Dreams and Delivery
Real stories from tech pros who deliver at work and build their dreams alongside it. We cover the tech landscape in an age of AI with layoffs and opportunities that come from change. Techy creatives, this one’s for you!
Dreams and Delivery
Jack Smith: IT Horror Stories - Building Skills that Outlast AI
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This is a conversation about what happens when AI screens resumes before a human ever sees them, why “AI integration specialist” means something different to everyone who says it, and the case for staying a generalist in a market that keeps chasing the next niche.
We also get into the quiet cost of the specialist bet, how fast a hot skill set can turn cold, and why the people who keep their base skills sharp are the ones still standing when the trend moves on.
Jack Smith started his career installing Windows 95 as a HelpDesk Tech and has spent the years since moving data centers, opening data centers, and learning over and over that the skills worth keeping aren’t the ones tied to a single tool or title.
Now, as AI reshapes hiring on both sides of the table, he’s watching the same mistake repeat itself: companies rolling three jobs into one impossible profile, and candidates rewriting themselves into keyword matches for roles they’ve never actually done.
Bonus: what 25 years of hard-won IT stories taught Jack about learning from failure instead of hiding it — the same instinct that led him to launch his own podcast.
About Jack Smith
Jack Smith is an Infrastructure Project Manager and the host of IT Horror Stories with Jack Smith, a podcast exploring the human side of technology. He spent more than two decades building a career across cybersecurity, data centers, networking, and digital transformation, learning that resilience comes from what you take from failure, not from avoiding it. Outside of infrastructure work, he’s been part of the demo scene — real-time digital computer art on old and new hardware — since 1991.
Connect with Jack: ithorrorstories.eu | LinkedIn | Spotify | Apple | YouTube
About your host
Christine Kahn is a Staff Technical Program Manager with 12+ years leading AI platforms and program delivery at Intuit, OpenTable, 20th Century Fox, and Realtor.com; and a musician and soundbath practitioner outside of it.
Connect with Christine: bio.site/dreamsanddelivery | LinkedIn
© 2026 Dreams and Delivery LLC. All rights reserved.
Welcome to Dreams and Delivery, a podcast for tech professionals, real stories from people who deliver at work and dream beyond it. I'm your host, Christine Kahn. By day, I'm a staff technical program manager in big tech. By night, I'm a musician and a soundbath meditation practitioner. This is a conversation about what the hiring landscape actually looks like right now. Which skills hold when titles get rebranded as AI reshapes work, and how someone with deep infrastructure knowledge figures out which new doors are genuinely worth walking through. Jack Smith is an infrastructure project manager who began his career on an IT help desk and spent more than two decades growing into leadership roles across cybersecurity, data centers, networking, and digital transformation. Throughout that journey, he learned that success isn't about avoiding failure. It's about learning from it and continuing to move forward. Today, he combines those lessons as the host of IT Horror Stories with Jack Smith, where he explores the human side of technology and the stories behind the systems that keep our world running. Jack, it's so nice to see you. Welcome to the show.
SPEAKER_00Thanks for having me on. I have gray hair, I have a gray beard. My first job was installing Windows 95. So that's uh that puts the start of my career in the late 90s. And I have done technical things for about uh five, six, seven years, and then moved on to more organizational things. So that I did some boring things as planning and change management and release management for few companies, and then moved into what is called IT infrastructure, and that means, in theory and in reality, I spent the last 10-15 years moving data centers, opening data centers, putting new cables into warehouses, moving companies, and make sure that they had all their network in place, their power in place, their external network connections, their internet, and then with all the new advanced stuff technology today, is it how do we keep on doing it and how do we translate this into what the market needs today and what it does not need today?
SPEAKER_01Would you say that along the way you've developed certain skills that transfer from different jobs to different roles?
SPEAKER_00Absolutely. So you start off as technical, everything is planned for you, you don't need to worry about silly things such as a budget or a communication with a supplier. Well, with a customer, yes, with a supplier, you don't care. You just open the PC out of the box and you set it up. And when you go into different roles, you you kind of must have a base knowledge for some skill, but it lets you evolve it and grow it, and from there excel it and become very, very good at it. And over the years doesn't go in weeks or months, takes years because you also need to find out what doesn't work.
SPEAKER_01So true. Can you paint the picture of what the tech hiring landscape is like right now, especially with AI in the mix?
SPEAKER_00What I've noticed, well, it's more once you get past the hiring, it's okay. Currently, the hiring process is very AI-minded. So, what I see is that everybody is using AI to write their resumes. All the hiring companies are using AI to scan through the resumes, and in the end, I see very few correct profiles get hired. If I look on the job market, I see the same request for say somebody wants a senior Java developer. I'm just making things up.
