Today, I was trying to upgrade from the freemium tier of a SaaS product, to a higher tier with simply more users.

Since I signed up with zero friction and started using the product, I expected the upgrade process to be as frictionless.

I was sadly mistaken.

I won’t mention the brand because it’s rude and unnecessary, but I do want to walk you through the experience.

🥊 How it went down

I got a ping from my colleague about upgrading to allow more people to use it.

The tool features a per user’ish model, so I counted how many people needed an account and was ready to buy, with my credit card in hand.

I clicked around the dashboard a bit and saw an “Upgrade My Plan” CTA, clicked on it, and was brought to a page with 3 options:

PROFESSIONAL – $19.00 Per Month

TEAM – $99.00 Per Month

ENTERPRISE – Custom Solutions Contact for Pricing

Ok, this is a basic, old school SaaS pricing model. Fine.

Then I was asked for to fill out a 2-step long web form that now apparently was to “Request a Demo”.

Ugh, I don’t need a demo. I’m already using the product and just need more seats.

I took a deep breath…and kept playing along.

Some time after submitting the form, I get an email from a sales rep that sadly looked like this:

A few issues with this email to point out:

  • He tried to call out of the blue, without notice, or idea whether I wanted to do a call or not. Who told him to call? Of course, I’m busy. Duh. I haven’t talked to my own mom in weeks 😟. But I get it. It’s an old school inbound qualification process that doesn’t take product-led data into account. Not his fault, this was his training and probably an Outreach/SalesLoft template, in a poorly designed sequence/cadence.
  • Meanwhile, the clock is ticking and my colleagues are waiting for an answer. Productivity is taking a hit.
  • He then gives me a discovery request: “I’d like to learn more about what you are looking for and help provide some recommendations.”
  • Then, he asks me for a call by giving me his calendar invite.

Ok, fine. But I don’t want or have time for a call. Let me try email.

My reply:

His reply:

When I saw this reply I was excited, thinking awesome I’ve escaped, and can get this done via email!

My reply:

BUT, Then I got this reply from him 🤮:

Huh? You’re booked up today and OOO tomorrow? But wait, I don’t even want a call. Just give me my fu%king upgrade.

At this point, I felt like moving on to another vendor, and was frustrated that I seemed to be speaking to a salesperson who wasn’t listening to me, and forcing me into a buying process that I didn’t want to be in.

I had to walk away from the email for a bit and gather my composure.

I then decided to try again and replied:

Let’s see if he gets a clue.

Hit me up on Linkedin if you wanna learn what happened next.