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Who Will AI 🤖 Really Replace in Tech?

Wed, 10 Sep 2025 14:48:00 GMT

the fear is real, but is it warranted?

I was looking at some data with a few colleagues on the makeup of SaaS companies built on AI (meaning they've woven AI into all their processes an built their company this way from th ground up) and SaaS companies not built on AI.

A couple take-aways:

The departments where AI replaces all/most people:

Marketing
Sales
Success/Support
Finance
HR
Executive leadership

We were musing that cutting way back on Finance and HR can't be sustainable due to legal liabilities that are bound to ensue. The thought is that these companies expect to be acquired fast and early. Though if you have so few people in your org, there are fewer people to manage/pay.

Also there is something to be said about that personal touch �� in customer-facing roles, especially revenue generating ones, so as revenue grows, those departments start slowing ticking up which, in-turn, cause operational departments to slowly grow.

Executive leadership is interesting... it's way too optimistic to think that AI could be the great equalizer in wealth, but it's a nice dream to have. Also, this is against my best interests since I'm in executive leadership ��.

Engineering was leaner at the AI-first companies, but not non-existent. This tracks with my take, which is that AI is not at the point where it can replace engineering and GenAI never will be. It can augment engineering and make them more efficient, but IMHO, GenAI will never be able to build secure, maintainable SaaS applications.
- Websites: yes.
- E-commerce Sites: maybe.
- Prototypes: sure, but only if you are OK that it will be mostly throw-away code.

My unpopular take (and you can quote me on this):

�� AI prototypes are today's vaporware ��

But here's the most interesting part

The one department that had no material difference in staff between AI-first and non-AI-first companies:
�� Product ��

This surprised me at first, but after some thought, it made complete sense:

♟ GenAI will never be strategic
�� GenAI can help brainstorm, but can't make decisions

‼️and perhaps most important‼️

��‍�� GenAI will never be able to invent new things.

And so if you are lucky enough to have found yourself in product management, congratulations! �� You have picked one of the most AI-proof careers**.

** This is IFF all companies value product management and not all do, but those that try to replace you with AI will undoubtedly fail and then we can all feel smug in their downfall.

Startups: When to Hire Your First Product Manager

Wed, 23 Apr 2025 20:01:06 GMT

We don't need no stinking product management!

The Birth of Software Product Managers

I started out my software career as a subject matter expert (technically a “Business Analyst”) at the turn of the century – 1999 to be specific, with Y2K looming over our heads. But I didn’t need to care about Y2K, right? I was an SME. Issues regarding 2-digit years and the new millennium were not our concern – that was engineering’s problem.

I was working at a startup that was about 8 years old when I got there. It wasn’t technically a dot-com. It was a fat client/server application. I don’t remember if it was PowerBuilder or Java Swing, but it was something of that ilk. When I was hired there was a push to re-platform all our products as web applications, but on our own hosted servers because this was well before AWS.

We built global trade compliance software (essentially software that helps you file the right paperwork with a country’s customs agency to properly import or export your goods into/out of a country - though there are a lot of complex rules depending on what you are importing or exporting, in addition to rules from other agencies like Food & Drug and Agriculture and Defense, but I’ll stop boring you here).

I was hired because the current SME was having a really hard time translating government regulatory requirements into something an engineer (with no domain expertise) could code off of. When I interviewed for the position, I happened to be an expert on US Customs import rules and regulations with no experience in software, BUT I had a technical degree.

The hiring manager was excited that I had taken programming languages in school. I told her that it was Pascal and Fortran, so I’m not sure how valuable that was. (Side note: this was before I learned to <ahem> embellish my qualifications to appear as qualified as possible, though this was also when tech companies were throwing money at people with marginal experience... Y ou have a degree in underwater basket weaving? YOU'RE HIRED! ⬅ This isn't really much of an exaggeration. I had a friend with an art history degree and she got hired at a tech company and had absolutely no idea what she was doing and they didn't seem to care.)

Anyway, the hiring manager said, “I don’t care. If you know how to program, you know how to be logical and if you can be logical, you have the skills to translate business into tech.”

And lo and behold, she was right…

When I started there was really no such thing as a software product manager...

