Why Everyone Hates Salesforce
August 3, 2026
Except for the exec that approved it, everyone that uses Salesforce hates Salesforce.
Have you ever wondered why?
You hate it because you were the designer. It turns out you don’t know sh*t about designing software and those folks in Silicon Valley kinda earned those stock options.
I’ve seen lots of Salesforce versions over the years. My first impression is always, “That seems pretty good.” But the people that have actually been using it hate it. They have felt the frustration. The friction. The sprawl. They liked it day 1 but hated it day 2.
It turns out when dumb real estate guys design software, they design it like dumb real estate guys.
I know…because it’s exactly what I did with LoanBoss.
When I started it, design was probably the role I valued least but now I value it the most. It pulls all effort/cost to the left and saves us pain and heartache later.
Design isn't making the screens pretty, it's deciding what happens before anything gets built - how the work should flow, what gets left out, and what breaks when a user does something you didn't expect.
After five years of painful lessons, we spent over a year redesigning the entire system. I did that because customers pay us money for top quality experience, but I’m not sure I would have done that if this was strictly an internal tool. Instead, my team would be chained to a system and workflow that continued to deteriorate in the years to come.
Turns out I’m not a big believer in sunk cost fallacy when it’s my own money…
AI is tricking us into thinking we're software developers. It writes the code, so we assume the hard part is handled. But AI just made us the designer again...the same designer that built the Salesforce everyone hates…
…except this time there's no Silicon Valley engine underneath. At least Salesforce gave us real infrastructure, real security, real uptime, real data governance. Vibe coding hands us the design job AND the engineering job. It's Salesforce minus the parts that actually worked.
Here's the trap: every vibe-coded tool is, by definition, an internal tool. There are no paying customers to force the redesign. No churn risk to motivate a V2. The only people who suffer are our own teammates, and they don't get a vote.
The tool everyone loved on day 1 quietly becomes the system everyone hates by day 301. Vibe-coded software gets stuck as day 1 software...the day 2 hate always arrives, but the redesign never does. And this time, there's no Salesforce to blame because we built it ourselves.
Don’t Replicate Our Sh*tty Processes
During onboarding, one of our customers said, “Don’t replicate our sh*tty processes.” What I hadn’t considered was that they were, in part, paying us for all the trial and error expensive lessons we’ve learned over the years.
When Pensford tried to rebuild a CRM, I asked if they were really going to out HubSpot HubSpot? Think about all the lessons HubSpot has learned about CRM over the years. Part of what we’re paying them for is those lessons.
They’ve already solved a million problems that we don’t realize we’re about to uncover…why not just pay them so we can fast forward to the fun AI stuff?
I am a big believer in comparative advantage, but for some reason I feel like I need to build everything myself. I’m trying to get better and a lot of expensive lessons have made that a bit easier. The Real Boss™ would call it growth.
These lessons are ones I am trying to apply earlier in our AI projects so my team isn’t handcuffed to a cheap Salesforce knockoff that I vibecoded three years from now.