How to Revolutionize Your Outbound Sales Strategies with ChatGPT, Your Outreach Assistant


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New business challenges need new strategies and tools. One thing’s for sure: the digital world is becoming more competitive. This means that it’s getting harder for businesses to make their inbound and outbound sales strategies stand out. 

Thanks to Artificial Intelligence (AI), sales outreach efforts are leveling up! In TaskDrive’s recent webinar, Tim Cakir (CEO) dives into the world of AI-enabled sales strategies. ChatGPT also takes on a new role as an outreach assistant.

The growing influence of AI on sales

In Tim’s words, sales tasks that used to take him four hours now only take 30 minutes. If you missed the last webinar on how ChatGPT can be a sales assistant, you can catch the recap here. But that’s just the tip of the iceberg. AI actually has the potential to transform the sales landscape as a whole. 

As AI continues to advance, its influence on various industries, including sales, is becoming more prominent. Organizations are embracing AI-powered tools and technologies to drive efficiency, enhance customer experiences, and achieve better sales outcomes. 

Here are some key ways that AI is already transforming sales processes:

  1. Data-driven decision-making. AI helps sales leaders and teams by analyzing huge amounts of data. That way, organizations can gain valuable insights into their customers’ behaviors, preferences, and patterns.  
  2. Faster lead scoring. By automating the lead scoring process, sales professionals can focus on high-value opportunities while the lead scoring happens in the background.
  3. Predictive analytics. AI algorithms can analyze historical sales data, market trends, and industry updates to make accurate predictions and sales forecasts.  
  4. Automation of sales processes. As shown in the ChatGPT, Your Sales Assistant webinar, AI tools like ChatGPT can be prompted or trained to handle repetitive tasks so SDRs can focus on creating relationships with potential clients and closing deals. 

Breaking down the 5-5-5 Method

The 5-5-5 Method is one of the proven outbound sales strategies that the TaskDrive team employs. For your sales and outreach efforts to truly stand out, you must play the personalization game—and it is so much more than putting a first name or company name placeholder in an email.

Here’s how it works: Take five minutes to find five facts about someone, then take five minutes to write a message to that person. 

  • 5 minutes to research
    Research your prospects thoroughly and gather relevant information about their company, industry, hobbies, and even personality. Doing this will give you valuable insights into how you can tailor your messaging to grab their attention.
  • 5 facts
    Choose only five key facts among all those you gathered. Here’s a tip: these five facts should be easy to relate to your product or service’s value proposition. 
  • 5 minutes to write
    Spend only five minutes writing a short, concise, but personalized email or LinkedIn connection message. Keep it engaging and focused on the prospect, not you.

Where can you look for facts? Of course, the default way to do this is to Google someone’s name, but you can also check the following sources:

  • Company website and blogs
  • Social media profiles 
  • News articles and press releases
  • Industry reports
  • Video interviews or podcasts
  • G2 reviews of the prospect’s company

Remember, this research phase should only take 5 minutes. Add this to the 5 minutes you need to write a personalized email, and you’re looking at an average of 30 hyper-personalized emails per day. Yes, that is very far from how a lot of companies go about their outreach—sending about 1,000 emails a day. 

But as Tim said, we are after “quality, not quantity.” Gone are the days when “personalization” meant putting a first name placeholder in the subject line. Today, you have to dig deep and create a connection.

Walkthrough: Here’s how you can use ChatGPT to implement the 5-5-5 Method efficiently

While the 5-5-5 Method is already effective on its own, combining it with AI tools like ChatGPT can maximize progress toward growth. Tim demonstrates a step-by-step procedure on how to implement the 5-5-5 Method via ChatGPT.

Step 1: Tell ChatGPT what role you want it to play

Before anything else, you have to establish what you want ChatGPT to help you with. In the previous webinars, Tim demonstrated how he tells ChatGPT to be a sales assistant, or a copywriter specializing in writing LinkedIn bios.

In this case, here’s how you can instruct ChatGPT to be an outreach assistant:

  • Mention the role you want it to take on. (ex. As my Sales Development Representative…)
  • Brief it about what you want it to do. (ex. You will be assisting me in writing cold emails.)
  • Provide the framework you want it to follow and explain it in detail. (ex. We will be using the 5-5-5 Methodology. Here’s how it works…)

Step 2: Feed it the five facts

Before ChatGPT can help craft the outreach emails, it needs to have the necessary information—or the five facts. During the webinar, Tim demonstrated how he would go about looking for five facts about David Henzel, CEO of upcoach. 

Quick reminder: this should NOT take you more than five minutes!

Here are the five facts and pieces of information as typed into ChatGPT:

  • First fact: I found a LinkedIn post from David Henzel where he mentioned signing up for a half marathon in Bodrum. (You can also proceed to copy and paste the post itself it is lengthy.)
  • Second fact: CEO of upcoach, an online coaching platform.
  • Third fact: I found his latest blog post on time management techniques. Here is the title: 4 Proven Time management techniques you should be using
  • Fourth fact: Member of Young Entrepreneurs’ Council
  • Fifth fact: He has a coaching business called Managing Happiness. [You can also post the header on the website]

Step 3: Craft the personalized cold email

By providing ChatGPT with key details and information about the prospect, it can assist in crafting engaging and customized email messages. The AI-generated email then serves as a starting point. You can always refine and personalize down the road.

Instruct ChatGPT that you will now proceed to write the cold email. You can also include other directives and specific preferences. Don’t be afraid to go into the details—the more information that ChatGPT has, the better it can help you.

