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.
When I saw this reply I was excited, thinking awesome I’ve escaped, and can get this done via email!
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.
I’m an entrepreneurial marketer, recovering salesperson now heading up content and community at Reprise. Over the last 20 years I’ve almost exclusively founded software startups or was an early employee. In my spare time I love playing my guitar, learning about esoteric topics, and meditating.