Pre-call prep

Use this before any meeting with a buyer: discovery calls, demos, check-ins, negotiation conversations.

ChatGPT pulls the deal history from your CRM, relevant emails, prior call notes or transcripts, and attendee backgrounds, and turns it into a brief you can read in under a minute.

Run it with:

"Run the Arrows meeting prep for [Company]"

A good pre-call brief covers the company snapshot, who you're meeting and their role in the deal, what's happened in the conversation so far, open questions you haven't asked yet, recent company news worth referencing, a suggested agenda, and objections likely to come up.

💡 Tip: Even when you know the account well, pre-call prep surfaces things you might have forgotten — a question the champion raised two calls ago, a commitment you made that hasn't been followed up on yet.

‍

Post-call follow-up

Use this right after a call, while the conversation is fresh.

Run it with:

"Run my Arrows post-call on [Company]"

ChatGPT pulls your call recording, CRM record, and email history to generate three things: a follow-up email draft in your voice, a copyable CRM note, and relevant resources to send the buyer. It will confirm which call before generating anything. If you don't have a call recorder connected, it will ask you to paste the transcript or notes.

A good follow-up opens with something specific from the call, makes next steps explicit and time-bound, and ends with a single clear ask.

💡 Tip: If the first draft isn't right, don't start over. Tell ChatGPT what to fix:

"Make it shorter. The opening feels too formal. Add a line about the integration timeline."

One round of feedback usually gets it there.

‍

Daily brief

Use this at the start of the day when you want to know where to focus.

Run it with:

"Run my Arrows daily brief"

ChatGPT pulls your calendar, CRM, call recordings, and email to give you a full picture of your day: every meeting with attendee backgrounds, pipeline alerts, and messages that need a reply.
‍

Weekly pipeline review

Use this before your weekly 1:1 or forecast call with your manager.

Run it with:

"Run the Arrows weekly pipeline review"

ChatGPT scans your active pipeline and generates a deal-by-deal status report organized by stage: what's closing this week, what's at risk, and what needs action.

💡 Tip: After the output, ask ChatGPT to help you prep for the deals your manager is likely to ask about:

"My manager is going to ask about [Deal Name]. Help me articulate where it stands and what I'm doing to move it."

‍

Stalled deal nudge

Use this when a deal has gone quiet and you're not sure how to re-engage without being annoying.

Run it with:

"Run the Arrows deal nudge"

ChatGPT reviews the deal history across your CRM, call recordings, and email, picks a specific play based on what the data supports, and drafts a personalized re-engagement message. It won't manufacture a nudge if there's no real signal to work with.

‍

Common mistakes that kill the output

Skipping the context setup. The single most common one. If you haven't given ChatGPT your product, your buyers, your voice, and your rules, the output will be generic. No amount of clever prompting fixes a missing foundation.

Not giving ChatGPT your actual emails. Most people describe their writing style in the abstract. That's harder for ChatGPT to work from than just reading ten emails you've actually sent. Paste examples into your project instructions.

Treating the first draft as final. ChatGPT's first draft is a starting point. If something's off, tell it what to change. One round of feedback usually gets it where you want it.

Using it occasionally instead of daily. The value compounds. Reps who start every morning with the Arrows Daily Brief and draft follow-ups right after every call get dramatically more out of it than reps who remember it exists once a week.

Not updating your project instructions. Your deals change. Your messaging changes. Your competitors change. Keep your instructions current.

‍

Frequently asked questions

Can I use this if I'm on the free version of ChatGPT?The free plan doesn't support Projects or Skills, both of which are required for this setup. ChatGPT Plus ($20/month) is what you need.

Does this work with any CRM? It works with any CRM you can connect during the setup. HubSpot, Salesforce, Pipedrive, and others are supported. If yours isn't listed, you can still paste deal context manually into conversations. More work, but the outputs are still good.

Is my deal data safe when I use this? OpenAI doesn't use your data to train their models when you're on a Plus or Team plan with the data controls turned on (they're on by default). If your company has specific data security requirements, check with your IT team before connecting your tools.

Can my whole team use the same setup?Yes, but each rep should have their own project. Your project is specific to you: your voice, your deals, your rules. What the team shares is the Arrows Sales Skills file, which gives everyone access to the same workflows. The workflows are consistent; the context they run with is personal to each rep.

How long does the setup take? About 15 minutes for the Arrows setup itself. The biggest variable is getting your tools connected. If you need IT or admin approval to connect your CRM or call recorder, that can add time. Once everything is connected and your project instructions are saved, the daily workflows take 2–5 minutes each.

What if ChatGPT doesn't know something about my deal? Add it in the conversation. ChatGPT uses whatever context you provide, even if it's just pasted in. For recurring gaps, add it to your project instructions.

What if my buyers can tell I'm using AI? If your instructions are good, they probably won't. The point of including your actual emails in your project instructions is that ChatGPT learns to match your style and stops producing generic output.

I already use Claude. How is this different? The setup process is nearly identical, and the Arrows Sales Skills workflows work the same way on both. The main difference is how context is stored: Claude uses Projects, ChatGPT uses Projects with custom instructions. If you're already set up on Claude, you can copy your seller profile and paste it into your ChatGPT project instructions. You don't have to start from scratch.

‍

What to do right now

1. Upgrade to ChatGPT Plus at chat.openai.com if you haven't already
2. Download the Arrows Sales Skills file from GitHub
3. Install the skill in ChatGPT: Go to workspace settings → Skills → New skill → Upload
4. Create a project and name it "My Deals"
5. Open a conversation in your project and run: "Arrows setup"
6. Go through all the steps, and paste the output into your project instructions
7. Run your first pre-call prep before your next meeting

After that: use it daily. The reps who get the most out of ChatGPT are the ones using it for the work they were going to do anyway.