Ask HN: My CEO wants to go hard on AI. What do I do?

110 points by throwaway778 ↗ HN
I'm the lead software engineer at a company building a B2B hardware/software product in the US. Great team, great technology, great PMF and good progress on revenue targets. There are lots of opportunities for how to develop the product further. It's been an extremely hard scale-up but we are finally starting to see it pay off.

I'm struggling with the CEO being increasingly focussed on investing heavily in AI. I'm not opposed to using this tech at all – it's amazing, and we incorporate a variety of different ML models across our stack where they are useful. But this strategy has evolved to the point where we are limiting resource on key teams aligned with core business to invest in an AI team.

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.

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. 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.

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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 ;)

This is great advice.

> I've seen folks wanting big changes and we sit down and draw things up and surprisingly it looks like the old roadmap.

I've found myself doing this also. It also helps to reason through new nuances found on the same evidence, because we're more wise looking at the same data in the future, or in this case, in the present (looking from the past).

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."

That's a good point. Lots of software companies are trying to become AI companies, not because they believe they are truly AI, but because CIOs are willing to invest in AI, so everything must become something that can fit in that budget.

This will crash in 1-2 years as CIOs realize most of this is useless, because at that point all software will be "AI Software" according to the marketing department, and we'll reset to CIOs making decisions on some other metric, such as a guy they met at a conference.

Just put some of your normal features behind a button with a sparkles emoji on it. No one will know.
But then the customers wont press those buttons anymore.
Shit you're right. Back to the drawing board.
Put sparkles on the close account button!
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.

“Made in America” == “Assembled in America out of offshore parts”, only with AI?

(Also, huh - I wonder if that’s actually directly doable; “assembled by AI out of programmed outputs”?)

> AI efficiency initiative

Don't forget to name it after a dog, too.

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/

This approach looks to me like a classic mistake of assuming all your potential paying users both are and want to be (these are different things!) power users. Similarly it might be suffering from the problem of living on the cutting edge and assuming everyone else is too.

I like the post and what it goes over. I agree with huge swaths of it, especially the misuse of ai tools right now. I don't agree that anyone doing it that way (like the gmail team called out over and over here) is either stupid or naive. I don't agree every consumer tool should become an agent building playground. I don't agree building said playgrounds are easy (I think it's much much harder to design a good agent building version of a product than a good product). I don't agree consumers want everything they use to work this way. I also think it ignores the very real problem of ai bullshitting and the handcuffs that puts on people using it for mission critical things like paying the mortgage.

Ironically I think this post falls into its own trap of not thinking about the next step. Yeah a really good email agent product as demod sounds great in a world where nothing works this way yet. However, a world where every product I use has to be re-engineered from scratch, with various unknown and non-customizable (and enshittifying) LLMs under it, with various training and fine tuning, unknown access to data, and no interop is the wood-frame horseless carriage the author is mocking. That would be a terrible situation worse than the current one.

Rethinking for a world of ai agents, it would be better if products empowered consumer agents instead of tried to supplant them. In THAT world products stay simple and just expose a bunch of tools and patterns that each consumer's custom agents can effectively use. Making that work well for your own product is actually viable AND helpful AND doesn't force your users to change their behavior if they don't want to. Anything I, the consumer, do to handle or prompt my own agent pays off across my entire ecosystem and investment can be focused on the right things by the right people (ie gmail should make email tools not agent tools).

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 imagine there are a lot of stories like that from the "everything needs to be a mobile app" era.

So many companies invested vast engineering resources in building out iOS/Android apps only to later find that their users only interact with their tool once every few weeks, which wasn't often enough for them to earn a place in that relatively tiny list of a few dozen apps that any one individual actually uses.

For many users with cheaper phones asking them to install your app is asking them to pick which of their photos they're going to delete to make space for it!

In our case, it turns out people preferred using spreadsheets and word processors on a laptop instead of a tablet.

Seemed kinda obvious at the time; but that probably explains why the leadership was forced out.

I remember when the internet got popular (I'm old) and Windows 98 put hyperlinks in the OS and made a lot of stuff single click instead of double click and BOOM! "Internet ready!"
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.

The ceo likely has more voting shares alone. The issue for a cashflow negative business is attracting new money.
It is exceedingly rare that voting shares play a role in any of these decisions. When you need cash to pay salaries, the decision lies in the hand of the stakeholder with the cash, not the shares.
Like I said, if the business is cashflow negative the issue is attracting new money.

I think you’re going a little far with absolutes on your reply but it’s not really relevant anyway.

At a smart business, you work for your customers. If you're at a company that works for your investors, you're going to have this problem over and over again. In fact, you might as well give up on the idea of planning and decision making based on what would be best for the product and your customers.
I agree, having a boss sucks. Unfortunately raising investment from other people is not a way to escape it.

Note that starting a business with your own capital is not a way to escape it either, since you still have to answer to customers.

Difference is that customers are not (in general) asking to bolt AI onto everything, but investors are.
> At a smart business, you work for your customers.

Well, then you're bound to the amount of money customers can give you.

