Sales AI Email Generators: Why You Need Personalization

Numbered are the days where people will turn to Chat GPT for their every sales AI (Artificial Intelligence) needs. Don’t get me wrong, Open AI built an incredibly powerful tool that changed the world, but the idea of sales-focused output being customized to you without a heavy lift on your end is almost laughable.

In almost any sales role, cold email outreach is a staple in your funnel, and a process whose importance can’t be overstated.

When you use an AI to help you generate that email, you’re essentially asking a personal assistant to research and draft that outreach on the fly.

Close, but what if you used a Sales assistant?

The specific sales training, the background, the experience helping salespeople close valuable deals… this is the future I’m proposing in the world of LLMs (Large Language Models), and email generation is the perfect entry point.

How To Use AI With Email Generation

Start with this: enter as much data as humanly possible (within compliance rules) about what you’re selling and who you’re selling to.

Note any recent context and get good at describing emotional states of all stakeholders.

Once your AI tool has a clear picture of the situation, it’ll be way more equipped to help you analyze and respond to emails.

Next, brainstorm some top-of-mind thoughts for your response. Are you for or against what they’re suggesting? Do you have a clear response, or are there pieces to circle back on? Digest your own thoughts, organize them, and lay them out in priority order for the AI.

From there, allow the software to create your first draft.

This part is INCREDIBLY important, so don’t skip it: REFINE what the LLM gives you.

What would you do if a sales associate sent you a response that needed tweaking? You wouldn’t rewrite it from there. Being the amazing leader you are, you’d tell them what’s wrong and have them fix it themselves.

Hold an advanced LLM to that same standard. It improves their knowledge of what you’re working on, and it improves your ability to design excellent prompt sequences for a complex machine. Win-win.

Lastly, make final adjustments. In this last stage, you should realistically only edit in one or two places. But make it your own: reference a joke from before, or a comment about your city’s weather or something.

Humanize it.

Then send away! Each email will be unique, but the process won’t be:

1. Compile good input data

2. Generate an email draft using the LLM

3. Refine output data

4. Humanize refined data

5. Send

A few attempts later, and you’ll be an expert!

Why A Sales-Specialized Tool?

Here’s where most AI sales tools screw up: they create tools for the every man. "Market share” this and “active users” that… for the personal side, it’s all good. But you’re a professional.

AI in 2025 can and should be customized by industry. Sales AI is no different at all.

Ironically, “traditional” AI like Salesforce and Gong don’t have any problems creating automation. In fact, they’re elite at it. Hats off to them!

But do they do a better job with their in-house LLMs than Chat GPT?

Nope. They’ve yet to successfully develop an LLM that accurately represents the desired UX of a salesperson.

The hope is that will change moving forward, and Ask-Dwight is at the cutting edge of those efforts. However, if you do choose to stick with a Chat GPT, a Claude, or another more general LLM in the field, be sure to double down on your Custom GPTs to ensure your background is organized and accessible to help you specialize.

Top AI for Writing Cold Emails

In order from most valuable to least, here are the best AI to help you out with cold emails:

• Ask-Dwight- yeah, yeah, we’re biased, but hear me out: Dwight’s directness and fully-customized sales background makes email drafts clear but polite, and uniquely tuned to salespeople’s needs for accomplishing sales tasks.

• Gong.io- also a great option! Super skilled at using your historical data to create value-adding emails.

• Lavender.ai- great for reviewing language to reduce spam folder placement. Not so good with doing the actual writing.

There you have it! These cold emails won’t be writing themselves, so consider the information laid out in this article, and if you have any questions, feel free to hit up Dwight on your way out!

LLMs For Salespeople: Turn Your AI Into An Industry Specialist

We all love a good Chat GPT, a Claude, a Gemini and, of course, the sheer MAGIC of what they’ve created. But they’ve stopped well short of the finish line. Large Language Models (“LLMs”), like other artificial intelligence (AI), SHOULD be specialized.

Not only should they be specialized, they should be uniquely GIFTED to support those specialized fields. It’s not enough to slap together a Custom GPT or Claude project. LLMs should be designed for an industry. Shaped by it over time.

Without that level of personalization, the only “shape” you’ll be in is “square.” Only dad joke in here, I promise.

How Do Common Large Language Models Specialize?

Now that I’ve said that, let me backtrack before I tell you what we’re doing with Ask-Dwight.

If you want to customize your solution, start with a custom GPT. For consistency’s sake, I’ll use Chat GPT’s vernacular for this since they’re the clear frontrunners for this technology.

With a pro plan on almost any LLM, you can create customized “instructions” for your GPT to follow. For instance, you could:

• Design a curated outfit for the day using only your wardrobe.

• Create a fully personalized workout plan to fit your diet and your exercise schedule.

• Schedule watering & other care for your interior or exterior plants around the house.

Even in business, there’s countless ways to customize large language models to work for your unique needs. Your team could use custom GPTs to:

• Rewrite sales email drafts using your language, and optimizing for a specific tone or purpose.

• Run a custom sales playbook through your LLM, to seamlessly apply vetted persuasion tactics that follow modern best practices to your communication.

• Analyze and forecast pathways to conversion for your prospects at scale and within limited time frames.

These are wide applications within a normal Custom GPT experience, although Ask-Dwight and a very few others are actually exploring the limits of these ideas to the fullest.

The reality is that very few AI companies have EXCELLED in these spaces, and when they have they’ve been unable to package and release it to the public in a way that sticks.

How Does Normal AI Specialize Better Than LLMs?

While the world of LLMs seems frozen under the spell of 5-10 big players, then a half a million smaller players, your non-LLM artificial intelligence has done an incredible job specializing!

Look at companies like Gong and Jasper, who are absolutely crushing the specialized world of AI. You have unlimited examples of specializing just from normal AI, which you can (and should) take advantage of TODAY:

• Transcribe calls automatically and summarize key points.

• Personalize your interactions with prospects given context within your CRM.

• Assess sales risk to determine if your pipeline prospects are at flight risk.

Under normal conditions, AI is unbelievably agile and able to specialize seamlessly to an industry- so what’s the missing piece?

It’s the dark, underbelly of the rock nobody wants to look under. It’s the fear of the unknown with LLMs, and how to best leverage them.

The 10 weekly calls with the Product teams, ending in a “let’s circle back next week,” and the reason these larger companies can hide behind a version 25329 release while discounting sales enablement through LLMs as “vibe coding.”

Customized LLMs are the brand-new, hot pink convertible parked in front of the school.

Get in losers. We’re customizing for our people.