. ..OK, well this isn't technically true. Intuit introduced the concept in the 80's basing it on the "Brand Man" concept created by Proctor & Gamble in the development of fast moving consumer goods (FMCG). Then in the 90's Microsoft introduced the "program manager". It wasn't until 2001 when 17 technologist drafted the Agile Manifesto that the role of software product manager really took off because this role was integral to a scrum team. (Yes I am old enough to remember the birth of Agile.) Prior to that when everyone was used to the "waterfall" method, BAs would basically throw giant specification documents over the wall at engineering, dust their hands off, and then hope for the best. This almost always resulted in craptastic products with missing functionality that didn't do what the BA expected, resulting in missed deadlines, long hours of rework, and sometimes (almost always) crying, shouting, and finger pointing and a rousing game of "not it" when customers had to be notified of said missed deadlines.

Not long after I started people figured out that I actually could translate Customs rules and regulations into something engineers could code off of (I could even spoon-feed them pseudocode). Then we became early adopters of Agile and thus the software product manager role was born and I was the first one (I mean... not like the first one ever , but the first one at that company).

Bridging the Gap Between Business & Technology

It took 8 years for that company to realize they needed someone to bridge the gap between business and technology. The product I was hired to work on was brand new with no customers and in terrible shape. It was virtually unusable. During my first week there I attended product training for the product I was taking over, and I had no idea what was going on within the application and I UNDERSTOOD the regulations and the processes - or at least I understood what the processes should have been. Even the instructor got confused and lost. Several times. There were many times during this training that I could tell she wanted to throw her hands up in the air and just say, "Fuck it!" and call the training done.

The company already had an established product to help with export regulations, but export regulations are infinitely less complex and easier for laypeople to understand than import regulations (my inherited product's wheelhouse).

<being rant> Contrary to what the current administration would have you believe, the tariff system is extremely complex and a lot of thought is put Into what tariff rates should be for EACH INDIVIDUAL THING imported Into the US based on what we produce, what we do not, and what we cannot. A blanket tariff by country is one of the most imbecilic things I have witnessed In my life. But I digress. </end rant>

Where was I? Oh yeah... so there is no doubt in my mind that, had I not been hired, that product would have failed. I know this sounds super braggy and I don’t mean that it had to be me specifically, but they needed someone different than the non-technical SME that I replaced. They needed a product manager. (Stay tuned for a follow-up post on my unpopular opinion that the most effective product managers need to have a technical background.)

Incidentally, that product still exists today, 25 years later. It was bought and sold several times over and (hopefully) re-platformed a few times, but it is still a viable product (this bit is intentionally super braggy).

Most Seed Stage Startups Don’t Have Product Managers

Fast forward 25+ years and most startups still don’t hire their first product manager until several years in. 2-3 years seems to be around average - either that, or around the time the company has hired between 1 and 2 dozen engineers.

In cases where the founders are engineers, generally one of the founders can effectively act as the product manager (though not all engineers are good at this, which seems to contradict my statement above that product managers should have a technical background, but it does not and you're just going to have to hold your horses until I have time to write that post before you flame me). Also, in cases where the product is something familiar or tangible (most B2C products), it’s easy to get by without product management for a good long while if the engineering team is small enough.

Regardless, even 30ish years after the inception of the software product manager role, product managers are almost never an early hire, UNLESS one of the founders is a product person – in those cases they realize that the skill is necessary, and that they don’t have the bandwidth to do that and their executive role.

You Don’t Know What You Don’t Know

Most (not all) startups are created by engineers with a great idea, but they often know nothing of ideal customer personas, market or market fit, product vision, etc. This is fine and perhaps even good. Too much structure and planning can squelch innovation and if they can manage to get an MVP out the door without outside investment, they won't have VCs breathing down their neck telling them what and what not to do (which can also squelch innovation, but in time having some guidance is a good thing).

Because product management tends to be an afterthought, startups often don’t start thinking about the skill until they start floundering. Maybe they can’t figure out who their ideal customer is. Maybe they know their ideal customer, but they aren’t gaining traction because they aren’t prioritizing the right features. Maybe they aren’t getting anything done because startups with no product oversight often like to run to the next bright shiny object only to be distracted by another bright shiny object (otherwise known as, “SQUIRREL!”).