It's usually less than a VC partner with a god complex can give you.

> Well, then you're bound to the amount of money customers can give you.

You’re _always_ bound by what the customer is willing to pay.

Speaking more expansively, it’s just a proxy for whether the market will bear your prices/wants your product, and whether you are in the right place and/or positioning your product correctly.

VCs just add a temporary runway so you don’t have to be as concerned about that.

The market can be twisted to bear more through VCs. Uber's a great example.
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.

I came here to write this exact response.

Folks work in mission driven organizations. In organizations that are optimizing for dollars you see quality fall by the wayside.

Mission driven organizations that understand the levers of capital are the most enjoyable workplaces of my career.

You want a CEO who is customer obsessed, not a CEO who is maximizing for dollars in the bank at all costs.

It has to be mission first for a startup to be great, really for any critical endeavor.

Every for profit organization is optimizing for dollars, the next round of funding or to be an acquisition target. “Customer obsession” only goes as far as getting enough customers to be an attractive acquisition or another exit.
This might be a frame of reference issue. There are quite some small-medium businesses with a founder who is able to have more concerns in scope than "maximize dollars - screw it".
Has that founder taken outside funding? If so, it doesn’t matter what their belief system is.
I understand what you mean, but over here bootstrapping is the norm. Also funding can be boring loans from the bank, family loans, or business loans based on trust in the skills of the business owner.

So it doesn't always have to be an: you owe me the money, so I own you.

Exactly. Tech has become a place where “funding” has become synonymous with “find a VC to fund you”. Most businesses don’t go that route, and plenty of tech ones don’t either.

Savings, bank loans, lines of credit, private loans between people, local angel investors, and so on are how most businesses bootstrap.

I co-own a technology business that has never taken outside money (well, we do have a credit card) and I’m not really interested in doing that. I think VCs are more trouble than they’re worth because they’re so obsessed with growth that little else matters to them, and we’ve seen where that gets us in terms of customer relationships and product quality. And they always want just enough control to eventually oust executives they don’t agree with.

We’ve built our business up the old fashioned way: from a personal capital contribution from each co-founder and modeling pricing based on what the business needs. Clients who see value in that approach from their critical technology vendors are not impossible to find at all.

Without the runway of functionally blank checks, you do have to continually monitor your business model though.

Can you name one tech company of note that hasn’t gone that route? BaseCamp and who else?
Microsoft is listed often as example. Dell as well. Apple startet without VCs, but added one a bit later.
Microsoft and Apple were founded in the late 70s not exactly applicable in 2025 with a completely different landscape.
GitHub, MailChimp, stack overflow, craigslist, Zoho, pluralsight. Just ask an ai.

Or do you want to shift goal posts again?

And it's totally applicable right now given the recent collapse of VC funding.

Your qualifying statement is found some heavy lifting.

First 'tech company' is a very narrow band. There are lots of companies that were founded to leverage technology, but which do not consider themselves 'tech' companies. We're, for example a services business, the service we provide happens to use tech we developed.

Second "of note" is very subjective. Do you mean billions of users? Global brand name? Thousands of workers? Because those are very high capital outcomes achieved either via long time (IBM?) or massive capital injection (which leads to very financial motivations.)

Of course there are zillions of my smaller 'less notable' businesses that exist all around you and me. You've never heard of the company I work for, but we're well known in our domain in our market. We've never taken outside investment, and we're free to make a lot of 'discretionary spending' that often serves a purpose other than increasing dividends.

For example we pay low-end workers (non techies) substantially more than market rate (aka minimum wage) because we belive in 'living wage' principles. That directly reduces profits, which we can do because the owners care about many things, and money is just one of them.

Of course the business has to be a business. Of course it has to make money. But money is like blood. You need it to live, but you don't live to make blood.

Maybe it’s a PE backed company
> I've seen teams go for AI, do it well, and succeed.

Succeed based on what criteria? I struggle to think of a single product with "AI" that I'd call successful (excluding the already existing and established niches of recommendation algorithms and computer vision which have been rebranded AI and maybe are what you're referring to).

I'd guess "succeed" here == "VC gave them money".
You wouldn’t call ChatGPT a successful product?
It's not a "product that went for AI", the product itself is AI.
The difference becomes blurrier every day
"I've seen teams go for AI, do it well, and succeed"

Can you give any hints as far as industry or product?

To sum up what you said, some startups succeeded creating products and others did not, just like before LLMs. The majority of the failed ones are led by clueless CEOs trying to join the hype
There are too many stories out there of highly successful people who got that way by going 'all in' on some rising technology.

This causes too many company executives to think 'if we go all in on [latest trend] then the same thing will happen to us'. Very little thought is given to whether the latest thing is a good fit for what you are building.

When it is a good fit, things can really work to your advantage. When it is not, it can just be a monkey on your back.

> 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.

Is it really scamming VCs, if they're the loudest cheerleaders for AI?
I mean yeah but in a way it's kinda like a legalised pyramid scheme
And we wonder why the tech industry has lost the trust of the public.

Where could it have gone?

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.