Work with them on a product roadmap?

I've seen folks wanting big changes and we sit down and draw things up and surprisingly it looks like the old roadmap. Everyone is happy and I don't say anything about the similarities, and most importantly we're on the same page ;)

Sometimes when leadership asks for big changes, even when they say big changes, you might find if you get into the details it's not THAT big a change.

In the meantime don't let your mind run too wild assuming and worrying about what they might be asking for. I do that too, it's a developer thing I think, we start considering possibilities or even misused terminology and we get into a loop ;)

Tell him not to lead by news headlines. Try to explain what AI can't do. You could also be unscrupulous and make a lot of promises to milk this AI thing until the wheels fall off.

Relevant anecdote from Bill Gurley's talk: https://youtu.be/7PkWc-IDTHk?si=p8AUBHqXa76HuA6A&t=3228

"If the the average CIO is committing 10 or 15% of their budget to AI. If you're not in that you're getting shrunk."

Just put some of your normal features behind a button with a sparkles emoji on it. No one will know.

Bear in mind there is not always a strong relation between "what will improve the product", "what will attract customers", and "what will attract funding". A big part of the CEO job is to manage all of those at once.

As the engineer you need to support all three, while being the voice of realism (internally). But don't get confused when they conflict -- they always conflict to some degree.

Keep in mind that your company is the product. And the customers are Wall Street.

Your product is not really the product. So the only thing that really matters is how your company is perceived to those who could potentially buy it and give your C-suite an exit.

If you trust the CEO's leadership, work hard. The CEO has to worry about runway, not engineers.

If not, I'd say make a data-backed case for another course of action, or find another job.

Most CEOs I've worked with would be open to hearing a well-reasoned argument for another course of action.

Also presenting a good case can be a nice career move even if it's not adopted.

Draw up the product roadmap such that you can claim maximum AI-ness while including as little of it as possible in the actual product. Sounds like the CEO doesn't have any technical objections to not using AI, he just wants the ability to raise on AI branding.

Include as much non-AI work as you can in the AI teams' projects, pitch an "AI efficiency initiative" that minimizes new spend on AI with the justification of other teams picking up the slack, talk up whatever ML you're already doing, etc.

It seems like it's worth taking some time to steel-man the AI argument, even if your CEO hasn't made it very well.

E.g. If you don't work on AI now, and AI models keep improving, how likely is it that a competitor who integrates AI well will eat your lunch? If it's >50%, it seems worth it to shift some focus to AI regardless of the series C round.

This post from a few days ago has some great tips on how to integrate AI _well_: https://koomen.dev/essays/horseless-carriages/

Sounds like you are VC back. It is likely your VCs pressuring the CEO.

Your CEO is correct that ~80% of VC funding is currently focused on AI. So you have only 2 options basically. You either don't raise VC funding (which means hitting break even, rule of 40% performance). Or, you go all in on AI

If it's not an AI story for your business you need exceptional metrics. Like growing from 8M to 24M in a year for a C round.

Its normal. Too see it look at the financials. Don't look at the tech alone. Otherwise analysis is incomplete.

"useful, in-demand product features" have to generate revenue greater than cost. If its too low or execs think there are better ways to grow the firm then these decision happen all the time.

Trends come and go: What's important is that your CEO isn't underinvesting in the product.

I once was in a company during the "everyone is going to replace their laptops with tablets next year era." The CEO pushed heavily for mobile, and underinvested in the actual product.

A year later, all of our customers were still using their laptops. We were sold to a private equity firm, the CEO was pushed out, and (almost) everyone who worked on the failed mobile product was out of a job.

In your case, I'd try to decide if your CEO is just following a fad. If so, next year they will follow a different fad. Are you critical to your business? If so, you'll be critical to your business with or without AI. If not, figure out how to make yourself critical to your business without being vulnerable to this year's fad...

(...And perhaps ask ChatGPT for advice. If you can't beat it, join it.)

I would keep a more open mind and think about how you can contribute to the CEOs vision. As a lead dev, how can you incorporate AI into you and your team’s workflow? If you don’t agree with a tech CEO pushing for the latest tech adoption I would do some soul searching.

Unless you own the business, you work for your investors.

