ChatGPT Can Help You Close More Deals. Here’s How

ChatGPT can be your best sales friend/coach/mentor

Dipesh Jain
4 min readApr 22, 2023
Photo by Yuyang Liu on Unsplash

I’ve spent close to 10 years in B2B sales and have closely observed how salespeople spend their time and effort and how that impacts their outcomes.

In these 10 years, I’ve worn multiple hats, starting from an inside sales rep to an enterprise account executive to a sales manager and now VP of sales. I’ve made many mistakes along the way and have seen many of my fellow sales folks make some important blunders as well.

When I look back at some of the things that pull sales performance down, I see these 3 impacting the most.

#1 Selling time vs. non-selling time

Salespeople spend way too much time doing non-sales stuff, and that, by far, has the biggest impact on their pipeline and closure.

Here is what I mean by sales vs. non-sales stuff

Non-sales activities: Doing research, attending non-relevant (especially internal) meetings, wasting time on the phone and social media, and even spending excessive time updating CRM.

Sales activities: Creating an opportunity and moving the opportunity further down the funnel to closure.

#2 Getting distracted and staying distracted

Sales is tough. Like really tough, and these days, we have a very strong solution to veer ourselves away from hard tasks — Distractions.

Today, more than ever before, It is super easy to get distracted and stay in a constant state of distraction. Salespeople fall into this trap when things aren’t going well for them.

Instead of finding ways to get a response from a non-responding customer, they’d rather spend their time doing busy work and mark that opportunity as lost.

#3 Fear of hunting and rejection

In sales, you have hunters, and you have farmers.

While both roles have their own challenges, salespeople fear hunting for new business way more than mining an existing account, and naturally so. Humans have a deep-rooted fear of rejection and uncertainty. We don’t like it when people avoid us or, worse, reject what we have to offer.

These 3 factors have an outsized impact on sales performance, and these problems are getting worse. The share of selling time in a salesperson’s life continues to go down, and sales continues to see higher than market churn rates.

How can ChatGPT help?

ChatGPT, especially GPT4, can really change the game for salespeople struggling to find their mojo.

Before going into tactics and specific prompts, I wanted to highlight 3 key areas where ChatGPT can add tremendous value.

a) Improving selling time

ChatGPT can give back salespeople some valuable selling time by automating things that are otherwise time wasters. It can do a great job at helping you craft strong prospecting pitches and follow-up emails, providing industry insights and persona triggers, summarizing transcripts to generate notes, and more.

b) Playing the role of a coach or a buddy

ChatGPT can play a role of a coach or a buddy and help you navigate through some tough and sticky situations. You can, for example, assign it the role of your buyer persona and foresee objections so that you can prepare for those. It can also help you reflect on stuck deals and suggest some paths forward.

c) Making you creative

One of the biggest value adds of ChatGPT is its ability to trigger ideas and thoughts. It can help you get creative with your prospecting (e.g., add videos or give gifts to prospects), presentation (e.g., add humor), and even customer relationship management. I have personally generated and leveraged a ton of ideas using ChatGPT.

Leveraging ChatGPT — Some best practices

a) Give specific instructions

Nothing follows the principle of garbage in and garbage out better than ChatGPT. If you give it generic instructions, do not complain about garbage responses.

Give high-quality specific prompts to get the best responses.

E.g.) Instead of “Generate an email pitch for my services”, use “Generate an email pitch for XYZ service targeted towards product directors. Make it mobile-friendly and restrict it to 150 words. Avoid using jargon and superlatives. Make it sound like a text”.

To get a list of 200+ prompts like these targeted towards sales and marketing professionals, check this guide below.

b) Train your bot

ChatGPT is probably the best learner on the earth today. Prepare it well to give you the best output. Before giving it any exercise (prompt), let it know about your company, what you do, your key differentiators, etc., so that it gives you outputs based on that info.

c) Keep iterating

First drafts can be crap. That’s okay. Keep improving the outcome. If you liked a certain section of the response, ask ChatGPT to elaborate on it. If you want to delete certain parts, let ChatGPT know. If you want to change the tone or voice, let it know. Don’t settle down for V1. Keep reiterating till you get the best output. In the process, ChatGPT will learn your preferences as well.

ChatGPT can be a real game changer if used well. To help you with the process, I’ve created a guide that will get into the details of best practices and training the bot.

It also has a list of 200+ prompts to help you get started.

You can find the guide here.

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Dipesh Jain

Musings About Sales, Productivity & Behavioral Science