Using ChatGPT to Personalize LinkedIn Outreach at Scale

Brynne Tillman, CEO, LinkedIn Whisperer, Social Sales Link

An animated square logo for LinkedIn.

With ever-evolving sales trends, staying ahead of the curve is vital for success. The introduction of AI has not only transformed the way early adopters operate their businesses but also how they engage with clients, prospects, and other stakeholders. For example, ChatGPT – an AI-powered language model developed by OpenAI – is reshaping the sales landscape, particularly in LinkedIn and email outreach.

The key to effective sales outreach is personalization. Connecting and engaging with prospects based on what matters to them leads to trust-based conversations without being salesy. ChatGPT has emerged as a powerful tool, enabling sales professionals to craft highly personalized messages at scale. On LinkedIn, ChatGPT can help draft introductory messages tailored to the recipient’s background, interests, shared connections, content they have shared, and current role. This level of personalization goes beyond mere customization; it demonstrates a genuine effort to learn about the prospect personally.

A key mindset here is to detach from what that prospect is worth to you and attach to what you are worth to the prospect.

In the following examples, you will see that I use the word “VARIABLE”; these are where you would add the individual content. Most of the time it is a copy and paste, but you are welcome to type anything in the VARIABLE to improve the prompt.

Let’s start with personalizing a connection request.

ChatGPT Prompt Example

Write a 250-character (including spaces) LinkedIn connection request that offers value to:

  • (VARIABLE: name) Esteban
  • (VARIABLE: Headline or Title) a Supply Chain & Logistics Professional at
  • (VARIABLE: Company Name) A.P. Moller – Maersk, an integrated transport and logistics company
  • (VARIABLE: About Section or Company Page Description) going all the way together for our customers and society. ALL THE WAY is our commitment to connect the world so that everyone has both the possibility and the ability to trade, grow, and thrive. The company employs roughly 110.,000 employees across operations in 130 countries.
  • Do not mention what I do.

ChatGPT Response

Hi Esteban, Your insights in global logistics intrigue me. Let’s connect to exchange thoughts on industry trends. Your perspective is valued. Best, [Your Name].

Next, let’s take a look at engaging them beyond the connection by sharing resources that are meaningful to them.

ChatGPT prompt example:

 I am a sales rep who sells innovative CRM software to enterprise companies in the manufacturing, supply chain, and logistics space. I would like to create a LinkedIn message to 1st-degree connections that engage them in meaningful conversation and is not salesy. They do not have any content to engage on or mention. Please include a variable that offers a link to content I have curated that will be relevant to the prospect. Keep it short, and don’t pitch what I do.

ChatGPT response:

Hi [First Name],

I trust you’re doing well. Given your expertise in manufacturing, supply chain, and logistics, I thought you might find this content interesting. It’s a quick read on how technology is reshaping the industry (VARIABLE: Title of Article or Podcast):

[Insert Curated Content Link]

I’d love to hear your take on these insights. In your view, what key shifts are you observing?  (VARIABLE: Ask a question that aligns with the content). Your perspective is always appreciated.


[Your Name]

If you sell (or lead a team that does), it is essential to be an early adopter and embrace ChatGPT to get or even maintain a competitive advantage. This isn’t a fad or a trend, and, if you don’t leverage it now, it is like hesitating to get a Website or email in 1999!

To learn more about LinkedIn and ChatGPT, join our community and complimentary library at

Headshot of Brynne Tillman

Today’s blog post is by Brynne Tillman. She is CEO, LinkedIn Whisperer, Social Sales Link.