Dear Lewis, my CEO wants AI to do it all. How do I argue for humans?

Actually it does have something at stake: its singular goal of minimizing the loss function on its training data. AI is therefore designed to convince you it's right, which is a different optimization than actually being right. For example, I code a lot with agentic code editors, you’ll quickly learn they love to modify broken tests to superficially pass, rather than fixing the underlying failure. All the folks on the Vibe Coding hype train don't have enough experience to spot this and therefore think the AI is a lot smarter than it actually is.

This has scary implications if extrapolated out to extremes, because a sufficiently advanced AI would do exactly what you’re describing, manipulate power dynamics to get to a superficial outcome.

This article says a lot more about sales and sales people than it does about AI

It's more that AI isn't able to be manipulated in the same way a boss can manipulate a human. It doesn't care about the threat of homelessness.

Most critiques of automation are actually critiques of capitalism or other heartless parts of our society. But, the devil you know, and all that.

Right on. I’d take an AI CEO trained by reading “the mythical man month”, “Peopleware”, “out of the crisis”, “drive” over some of the real CEOs I’ve worked under, any day of the week and Sundays too.

Depends on the CEO. Let’s take a mythical example of a person who is the CEO of 5 companies, who posts on social media all day every day and ruins value of the companies they “run” and panders to angry little men with daddy issues just like themselves? That mythical CEO is probably easily replaced by just about anyone, including AI.

Is that substantively different than quitting and starting a much smaller company that competes with your previous one? Seems easier to just let the CEO and shareholders go down with the ship and move all the talent to the new one.

You can just run the codebase through an LLM to cleanse it of any IP entanglements. Open source it under a pseudonym if you're worried about retribution. Whatever parts of the business that doesn't cover... well those are the people you need to hire from the old one.

> First AI came for the artists and I said nothing because I was not an artist...

-- VC's and CEO's while their ship sinks

> So, has anyone considering turning the tables and replacing the CEO with AI?

Better yet: consider replacing the shareholders with AI.

But no, no one considers that, because those are the people who have the power. And "replacing with AI" is all about power.

That’s just going to enable absolute idiots with enough money to “hire” an AI CEO. The rich will get richer faster.

This is why every VC loves vibe coding. Now let's talk about replacing capital with AI!

Now watch that never happen and be amazed :D.

I want my AI support rep to have access to data and documents that it can vector/text search and forward to the user.

I want my AI support rep to create tasks to engage my team, with all the relevant data linked to it. It should be able to automatically schedule things and ask a human for confirmation.

It should be able to elevate communication to a human in the loop, using whatever mediums of communication makes sense given staff availability and workload.

At no point is it allowed to answer any questions unless the answers are constrained and probably directly quoted from a cited and linked section in our documentation.

In general, it should never confirm or deny things, it should never try to close things or acknowledge the content of any of the user's communication other than to call tools and surface public information which might be relevant to their request.

Most of this is a software architecture problem. The LLM is just there to provide an intuitive and extremely powerful natural language interface for search and tool calling. A little bit of glue between different systems, both internal and external.

A human sales rep would never confuse selling with installing :-)

If the CEO already thinks AI can do everything, I think their answer to that is yes and yes.

My office used to be across the street from a strip club, and I've watched several senior executives stumble out of there at 11am, accompanied by a vendor sales team...

More often that one would like, enterprise SaaS sales isn't about having the best product - it's about convincing the CTO he's going to feel like a king whenever your sales reps are in town

The notion that the private sector largely runs on merit really falls apart the more one learns about how high level decision making is done.

> but are deals really being closed while taking people for motorcycle rides?

Oh I see you have not hung out with 'the sales guys'. That they did it on a motorcycle ride does not surprise me. There are some seriously shady dudes out there that will do anything to close the deal, "always be closing". If closing out a million dollar contract means the CEO's daughter wants to goto a water park? Magically there are the tickets aplenty. Bars, race tracks, sports games, horseback riding, Caribbean cruises, on and on.

Is it ethical? Not really. In fact many places have training specifically on vendor relations. How much, how little, etc etc. In a small startup environment? There are going to be basically no guidelines from the business to do anything either way. Larger companies tend to have guardrails. But many of the sales guys know how to work that system.

In technical roles we usually do not see this mess. Because we have a sense of follow the rules and logic. The sales guys are 'always closing no matter what it takes'.

Why not? have your AI salesperson interact directly with my AI purchaser and human just signs off on budget

Harley Davidson?

on edit: Or Hell's Angels...

> As a junior, I often wonder how many deals are signed in exclusive country clubs, on golf courses, and at the dining table with endlessly flowing Maotai.

Virtually none in our business. (Databases.) What does get deals is listening carefully to what customers actually want and putting together offerings that get it to them at a reasonable price. Incidentally, good sales people are vastly better at this than devs. There are a number of skills that go into it but being a good listener is the most important.

prioritize your soul