Here’s the example shown by Tim during the webinar:

“Let’s create the cold email to connect with David. I don’t want this to be sales-y. I am the CEO of TaskDrive. I love his latest blog post about time management, and his Managing Happiness course looks super interesting.”

Step 4: Polish and refine according to your preferences

Most of the time, the initial output from ChatGPT can be too long as it tries to include all relevant information. It probably won’t sound like you either. Remember, the goal of this outreach email is to establish a connection and initiate a conversation—and not to sell immediately. 

Here’s an example of ChatGPT’s first iteration:

Dear David,

I hope this message finds you well. I recently came across your LinkedIn post about the upcoming Bodrum half marathon, and I have to say, it’s always inspiring to see CEOs pushing their physical limits alongside their professional ones.

As a fellow entrepreneur, I admire the work you do at upcoach and with your coaching business, Managing Business. It’s rare to find leaders dedicated to both professional growth and personal happiness, and I appreciate the holistic approach you bring to leadership and entrepreneurship. 

Being part of the Young Entrepreneurs’ Council, I’m sure you encounter countless challenges, yet you seem to handle them with grace and efficiency, especially given your dedication to personal development as reflected on your Managing Happiness website.

I’m reaching out because I believe we share similar values in terms of personal growth, time management, and the desire to lead fulfilled lives, both personally and professionally. 

As CEO of TaskDrive, a company focused on streamlining business processes, I’m continually learning and applying new management techniques and would be thrilled to exchange ideas and learn more about your approach, especially about managing happiness. 

Would you be open to a brief conversation? I’d love to hear more about your experiences and insights, and if there’s any way we might collaborate to benefit both our networks.

Best regards, 

[Your Name]

CEO, TaskDrive

As you can see, it really is very lengthy. To optimize the prompt, you can ask ChatGPT to remove the fluff and shorten the email by at least 70%. This will make it more concise and impactful. You can simply give instructions to ChatGPT as if it was a person. You can type something like this:

Cut the fluff and shorten it by at least 70%.

Here’s the outcome as shown in the webinar:

Hi David,

Saw your Bodrum half marathon post—that’s inspiring! Your blog post on time management caught my attention too. Great content.

I’m CEO at TaskDrive and we have a shared interest in effective leadership and personal growth. I’ve also checked out Managing Happiness—an intriguing concept. 

Could we carve out some time to exchange ideas?


[Your Name]

CEO, TaskDrive

This refined version is a lot shorter and straightforward—while still injecting a personal approach. Again, you’re free to ask ChatGPT to continue refining the email based on your preferences. You can even ask it to insert some puns or jokes!

Step 5: Creating follow-ups

As with most outreach strategies, it’s normal for prospects not to reply. In this case, sales professionals will usually try to reach out via other channels (like LinkedIn) after a few days of not hearing back. If your prospect has recently posted on the platform, chances are they are active on that platform. 

During the webinar, Tim showed the audience how to prompt ChatGPT to create follow-ups. It can be something as simple as this:

Can you use two of the facts to write a short LinkedIn message?

With this prompt, ChatGPT came up with this message:

Hi David,

I recently read your insightful blog post on time management and admire the work you’re doing at upcoach. As the CEO of TaskDrive, I believe we share a common interest in leadership and personal growth. I’d appreciate the opportunity to connect and exchange ideas. 


[Your Name]

In Tim’s own words, “It’s not bad, but it’s not amazing.” Again, you can continue editing this as you see fit. As you engage in more conversations and refine your approach, you can feed the learnings and successful messaging back into ChatGPT. 

By leveraging ChatGPT’s capabilities, you can implement the 5-5-5 Method with greater efficiency. This allows you to engage with prospects in a personalized and scalable manner. However, do remember that it’s essential to strike a balance between automation and the human touch.

Practical tips and reminders for AI-powered sales outreach strategies

  • As amazing as AI is, sales teams should not be over-reliant on AI. Personalized interactions are super valuable, and AI can help you achieve these—but they can’t do it alone.
  • AI tools can assist and expedite tasks, allowing individuals to accomplish more in less time. For example, a marketing manager who is proficient in using ChatGPT can achieve tasks that would typically take several hours for another individual. 
  • AI can also help you create valuable content to support your outreach efforts. ChatGPT can convert an article or blog post into a step-by-step guide. By providing the URL of the text, ChatGPT can crawl the content and transform it into an actionable guide, showcasing the flexibility and potential applications of the tool.
  • AI tools like ChatGPT are not meant to replace human expertise but rather augment it. We do recommend adopting a mindset that embraces AI tools as assistants and capitalizing on their capabilities.
  • Treat AI as a learning tool. Analyze the responses and feedback from your outreach efforts and use that information to improve your AI model. Regularly update and fine-tune your AI prompts to align with evolving market trends and customer preferences.

Unleash the potential of ChatGPT as an outreach assistant with TaskDrive and AI Operator

In today’s sales landscape, leveraging AI technology is becoming increasingly vital. The 5-5-5 Method for example, when combined with AI-powered tools like ChatGPT, can help businesses achieve successful results.

TaskDrive specializes in sales enablement services implemented via a quality-focused approach rather than spamming prospects. To elevate our strategies, w recently launched AI Operator—AI consultancy, custom prompt engineering, and skilled virtual assistants to empower sales teams with AI expertise. 

So if you want to incorporate AI into your business processes, go ahead and schedule a free consultation. We’ll chat about your business goals and we’ll help you figure out what custom AI prompts will help. If you’re also interested in other sales enablement strategies, you can also chat with the TaskDrive team.

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