I had ten founder calls last week.
One pattern showed up enough times that I want to write it down before I forget what it felt like.
Almost every founder I talked to had bought something. A CRM. A dialer. A list. A piece of email tooling. Some had all four. One of them had Zoho built out, a paid dialer, VoIP, and a clean contact database and had never sent a single outbound touch. His exact words: "We have not engaged in outbound at all to date."
It was not a tooling problem. It was a no-one-actually-runs-the-plays problem.
That is the real state of outbound in May 2026 from the calls I am on. Not a software shortage. Not an AI shortage. A motion shortage.
A few more specifics from the week, anonymized
One founder had a CRM full of star-rated warm leads with no follow-up engine on them. The deals had been sitting for months. He was watching them go cold in real time and was not sure what to do about it.
Another had a list of 300-plus contacts she had built personally and never systematically worked. The contacts were warm. The motion was not there.
A third was driving around her city writing building names on a notepad because she did not have anyone to do it for her. She was running a real two-person business and trying to do the lead gen between meetings. Same problem the others had, just at an earlier stage.
A fourth had already been through two cold callers and was burned. He wanted voice samples before he would even take an interview. That is not a hiring problem. That is what untrained outbound looks like at the back end. The next vendor pays for the last vendor's mistakes.
The pattern is not the tools. It is who pulls the trigger every Monday at 7am.
If you are running a sales team and your reps have everything they need on paper but the calendar still does not move, this is probably where the leak is. Not a new tool. Not a smarter sequencer. Someone whose entire job is the actual motion.
One piece worth your time this week
Jason Lemkin published a piece on SaaStr last Tuesday titled "$254. That's What It Cost Us To Run Our AI VPs of Marketing and Customer Success Last Month."
The argument: SaaStr replaced its VP of Marketing and VP of Customer Success with two custom AI agents. Marketing agent ran at $94.51 a month. CS agent at $159.55. The headline framing is $254 against the $500K to $800K all-in cost of those two human roles at a Series C+ B2B company.
It is worth reading. It is also worth pushing back on.
Where Lemkin is right: the cost-per-task math on high-volume low-judgment work is real. Dashboard refreshes, ticket triage, content reformatting, even outbound email drafting, all of that gets cheaper with AI every quarter. I run AI inside our own stack for meeting notes sync, contact enrichment, list cleanup, and I would not go back.
Where the piece quietly skips a step: marketing and customer success are not the same job as cold calling. A VP of Marketing managing a sponsor list is not the same as the human who handles a real objection at 9:47am on a Tuesday from a CFO who is half listening and looking for an exit. The $254 number is the compute bill. It does not include the engineering time that built the agents, the prompt iteration hours, the supervisor cycles, or the cost of mistakes a human would have caught.
The "AI replaces sales" narrative has quietly jumped from "AI drafts emails" to "AI is your VP" and forgot to prove the middle step. That AI can actually hold a real conversation with a skeptical buyer and convert it. The teams I see hitting plan are still the ones with humans on the phone.
That is the read for this week.
If anything in here landed, forward it to another founder or VP of Sales who would push back on it.
Justin