Outsmarted by AI: Rethinking My Sales Strategy

How ChatGPT made me ask smarter questions about my account plan

Last week we covered a variety of different ways you, and myself, can be using custom GPTs that can be leveraged in your day to day. It’s clear that the time intensive tasks are much less cumbersome once you start understanding prompts. The biggest takeaway however was:

What if I can use this in a way that doesn’t just apply to tasks but can help me level up my daily processes, strategies, and even challenge my thinking?

We’re not at a point where you can just create your own GPT that caters to the nuances of someone’s day to day, I’ve quite literally learned this the hard way. A few limitations I found:

• You can’t upload a library of data (ie number of files/file size limitations)

• You can’t run large workflows (everything needs to be broken up into subtasks)

• If a prompt is too long, it’ll most likely break and not provide a good output

Credit: LucasAI Insights

That said, it was largely useful in getting me to think about my account plan in 2024 through a different lens, despite limitations.

This article won’t go too deep into “prompts”. It’s clear there is room for me to improve, however, there was a lot of value out of this exercise. I set out to “level up” my thinking, which helped accomplish this. The exercise surfaced a lot of questions that helped me chart out a malleable system that I can use to work backward from my number (ideally overachieve).

Today I’ll cover:

• Prompts Used

• Questions that Surfaced from this Exercise

• What My Overall Strategy Looks Like

• Path Forward

I’ve currently been assigned new accounts going into the new year. Despite not being able to “create a GPT” for this - I was still able to find a lot of benefits.

Prompts Used

Link to the full chat here.

***Some info/numbers redacted, which is why it’s in a google doc. You’ll notice a lot of questions and ways to visualize, Hopefully this helps you play around and ask questions relevant to your role.

This was the first prompt that I used. Response was underwhelming:

I then prompted GPT to reframe the approach:

At this point I’m just riffing and just asking questions, I might have been able to prompt better. It still provided interesting output:

The items on the list that caught my eye:

• Historical Purchasing Patterns

• Budget Cycles Outside of Fiscal Year End

• Seasonal Trends

• Customer Feedback and Requests

This led me down a path of asking more questions than answers. Nevertheless it was productive in terms of how to set up my strategy.

Questions that Surfaced from this Exercise:

• What data could I find on past historical spend within an account or industry?

• Are there any trends that I can find within a specific account industry that show patterns or trends that I can map back into a quarterly cadence?

• Keyword searches for products, timing, initiatives, across closed lost or past deals that I can surface in Gong?

  • Can I upload certain transcripts (redacted) and find patterns?

Ultimately I ended up with a bucketed framework that looks like below. Yes, I used some good ol’ fashioned paper and pen:

What My Overall Strategy Looks Like

Now that I have an outline of where to find the info I’m looking for, I can layer that into the things that were obvious from the outputs above.

• Trigger Events (I’ve covered this in previous posts on emailing, earning trust, and opportunity or pain.)

• Contract Renewals/Fiscal

• Tech/Competitors

• Seasonal Trends (checking tableau/SF reports)

• Gong Calls for KW around projects/ products/ close lost opps

This will give me an outline of accounts to focus on and prioritize. I already have a general picture of what this looks like.

There’s still more to go as I get acquainted with new accounts that I’m taking on, like meeting with AM’s to discuss the nuances of each account.

Path Forward

All in all, the exercise has helped me organize my thoughts and strategy with the centerpiece being three things:

How to systematize predictable revenue

Where is the revenue that’s low hanging fruit?

What accounts to focus on/prioritize in H1 going into H2?

There’s definitely more potential once this overall strategy is fleshed out. Examples include:

• Creating a custom gpt for specific accounts (and/or a plan of attack)

• Systemizing Trends that I can reuse on a qtr by qtr basis

• How can I systematize or quickly find the additional info I need to uncover patterns that I can leverage in my sales process and outreach cadences (which are relevant)?

More to come and excited to share.

If you have questions, shoot a note to andrew@hackingsales.xyz. If you want to chat through how to think through this on your own with GPT, feel free to book some time with me.

As always, thanks for reading and see everyone next week.

-Andrew K