September 19, 2026 | Read online
I had one of the worst sales/buyer experiences I’ve had in a long time last week, and oddly enough, it gave me some hope that AI isn’t nearly as far along as we’re all being forced to believe it is.
I debated on whether or not to name the vendor on this one, but I’m going to in the interest of continuous improvement and hope that someone out there is paying attention.
As most of you know, I pretty much built my career on/with Salesforce. Not the platform itself, even though I am and always have been a customer, but the company.
I trained every rep at Salesforce from 2010 - 2018 on prospecting skills and flew all around the world doing it.
This is the first time in 15 years that I didn’t go to Dreamforce, but when I was going, my intro/”elevator pitch” at the event, when someone would ask me what I do, was - I train Salesforce how to sell.
It was a little over the top, but it ALWAYS got people’s attention and engaged to the conversation, wanting to learn more.
I say that to let you know that I have a massive respect and appreciation for the company and its people. They truly paved the way and helped define an entire generation of Sales.
They’re a great Tech company and even better Sales company. However, I think what they’re best at is Marketing. The hype they create around their new offerings and “the future of sales” is unrivaled in the industry.
The challenge has always been the execution and follow-up from the hype. They’re notorious for launching things at Dreamforce that take years to roll out and truly integrate. Still to this day, no one at Salesforce can tell me what Einstein actually was or even did.
And that’s what brings me to one of the worst sales experiences I’ve had in a long time, and why it has oddly given me hope that AI isn’t all it’s cracked up to be.
About two weeks ago, I saw the announcement of Claudeforce with Matthew McConaughey leading the way (alright, alright, alright).
The video shows how you can do everything in the Claude interface without ever going into the Salesforce platform itself. I think this is a signal that Salesforce is giving up on the frontend UI fight and doing everything to stay relevant as the system of record for the AI tools, which is one of the only hopes for SaaS platforms moving forward in my opinion.
Regardless, I was intrigued. I have my Claude CoWork attached to Salesforce through the MCP connector, but the way they made it look on the video was way more impressive than how I was using it, and I wanted to learn more.
Since I only have 2 licenses, I don’t have a dedicated AM, or at least one that I know of, so I submitted an inquiry (i.e. “inbound lead”).
You’d think that a company that is seemingly leading the AI revolution for B2B sales would have an AI agent responding to my inquiry immediately, or even have a chatbot on their website that I could interact with and knew who I was, right? Apparently not.
More than a few hours later, I get an email from my SDR who “supports my account team” to schedule a meeting to “briefly discuss how we can further be resources to you here.”
I responded by letting her know that I wasn’t sure it was worth a meeting, since I only had two licenses, and I really only wanted to know what the main difference was between Claudeforce and how I was using Claude with the MCP connector to Salesforce already.
She didn’t even acknowledge my question, and instead pushed for a meeting with my Account Manager. I was busy the rest of the day with meetings, and didn’t check emails until the next day, when I saw 2 additional emails from her trying frantically to book this meeting with her/my AM.
When I got on the call with my AM, the first thing she said was “How can I help you?” I responded with - “Well, you can answer the one question I had in my original email.”
You know what her response was? You guessed it - “What was your question?”
Now, this has nothing to do with AI, but the SDR/AM or SDR/AE handoff has always been a massive point of frustration for me and many other clients who are forced into the Predictable Revenue sales process. I don’t have a huge issue with being handed off to other people in the process, but if I have to continue to explain myself on every call, it gets pretty frustrating pretty quickly.
I go on to explain that I really just wanted to know the difference between Claudeforce and how I’m currently using Salesforce with the MCP connector. She openly admitted that she had no idea, and that the company hadn’t really told her much about it.
Are you fucking kidding me? I get the ‘ready-fire-aim’ approach and ‘fake-it-till-you-make-it’ with product releases, but come on... NOTHING?
I don’t blame the SDR for that, though. That’s on Salesforce for not giving their reps the basic tools like, oh I don’t know…AI for instance, and information to be able to have a value-add conversation for their new offering.
She then went on to fumble around in her system to identify the fact that I had the Enterprise license of Salesforce “which was good because I needed that for Claudeforce.” Let’s ignore the fact that she should have known that before getting on the call with me for a moment.
From there, she found a video that she thought would be helpful and started playing it for me. Based on the way this is going, you probably already know what video it was. Yup, you guessed it. It was the same video with Matthew McConaughey in it that I watched that led to my inquiry in the first place.
With it being painfully obvious she didn’t have any idea about the product and no interest in asking me any type of discovery questions to understand my use case, I jumped right to the pricing question, and you probably guessed it again, she didn’t know. She told me she would have to get me the pricing later that day. I gave up and got off the call well before the 30 minutes we had scheduled.
A few hours later, I got an email from her letting me know their quoting system was down and she would get me something on Monday. I’m pretty sure it was less about their quoting system being down, and more about how she didn’t know how to quote it because it’s based on consumption instead of license fees, but whatever.
The cherry on top came on Monday when I got a DocuSign in my inbox with ZERO content. Just a quote with a price and a signature line. I’m not kidding. I thought it was one of those DocuSign scams/spam messages and had to check to see if the email address matched the one from the rep on the previous email chain with her.
That experience, as frustrating as it was, oddly gave me a little hope that AI isn’t all it’s cracked up to be, and isn’t as far along as the hype might suggest.
If it really was, then the leading B2B SaaS company, partnered with the leading AI company, with an announcement and launch as significant as this, should have an AI agent on their website that knows exactly who I am, what version of the license I have, and be able to answer any question about the product I have, including pricing.
Under no circumstances should a two-person company like me, with 2 licenses of a product from a company THAT is mostly focused on large Enterprise accounts, have to engage with multiple humans and wait 4 days to get a simple answer to a basic question (which I didn’t even get) and pricing information.
That tells me that AI is a far cry from the utopian experience promised by all the marketing hype going on right now, and how good sales reps are still more important than ever.
However, this also highlights how irrelevant sales reps are who have been taught to follow a process, check boxes, aren’t curious, and don’t care. The entire shitty experience could have been saved by a single rep who gave a shit enough to take 5 seconds to look at my account before getting on the call with me, do a little research on who I was, and ask me a few questions about my use case or why I was even interested in the product in the first place.
As a side, but related note, if you’re a small to mid-sized business looking for a CRM that isn’t overbloated, doesn’t over-promise / under-deliver, allows you to customize your experience the way you want it, and leverages AI the right way, you should check out Insightly (#sponsor). We put together an Outbound Prospecting Playbook that is filled with specific tips and processes that you can implement immediately, regardless of what CRM you’re using. Check it out and let me know what you think.
#MakeitHappen
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