SPEAKER_01Yeah.
SPEAKER_00I see those things come by again and again from the same company every three months, which means that the hire that they did was obviously not a success because they cannot be growing that fast that they knew that they need three to four new developers every month. So the things aren't really working out. And I've noticed that this initial non-human hands-attached screening is luckily going away, and that the right people are getting the right opportunities and the right shots at a good job again.
SPEAKER_01What would you say people are doing wrong from the hiring standpoint with you know using the AI tools? What do you think is the issue there? Is it just the way they're describing things or keywords?
SPEAKER_00Keywords mostly. I've had a thing myself where I was not myself but helping someone finding a job in the IT infrastructure world. And the resume that was sent out said, okay, this person has 10 years of data center experience, has five years of cloud experience, so with cloud systems left and right. And the feedback that got was, by the way, completely AI-written email. You could just tell from the way it was it was formed, was well, yes, you have a very interesting resume and we will keep it on file. However, we do notice that you have five years of cloud experience, but we were looking for public cloud experience. And then because the search term was public cloud instead of cloud, they completely missed out completely human hands off this perfectly fine technical person that would have had a great career in this company.
SPEAKER_01Yeah, it's maybe a little too strict in the definitions or just the wrong definitions.
SPEAKER_00Yeah, it isn't it is an ant-and story. And say you want this many years of of experience, it's not checked. So you need experience with AI building, and they said, well, okay, sure, but nobody knows, oh, you need 10 years of 10 years of experience, impossible, that doesn't exist that long. Well, not in the big public market anyway, but still somebody types that in and it is not checked, it's not validated, and in the end, with all the well filters and search criteria, that's where things go wrong. Plus, that I do get the feeling that in order to save costs or to be more flexible or to use the terminology agile, many profiles are pushed into one. So you need to be and a scrum master and a project manager and uh be a top negotiator in everything and vendor management, which used to be three positions 18, 24 months ago, and it's now all rolled into one ball into profiles which don't really seem to exist.
SPEAKER_01Yeah, I'm seeing some new roles emerge to where they're just calling it a builder, and it's kind of a mix of an engineer and a TPM and a product manager in one. What are your thoughts on those types of roles?
SPEAKER_00Everybody is making stuff up on the go. It it is if you're like, okay, give me an elevator pitch in one sentence, what does an AI builder need to do? If you ask 10 different persons, 10 different people at a convention, you you will get 15 answers. Yes, they have to build AI. Well, yes, that's in the name, but what does an AI builder do? Nobody can tell you because they don't know. They're making it up on the go.
SPEAKER_01We talked about the hirers, but for people who are looking to get jobs, knowing that these AI systems exist in screening, what can they do to navigate that?
SPEAKER_00That's that's a that's a million-dollar question. I've seen some hiring agencies try to do say, hey, we have this uh job opportunity. Can you customize your resume, your CV, so that it includes all the proper keywords so that you will get selected by the top of the pile? It is a very natural thing to do and almost an automatic reflex because you want to get to at least a foot in the door with a single interview. But you're you're setting yourself up to fail because you are heading towards a mismatch. You you claim that you are a specialist in things that you cannot do while you are effectively hiding the skills that you do have and might be useful. So for myself, when I have to send out my resume to a potential customer for uh a project or for um helping out left and right, I I refuse to do it anymore. I have updated my CV so many times, I have have gotten zero additional projects with that method. It just don't bother. You can always polish a tiny bit, but don't go and rewrite it with any AI tool yourself. Also, refuse that any agency rewrites your CV for you because that's not you that you are suggesting, and then both sides will be disappointed in the end.
SPEAKER_01I've been testing the Claude resume rewriter to tailor things just to see how it works. And it really needs a lot of human in the loop. I am always going back and editing it because they will pull information that's not accurate from the job that is being applied to. And I'm like, wait a minute, no, like that would be a big problem if somebody thought that I did a certain language and that's not what my focus has been. No, so it's kind of scary.
SPEAKER_00I give you a good example because in in the in the early 2000s, I worked in logistics and shipping companies that had still and they still have today, mainframes for all the big bolt order processing and all the package tracking. And I listed it on my resumes as okay. I have worked with these systems, I know they exist. And one of those AI systems just made me a specialist with 20 years of experience in the mainframe field.
SPEAKER_01Oh my gosh.
