Even Rainmakers Need a Caddy When the Weather Turns

Last week, I played golf in two inches of rain.
Not my best move.

Within minutes my grips were soaked, my rangefinder fogged up, and every yardage had changed thanks to the wind and water.

My focus? Gone.
My confidence? Dampened.

That’s when it hit me — a great caddy would’ve made all the difference.

Someone quietly doing the little things: keeping the clubs dry, checking the yardage, reading the greens, and offering calm advice when things got tough.

And then, like most things I experience on the golf course, my mind turned to sales.

When It’s Already Raining in Sales

We love talking about making it rain in sales — but what about when it’s already raining?

When deals stall.
When markets tighten.
When buyers go quiet.

That’s when even the best rainmakers can lose their rhythm.

The forecast changes, and suddenly confidence, clarity, and composure start to slip.

And this is exactly where sales teams need support — not more noise, not another tool, but a caddy.

Someone (or something) in your corner helping you navigate the elements of complex selling.

What a Sales Caddy Really Does

A great caddy doesn’t swing the club for you.
They help you make better decisions, faster — under pressure.

Here’s what that looks like in sales:

💬 Keeps your confidence dry — Reminds you what’s working and where momentum still exists when the market feels tough.
📉 Reads the greens — Surfaces subtle buyer signals or risks before they turn into lost deals.
📄 Carries the right club — Pulls the perfect case study, message, or proof point for the next conversation.
🧭 Re-checks the yardage — Gives you perspective on what to do next in complex, multi-threaded deals.
☕️ Keeps the energy up — Handles the heavy admin — RFPs, follow-ups, summaries — so you can focus on the big shots.

That’s not just poetic language.
It’s a job description — for AI.

The Rise of the Digital Sales Caddy

At Kaddi, we’re building exactly that: a digital twin for your sales process.

Trained on your own content and methodology, it acts as a quiet, capable teammate — showing up at every step of the deal with what your reps need most:

✅ A summary of the last meeting
✅ A smart draft for the next email
✅ A buyer sentiment check from recent transcripts
✅ A clear view of risks and next-best actions

Think of it as a caddy for when the forecast isn’t perfect — not replacing skill, but sharpening it.

In a world where AI promises are everywhere, we’re focused on something practical:
Helping sales teams execute better, faster, and more consistently — rain or shine.

Staying Dry in Tough Weather

If you’re in a market where the forecast looks a little grey, here’s something to help:

📘 10 Prompts for Tough Weather - A quick download of actionable ways to “stay dry” and stay focused when deals start to drag.

Because even rainmakers perform better with a great caddy by their side.