I’ve been hired as the first product person in most organizations I’ve worked and the one thing that everyone has told me is, “I wish I would have hired you sooner.”

There is this sweet spot within a startup, usually sometime after MVP and sometime before the company starts floundering (at some point, without product oversight, the company will start floundering, even if otherwise successful), is where they should start looking for a product manager.

The first product person should be a combination of strategic and tactical. They should have several years of experience. Often companies will try to train an intern or use an engineer to fill that gap, but you need an experienced product manager. The product person needs to be someone who’s willing to roll up their sleeves and work alongside the engineers day-to-day, as well as talk with stakeholders and customers, while putting in place a process for their role. They cannot be someone who just builds roadmaps and defines OKRs and throws them over the wall to engineering. An engineer in this role may provide more technical guidance to help get features out the door, but this person also needs to be able to identify what features to build (or, more importantly, not to build) and when.

what can A Product SH3pherd do for you?

Hiring a product SH3PHERD in early stages can benefit startups by providing some structure without disrupting the engineering process. A product SH3PHERD can help build out product vision and strategy and ensure that these align with the company’s overall strategy. They can also help with product-market fit and provide go-to-market and launch plans and ensure that the product aligns with customer and stakeholder needs. All of this will help guide the roadmap and prioritize feature development. In essence, a product SH3PHERD will help build the foundation for the first product manager.

Some people will hire fractional CPOs for this role, but the term “CPO” is kind of a misnomer. Fractional CPOs should also be willing to help execute on the product strategies they’ve defined and ideally, they should be there to onboard and coach the first product manager.

A product SH3PHERD can help smooth the rough patches in a startup’s early stages without spending the money up front for a full-time product manager (product managers are expensive). Once the foundation has been set, the first product manager should be able to hit the ground running and execute.

Introducing: The startup SH3PHERD

Fri, 23 Feb 2024 01:35:11 GMT

Welcome! Come on IN!

Meet Tank and Rocket, the first two unofficial "employees" of SH3PHERD. They don't actually do any real work, but they do provide me with a good reason to actually get up from my desk during the day, walk around, stretch, and take a short mental break, which is important. I'm the type of person who can get so lost in work that I'll even put off getting up to pee until I absolutely can't stand it (which is a really bad habit, especially if you want to avoid wearing diapers in old age).

Tank and Rocket are Shiloh Shepherds. If you google "Shiloh Shepherd" Tank actually shows up as the first picture in an image search, and Rocket shows up in the top 10.

I won't bore you with the history of Shiloh Shepherds, but you can see that they are related to GSDs. Regardless, Tank's full name is Gen. Ulysses S Grant and Rocket's full name is Gen Don Carlos Buell, who are two of the Union generals who won the Battle of Shiloh . Yes I am a big dork.

Anyway, when I created my logo for my personal consulting business ( H3ATHER.tech ) I wanted to pay homage to Tank and Rocket, so I got the idea of incorporating a robo-shepherd in the logo.

And then w he n I decid ed to create my original blog, I needed to come up with a good name. Tying it to the Tank and Rocket theme didn't occur to me initially and I actually used ChatGPT at first and it came ujp with a bunch of craptastic suggestions.

The only passable suggestion was "The Product Whisperer" but I'm sure that was probably taken and it's also kind of trite.

But then it occurred to me that product management is a lot like herding cats. If you are unfamiliar with the origin of that term (or at least the origin of the term's mainstream popularity), it was from a Super Bowl XXXIV commercial in 2000 for EDS, which was an IT consulting company. This was back when tech companies were throwing money at everything and everyone and trying to outdo each other with the best Super Bowl ads. It was also the year I became a product manager for the first time

It was only after I considered naming my blog "The cat herder" that I realized that the perfect name was staring me right in the face, and so "The Product Shepherd" was born. But then I decided to expand my personal business to provide a variety of other services besides just product management and SH3PHERD turned out to be the perfect name.

Early startups founders don't need more executives. They need guides. They don't need people who just tell them what to do to get to where they want to be. They need people to guide them on their journey along the path to success and to protect them from taking the wrong path, or taking useless diversions that waste time, so they can get from 0-1 in the most efficient and effective way possible.

Photo: Warner Bros.