SPEAKER_00And if you just send that out blindly, then you you can say, Oh yeah, we saw that uh you have uh IBM mainframe specialty for 20 years. You are the person that we're looking for, and you have to tell the hiring manager, like, I'm sorry, I haven't touched those things in 20 years. But thanks to hallucinating AI, well, there that's where we are. And we have wasted everybody's time, and this is a complete mismatch.
SPEAKER_01Yeah. You know, some of the the roles I've been seeing are AI transformation lead or say, you know, just a new it almost seems like the same thing as a program manager, but it's just rebranded to what is savvy now, AI program manager. So what I would recommend to people is to look at the skills that you have and how they translate to those roles. But it's a little bit challenging sometimes to even know what to search for when you're looking to apply to things.
SPEAKER_00Yeah, you kind of have to guesstimate what they're actually looking for. Because an AI integration manager, what's the actual job description? Do you need to set up an AI system? Do you have to move to an AI system? Do you have to get people acquainted and used to working with AI systems? Those are three different jobs that fall under the same umbrella. Like, what do you mean? They don't know.
SPEAKER_01Yeah. Do you think that we're gonna see more specialist roles or more generalist roles nowadays?
SPEAKER_00It's it's common evolution that a generalist always survives. A specialist can be very good for a short period until the specialty dries up.
SPEAKER_01So it's more temporary.
SPEAKER_00It is temporary because everybody will now need to have AI integration specialists. Well, well, once the AI is integrated, what are you gonna do? Because you might be the best AI integration specialist in the world. Well, there might be 5,000 of them, but they're only looking for 250. Now what? Of course, it's it's good to have those additional skills and use that skill set, but keep a generalist skill set as well. So keep on doing your planning, your budget, your communication. Don't throw that out for this one specific niche market unless you are ridiculously good at it and you can make enough money in the sector that you can retire in five years. Then absolutely go for it.
SPEAKER_01Yeah, I think back to when agile and scrum became popular. It was all about agile transformation. And before that, it was lean transformation. And so it's really the underlying skill set to be able to drive change.
SPEAKER_00People with lean six sigma belts, are you doing today? Please tell me how is AI working for you?
SPEAKER_01One thing I was wondering is is it gonna matter that I don't have a PMI, which is Project Management Institute certification? It never stopped me from moving up in my career because I had the experience and the ability to learn on the go.
SPEAKER_00The only place where I found those things interesting was twofold. One of them is if you are hiring and you have the choice between two candidates, exactly the same skill set, soft skills, hard skills, they are they're asking the same money, they have the same experience, and then one has a cert and one doesn't, there it there you can use it as an additional differentiator. You will also see, and then this is more technical, if you want to be, say, a partner for a tech company, like say Microsoft, say Oracle. If you want to have a certain level that you can be a silver, gold, platinum partner, you will need an X amount of certified people in your team on your payroll. So there you need to fill that buffer so that they can say, hey, this gold partner has this has this skill set available and we've validated it. In those two spots, yes, I can absolutely see it. Otherwise, it is limited unless, again, you go really, really, really specialized. If you have all the higher level Cisco technical certificates, then you can skip the interview because if you can pass those, you know what you're doing.
SPEAKER_01Yeah, I think it's it's just like any other return on investment situation where you have to see, is it worth my expense for this certification or this degree, say some master's or PhD compared to what the incremental improvement in the salary would be. What tips would you give people who are trying to navigate this crazy environment in hiring right now?
SPEAKER_00Do not go and change yourself or present yourself as to something that you are not. I know times can be tough. I know that the hiring market is not fantastic these days, certainly not in the IT field. I see this around me. I know that my personal projects have gone down from 200% to a busy to 100% busy. So you do see it in the market, but don't go and sell yourself as something that you are not, although the urge and the temptation is absolutely there. Of course, you can you can aim high. So like I have some knowledge of this, and I'm just gonna aim high and say that I'm a specialist, go for it. Because you because you don't know what the hiring company is saying by what's a specialist. Is this somebody that knows how the menu works, or is this somebody that can design this on the back of a napkin from scratch?
SPEAKER_01Yeah, good advice. And I think now more than ever, leveraging our networks and having that human connection is going to be the big differentiator in getting access to those roles because oftentimes things get listed internally, but not yet externally. And if you know somebody, then you can have a chance to apply sooner than it even becomes public.
SPEAKER_00That is one way to do if you can if you can do it. And I've had some experience in that. And yes, you can some well, you can cut out the middleman that it's not posted on any uh job hunting website or goes through a headhunter or is posted on LinkedIn. However, even when headhunters say I have exclusive access to this position and I'm the only one who had it, you have three, four other headhunters that contact you anyway within the next two days. So you will pass a certain first screening, but second and third is always there. It is not like, oh, I know a buddy, he'll be good. You can just hire him straight off the street. I don't see that happening all anymore.
