I used ChatGPT to help me write this, but I used my examples. Let me know what you think in the comments!
1. Use AI to Prepare for Complex Demos
Before any big demo or POC, we drop the customer's public website and relevant call notes into GPT and ask:
“Based on this info, what’s the best angle to show value with our platform?”
This helps my team think strategically about what to highlight and how to connect features to the customer’s pain points. It’s not replacing their expertise—it’s accelerating their thinking.
2. Roleplay Tough Questions Before Calls
I have reps ask AI to act like a skeptical CTO or InfoSec lead and throw objections their way.
“Act like a security architect and challenge me on integrating this solution.”
It helps my team sharpen their responses and anticipate what’s coming without needing to schedule a mock session with me every time.
3. Automate the Boring Stuff (But Only the Right Stuff)
We use AI to summarize call transcripts, pull out next steps, and even generate basic follow-up emails—but only for internal alignment.
“Summarize this call recording with a focus on tech pain points, integrations, and timeline.”
This saves 30-45 minutes per call and gives us a clean doc to drop into Slack or our CRM.
4. Red Team Your Own Messaging
We run our own pitch decks or technical write-ups through AI with prompts like:
“Where might a CIO find this message confusing or unconvincing?”
It’s like having a built-in devil’s advocate. One of my newer engineers flagged vague language in a key slide thanks to this trick—and it helped us win a big deal.
5. Create a Culture of Prompt Sharing
Every Friday, we share one AI prompt that worked well that week in our team Slack channel.
Example: “Summarize this integration guide into a 2-minute explanation I can give on a call.”
This simple habit has built a mini library of use cases and keeps AI top-of-mind without forcing it.
My advice: don’t wait for a formal AI strategy to get started, if you're only using it internally. Anything public, do the opposite. Start using it where it saves time or helps you think better. And coach your team to treat it like a smart assistant, not a silver bullet.
Would love to hear how others are using AI in technical sales roles. And if you have one, drop your favorite prompt below!
