Here’s a simple exercise that will fundamentally change how you think about your product, your customer experience, and your go-to-market motion.
Try buying your own product. Slowly, calmly, and for real.
Not with your admin login. Not through a backdoor. Not by having your EA set it up for you.
Go through the actual buying process like a real customer would:
- Hit “Contact Me” and see what happens
- Ask Support for Help and experience the response time
- Call the Number on Your Website (if there even is one)
- Try to Upgrade In-App like a customer would
- Request to Extend Your Free Trial
You probably will be disappointed.
And that’s actually good news. Because now you know.
Why This Exercise Matters More Than You Think
I’ve been in SaaS for 20+ years now, and I can’t tell you how many founders I’ve met who have never actually gone through their own buying process. They know their product inside and out. They can demo it in their sleep. But they’ve never experienced what it’s like to be on the other side of that “Request a Demo” form.
The disconnect is real. And it’s costing you customers every single day.
What You’ll Actually Discover
When you put yourself through this exercise, here’s what typically happens:
The contact form goes into a black hole. You submitted it 3 hours ago. Nothing. No auto-response. No confirmation. No idea if anyone even saw it. Meanwhile, your competitor responded in 12 minutes.
Support is… not great. The chatbot loops you in circles. The ticket system feels like shouting into the void. The knowledge base article you need doesn’t exist, or it’s outdated, or it assumes you already know things you couldn’t possibly know yet.
That phone number? It rings 8 times and goes to a generic voicemail. Or worse, it’s disconnected. Or even worse, it’s someone’s direct line who left the company 6 months ago.
The in-app upgrade flow is broken. There’s no clear CTA. Or there are too many options. Or the pricing page doesn’t match what you see in-app. Or the checkout process requires talking to sales for a $49/month product.
The free trial extension request? Good luck finding where to even ask. And when you do, it goes to the same black hole as the contact form.
The Companies That Get This Right
The best SaaS companies I’ve worked with and invested in do this religiously. The founders at Zoom famously used Zoom for everything before it launched. The team at Slack was their own power user. Stripe’s founders went through their own integration process dozens of times.
Stewart Butterfield didn’t just build Slack. He lived in Slack. He felt every friction point. Every confusing modal. Every moment where the UX could be 2% better.
That’s the level of customer empathy we’re talking about.
The Practical Benefits (Beyond Just “Empathy”)
This isn’t just a feel-good exercise. Here’s what changes when you actually do this:
You fix conversion leaks immediately. That broken “Contact Sales” form? You’ll fix it today. That confusing pricing page? You’ll clarify it this week. Those gaps in your onboarding? You’ll fill them this quarter.
You understand why customers churn. Suddenly, those exit survey responses make sense. “Hard to use” isn’t vague anymore. You felt that exact frustration trying to upgrade your plan.
Your product roadmap shifts. The features you thought were critical? Maybe not so much. The tiny UX improvements you deprioritized? Those just became P0.
Your team gets it. When you share your experience in the all-hands, suddenly everyone understands why customer experience matters. It’s not abstract anymore. It’s real.
How to Actually Do This
Here’s the tactical playbook:
1. Create a new email address. Don’t use your work email. Use a Gmail or personal account. Be an anonymous prospect.
2. Go through every entry point. Website form, chatbot, phone number, in-app upgrade, trial extension, support ticket. Hit them all.
3. Time everything. How long until first response? How many steps in the process? How much friction at each step?
4. Document the experience. Screenshot everything. Screen record the whole thing. Take notes on every emotion you feel.
5. Compare to your top 3 competitors. Do the same exercise with their products. Where do they beat you? Where do you win?
6. Fix the top 5 issues immediately. Not next quarter. Not when engineering has bandwidth. This week.
The Reality Check Most Founders Need
Here’s the hard truth: if you wouldn’t buy your own product through your own process, why would a customer?
If your contact form frustrates you, it’s frustrating them 100x more. If your upgrade flow confuses you, they’re just going to churn instead of figuring it out.
The bar for B2B SaaS buying experiences has risen dramatically. We’re competing with the Stripes and Notions and Figmas of the world, where you can go from “interested” to “using the product” in 90 seconds. If your process takes 3 days and 4 sales calls, you’re leaving money on the table.
The Bigger Lesson
This exercise is really about one thing: customer empathy at scale.
When you’re 5 people, you know every customer. You feel their pain. You see their confusion. But when you’re 50 or 500 people, that connection gets lost. Layers build up. Processes calcify. The distance between “founder” and “customer” grows.
Buying your own product bridges that gap. It reminds you what it’s actually like to be on the other side. And that reminder is worth more than any customer survey or NPS score.
My Challenge to You
This week, go buy your own product.
Not as the CEO. Not with your company credit card. Not through the internal admin panel.
As a customer. With a personal email. Through the actual buying process.
Hit Contact Me. Ask Support for Help. Call the Number on Website. Try to Upgrade In-App. Request to Extend Your Free Trial.
You probably will be disappointed.
But that disappointment is the start of something better.
What did you discover when you tried buying your own product? I’d love to hear your stories. The good, the bad, and the “I can’t believe we’ve been doing it this way.”