If investors only want AI, then you will either be forced to do that (whatever it means), do something else but make it look to them like AI, convince them they're wrong, or quit.

Things are a little more nuanced if your existing investors side with you but all new investors are AI-driven. Then you don't have to quit, but you do have to run the business without new outside capital. This may or may not be possible. If not, you still have to quit.

Who will be responsible for figuring out what AI features to build? I think it is reasonable to look into it, seriously, with the point of view of "can we disrupt ourselves before being disrupted." This doesn't mean putting a significant engineering team behind this, but, to put a significant effort in figuring out what is it you could build, and what an ROI on that would be.

You've two outcomes from this, either you do find a disruptive AI angle and move a sufficiently-large part of your team to it, or you don't, but figure out a minimal effort that would satisfy the "investor positioning angle". The third option, to do nothing or aggressively push back against AI and the CEO's desire, would potentially yield to no Series C or a down-round, which is something that you, your CEO, and your customers would not like.

I believe real value lies in solving customer problems - not just investor problems. This technology has significant upside when applied thoughtfully. That said, without proper validation, prematurely sidelining proven solutions to chase AI initiatives—especially without clear problem definitions - can be risky. It sets the stage for a bubble that may not withstand tougher times.

imho, I would like to think tough times are ahead of us - that in my mind, neutralizes my 'tech optimism'.

add AI to the products and features you want to ship, don't add AI to the ones that don't.

You want to start with at least an AI Roadmap that outlines whatever you want to do, and sprinkle in some AI love.

Without knowing more it’s hard to come up with specifics. There are different ways to play the AI game, from framework/architecture, model, data, fine tuning, to simple integration. You can do as simple as writing a mcp server to interface with your product and call it AI enabled.

From what I've seen, anyone giving you definitive answers is blowing smoke. I've seen teams go for AI, do it well, and succeed. I've also seen teams go for AI, f it up, and all get fired as the company shuts down.

The question is whether the key value of your product can benefit from the strengths of AI? If not, don't go there. If so, you then need to determine if your team can actually deliver an AI-driven vision that enhances the existing value prop. Again, if not, don't go there. If so, do it.

But from your description, your CEO is not asking those questions - they are asking, "How do we get more funding?" Which tells me that your CEO doesn't give a crap about building a product, they are just trying to make money and get some nice bullet points on their resume about the size of a company they led.

That puts you in the position of choosing whether you want to go on a VC-driven startup ride just to have the experience, or whether you want a product-driven role. People have their reasons for both directions, but if you want a product-driven role, you are out of alignment with your CEO and probably shouldn't work for them.

> The argument seems to be that they've realized the only way to achieve the next round of funding is to be "AI-first".

This is the argument for virtually every company going AI-first: it's just a way to scam VCs.

It seems crazy but it really works.

This is normal. It doesn't even have anything to do with AI.

The problem here is that your company is on the "get the next round of funding" train instead of on the "get revenue from customers" train. It's a bigger problem then irrational love of AI. You will consistently sacrifice the product and your customers in favor of whatever people think will get you the next round of funding. If you manage to solve your current funding crisis by convincing some investor that you have an AI plan, don't worry, you'll have another crisis in a few months.

Talk to your product owner and get the scoop. Maybe they're cooking up some new features that could really benefit from AI? Keep in mind there's always a buzzword du jour game being played to maximize VC investment. Help your company play that game and help them drive toward answering the questions you've asked. It's win-win from your perspective.

Right now, there are too many shovels, but not enough miners. That is to say, very few concrete use cases, but a lot of tool vendors.

Most AI "deployments" I have seen, are glorified knowledge search engines, or query engines. There are some content/code assistants as well. It is also the least intrusive way to be "AI - First". There is too much noise, too little value , but yet a significant pressure to be an "AI company". Most startups are feeling this (including the one I work at).

Unfortunately, VCs are always blinded by the next cool thing to invest in. So I think of it as a marketing feature that you have to build, rather than any real roadmap thing.

I had to think of the Dilbert comic strip where the pointy haired boss wants an SQL database and asks Dilbert what colour it should have.

Turns out someone already made a version with AI as the desirable technology du jour.

https://www.reddit.com/r/ProgrammerHumor/comments/1dckq74/so...

