‼️ Your politeness is costing you profit ‼️
“I don’t want to seem pushy.”
“They already paid me.”
“I’ll offer it next time.”
Every time you skip an upsell, that’s $10–$100 left behind.
Multiply that by hundreds of projects each year, and it adds up!
The fix?
A simple message sent at the perfect moment.
I call it the “In-the-Zone Upsell” and it works because you’re offering value when clients are already invested and you’re already doing the work.
Keep reading to steal the message that converts 90%+ of the time.
🧠 What is an “In-the-Zone Upsell”?
You offer a complementary add-on 24-48 hours after work starts, while you’re deep in their project.
Here’s why the timing is everything:
✅ Client anxiety is gone (you’ve started, they trust you)
🎯 You understand their needs better than your initial brief
🔥 You’re genuinely “in the zone” with their brand voice
🤝 A small add-on now feels like the right move
The result?
Your AOV increases without chasing new clients or raising prices.
🥇 Real example: $121 → $124 AOV in 8 weeks
I tested “In-the-Zone Upsell” on Fiverr. Here’s what happened.
❌ Before:
✅ After implementing the “In-the-Zone Upsell”
That’s a $3.04 increase per order.
With 800–1,000 projects per year, that’s $2,400–$3,000 extra revenue from one message.
Prices can range from $10 to $100 per upsell… this means the profit potential is HUGE!
💬 The upsell message I send (steal this)
I send this message 24-48 hours after an order starts:
⚡ Client responses within 30-60 minutes
Then I send the discounted custom offer through the platform. Accepted. Done.
🚀 How to execute an “In-the-Zone Upsell”
Step 1: Identify your micro-upgrade
✅ Steal this: What’s one small add-on you can deliver in under 20 minutes? Think: variations, strategy notes, quick audits, short videos.
👉 Quick Growth Idea: Look at your last 10 projects. What mini-task did clients often ask for? Turn that into your upsell offer.
Step 2: Time your message
✅ Steal this: Send your upsell 24–48 hours after the order is placed.
👉 Quick Growth Idea: Use a calendar reminder to ping clients mid-project with your upsell message.
Step 3: Keep it friendly and optional
✅ Steal this: No pressure. Keep the tone casual and offer it as a bonus opportunity.
👉 Quick Growth Idea: Always start with “Everything’s coming along great…” - it lowers client defensiveness immediately.
Step 4: Track results
✅ Steal this: Record every upsell attempt. Accepted vs. ignored.
👉 Quick Growth Idea: Add an “Upsell Tracker” column in your CRM or software to track data over time.
Step 5: Refine your offer
✅ Steal this: Test different versions of the message - discount angle, urgency, or result framing.
👉 Quick Growth Idea: Try offering “quick A/B headline variations,” “bonus intro paragraph,” or “extra design options.” Find the 1 that gets consistent YESSSSS’s.
💡 Your Friday takeaway
You’re already doing the hard part: delivering great work. The “In-the-Zone Upsell” captures the value you’re creating.
Remember, every project is an upsell opportunity:
You’re already in their brand voice
You’re already in their strategy
They’re already invested
That context is currency. Use it.
TL;DR: Wait 24-48 hours after a project starts, offer a complementary add-on at a discount, frame it casually with “totally optional,” send the custom offer when they say yes. Your AOV increases without chasing new clients or doubling your workload.
See you next week 🚀
Sam
—If you enjoyed issue #15, please tap the Like button below 💙 Thank you!









Loooove it!
But I would make the trigger 24-48hrs after delivering value (not necessarily the entire work but maybe the aha moment)
Personally, if I get an upsell right after I start working with someone or a saas tool, I'll have a bad salsy impression about the company/person associating them with "thinking about themselves not the customer"
The "trust upon signing" is an assumption and usually never true in my experience.
I never thought of this before! Simple no-brainer upsells could work on service industry.
Thanks for the insight Sam 🙌