> There is no product roadmap for what this looks like

Think about it like a research project. The company or its culture may not be prepared for that, but that's what it is.

>> The argument seems to be that they've realized the only way to achieve the next round of funding is to be "AI-first".

Sounds like the CEO is more interested in selling the company than building the product. IMHO that's a bad sign. It's also notable that you're aware of AI and use it to some extent. That means you have understanding of what it can and can't do. So why then is the CEO telling you how to do your job?

> The argument seems to be that they've realized the only way to achieve the next round of funding is to be "AI-first".

You say there is PMF but this statement contradicts that. It seems that your customers are the investors and you need to sell to them in the next round.

I don't know what industry your company is in, but godspeed to your CEO on tanking your company with AI bullshit so that this stupid f**ing bubble pops and everyone can go back to thinking carefully using their brain instead of working on better serving Roko's Basilisk.

Couldn't be more excited for this kind of short-sighted, AI-instead-of-people thinking to become shameful. How many people need to aim the gun at their foot and pull the trigger before they're not bragging as they do it?

Call your existing ML models across the stack "AI," and wow him by reporting that you already are "AI"-first!

It seems that another round is necessary, and VCs want AI. You and the CEO are competent and transparent. This is the premises.

You just need to have the conversation with the CEO, but in the right order.

Come to him/her with objective data, but without your conclusions or concerns, just your observations about where this is headed and if he sees at what rate this AI focus is eating ressources. Ask the CEO what it means for the company. Let him/her do the talking.

From this point, the CEO have the data and you have the company policy. Know you can talk on equal grounds on the matter with him or her. Good luck.

This is where you need multiple levels of management so that you can create a different reality for the investors than for the engineers and then just chalk it up to “communication difficulties”.

The CEO needs to tell the investors that the company is all-in on AI. At the same time, the CEO needs to tell the engineers to use AI judiciously to support real customer needs, but not go hog-wild with it where it doesn’t make sense. This sort of situation, where you need to tell one group one set of facts to get them to act but another group a different set of facts, is fairly common in business (and politics).

The way big corporations handle this is to have many layers of management and a very diffuse set of responsibilities so that nobody is outright “lying”, they’re just interpreting what they’ve been told in a way that makes sense relative to their job responsibilities. The way startups handle it is to lie and hope that by the time they get caught, their results speak for themselves.

Your question needs reframing.

As it stands you’re stuck. If there’s no product roadmap showing how ai will help your product, being “ai first” Is meaningless bullshit.

But maybe if you reframe your question you’ll get a different answer. What does your company do? (You left out all the relevant information that might lead to a positive answer so you’re not even making room for it to be possible. If this is going to work out, you need to make room for the possibility, so start there. “What would it take for this to work? And what can I do to help”)

As a technical person you might be best suited to explore how AI could make your product better. A less technical person can dream things up but without knowing what is technically possible it might not be useful.

The absolutely essential next step in the conversation with your CEO is how do you envision AI being useful for our product. you might need to assist in this ideation (if not you, the most senior technical person at the company, even if you’re not most senior sometimes fresh eyes see something key)

Imagine you make a smart thermostat like a product built around the recent post about the bloke who reverse engineered his landlord’s thermostat to enable smart features and mobile control.

Is there room in that scheme for AI? Absolutely. If he rebuilt his project to be AI first he’d probably build it around voice control or integration so it can predict the user’s needs. He might grant the user the ability to ask conversationally for added features (I’ll be away for 3 weeks let’s turn the heat down and save some money. Turn it back on when you get an alert that my phone is 2 subway stops away.) Or he could build it around silently predicting what the user needs. But honestly it might not be worth recreating that project to be ai first. If it works and does the 5 things he wants what more is there to do? Saying “this is not a place that benefits from AI” is perfectly reasonable.

One place I’ve found AI to be useful is when interacting with the infinite variability of the real world. AI can look at data and transform it into the proper shape in a way that would take structured programming an infinite number of corner case loops.

Another area is offering conversational interface with large data sources or complex systems.

Another way is in rapidly building one-off integrations. (Staying on the smart thermostat page maybe there’s a new site where the system needs a new integration, you might use cursor to rapid prototype the integration)

In the same way there are places that are not a good fit for ai. Enumerate those too. Show up and run the good places for ai and bad places for ai against the list of features and technology you currently employ or to your known or imagined customer needs.

Ai is hugely powerful but just shoehorning it in everywhere is stupid and wrong. You should only use it if there’s a thing you can do better by using it. If you can’t see what that is you won’t ever be able to do it.

Here's what you should assess:

> Great team, great technology, great PMF and good progress on revenue targets.

Good progress on revenue targets from _your_ perspective sounds like not great growth, but communicated softly.

> The argument seems to be that they've realized the only way to achieve the next round of funding is to be "AI-first". There is no product roadmap for what this looks like, or what features might be involved, or why we'd want to do it from a product point of view. Instead the reason is that this is the only way to attract a big series C round.

This is not a thing a company does when they have good enough growth. Adequate revenue growth when you need a series C must be very good growth. Adequate growth when you'e profitable is a very different thing.

> Instead of working on useful, in-demand product features, it feels like we're spending a lot of time looking at a distant future that we'll struggle to reach if we take our eye off of the ball. Is this normal?

Yes, very normal. If I'm you, I'm wondering if there's really product/market fit. Useful, in demand product features almost don't matter. Building more does not make more money happen.

But also, the AI stuff is disruptive. In a way that the internet was. I think what you should probably judge most strongly here is if there is ANYONE with influence that has a take on how that looks for your company. That take probably includes "how this makes a lot of what we do irrelevant".

Absent that, I'd just write the company off. If you like the job great. If you don't like the work enough to be happy while the company atrophies, I think you're going to have a rough time.

The least harmful place to put AI might be in some kind of reporting feature that "provides deep insight into your data". :^)

There's a lot of open positions in the beachfront hospitality industry in various lovely spots around the world. Personally, if I wasn't the sole tech decision maker for my company, and some jerkoff told me we'd be pivoting to an AI-first approach, I'd have a bag full of shorts and Hawaiian shirts packed and be on a plane by midnight. I'd rather be making margaritas for entitled tourists and living in a goddamn hut than putting up with that shite.

Go hard - start by presenting <https://ai-ceo.org">AI-CEO. Find some middle-management AI's and some worker AI's, but be sure that the AI-CEO is front and center.

If he/she fires you, just say "OK" and walk away. Let him or her burn.

1. If you don't do it, someone else will.

2. It's more important that you describe a good story for your CEO to use, than actually implementing it.

3. Find/hire someone who can help you write the story. Just make sure that person has a weakness that ensures they can't completely replace you (see item 1).

4. Manage development speed, team expectations and priorities to the actual best of your abilities.

Will your company be around to do all the things that you feel are important if you first don't get the next funding round, which requires being AI-first?

That's really the only important question at this point.

I never understood this obsession with what the underlying technology is. Saying we need to be "AI-first" is like saying we need to be "Blockchain-first" or "Python-first." Who ultimately fucking cares what technology is being used to build a product? You could build it with acorns, and if the customer needs it, you should be able to make money.

AI is the future and the fear is we're going to get left behind

You're experiencing firsthand what's to be in the process of company enshittification.

What I can deduce is that the company (as PG would put it) probably is "default dead" if it needs so many investment rounds.

Since the first seed round, the company has been subject to investors' whim. Exit early, go very fast and see what sticks.

> The argument seems to be that they've realized the only way to achieve the next round of funding is to be "AI-first".

And what investors want is to jump on the wagon, regardless.

I don't despise AI; in fact, I love it. The idea of MCPs got me hooked up hard on it, now I'm the solutions guy looking for a problem.

The issue here is: irresponsible AI adoption (or any emergent technology for that matter, e.g., blockchain, VR, etc) will break companies.

I'm all in for AI, but implement it where it adds the most value and cascade with it to the next area it adds value until its implementation hits a diminishing returns ROI.

> I'm not well-informed enough to know if this is the correct approach to scaling. Instead of working on useful, in-demand product features, it feels like we're spending a lot of time looking at a distant future that we'll struggle to reach if we take our eye off of the ball.

Your internal compass is pointing at the right north star...

> Is this normal? Are other organizations going through the same struggle? For the first time in five years I feel completely out of my depth.

But unfortunately, this is becoming more of the norm, we can't help ourselves. This is what market meltdowns and market corrections look like months before they happen.