SPEAKER_01Another tip I recently learned is if you're applying, you want to go directly to the hiring company's website so you can get into their data system as soon as possible. If you go through an agency or even LinkedIn through their EC hire, it's a little bit slower process to get where the data needs to be.
SPEAKER_00Yeah. Well, it it depends on how the data is treated, and you don't know this upfront. Entire um the LinkedIn system or an agency, they can throw it through an AI filter with their hunt for keywords, and then you don't know. But sadly, the same goes directly for the hiring company because they you don't know if they prioritize the website list or if they look at it secondly when the other things don't come up, because a bit of well, people are now applying via multiple ways if they see something that they really want to get or at least have a shot at. Talking to some headhunters where, say, 24 months ago you would they would post a job out in the field and two of their colleagues would send it to their cousin or their brother and they would get some uh job applications in plus three, four from the market. Today, if something is posted on, say, LinkedIn, they have 500 applications. It is extremely difficult to stand out. So if you have the luck that they first look at the internal ones to the website, sure, it might help. If it's ignored and you don't know this upfront, well, at least you've tried.
SPEAKER_01I saw something the other day where a company was skipping the resume review and asking people to create an AI agent as a challenge and submit that as their entry to get the job. It's very interesting, and I'm not sure how I feel about it yet.
SPEAKER_00You just go to a cloth and say, make me an AI agent. I mean, yeah, it's easy to do, but to expect it it proves absolutely nothing because something with AI, which is then scrutinized by AI, and in the end, nobody gets hired. That's exactly what I started with.
SPEAKER_01Yeah, it's the same problem in a different form, but you had to spin out a little more effort to do it this time around.
SPEAKER_00Yeah, okay. You need to buy some tokens.
SPEAKER_01Tell us about your podcast and how this became your project, and if you have any other fun projects going on you want to share about.
SPEAKER_00I have a few, and uh, sometimes I have too many. But no, uh the podcast started out because I'm doing this now for over 25 years in IT, everything with the PowerPlux. Okay, I want to share my knowledge and partly my misery, and how do how can I prevent other folks from having the same steep learning curve that I had? So my magnificent idea was that hey, I'll write the book one once I'm semi-retired, and then I'll just see how that goes. And then somebody who was smarter and younger than me said, Well, why don't you just start a podcast? I've already been streaming some stuff with old computers, uh, look at my background, for the the last five or ten years. So I had the experience, okay, sure, let's get this thing going. I have stories of my own from my network. People can come to me and uh tell them the story. So we're not focusing in the podcast on the blame game. We're focusing on the what can we learn from this? What can we do to prevent this in the future? And it can go from a technical decision to a business decision to a planning decision, and it is sharing well, partly misery to make it fun and tongue-in-cheek, but also to share the knowledge how we're doing this, and and we are now in our second season. We started this about um April, May of last year, and we're uh now publishing two to two to three episodes a month. We don't have a really fixed schedule, we don't want to stress, we want to go for quality over quantity, but I do feel that we're getting there.
SPEAKER_01Yeah, I love how relatable the topics are. I listened to a few, and you know, a lot of people who are in tech heads down, they get it. And being able to go from that frustration to okay, well, what do I learn from this is really important. So I'm glad that you're putting that content out there.
SPEAKER_00Yes, indeed. And um, otherwise, well, as as I said with old computers, I'm active in something called the demo scene since 1991, which is a very long time ago, where we do, say, digital computer art, that's how we sell it today, uh, on old computers and new computers. Say, imagine you have a cube running on a screen that is cool. If you make it shiny, that is cooler, and we try to do it real time, so it's like a non-interactive movie that is uh generated. There's an entire internet out there that will teach you, and I can make an entire podcast series, there are podcast series on the topic anyway. So I'm not gonna delve deeper into that. But if you look it up and have some fun with old and new computers, that is also part of things that I do, and they still have power plugs. I'm stuck with those.
SPEAKER_01Very cool. Where can people find you if they want to connect and potentially partner with you?
SPEAKER_00The podcast is it horrorstories.eu. EU because we are based in Europe, and if you type IT horror stories with Jack Smith into any favorite search engine, you will find the website. You can find the podcast on the usual platform, so that is uh Spotify, Apple, YouTube, Deezer, and everything that feeds from that. We have some social media as well. We focus on the more techy ones, so uh LinkedIn, Mastodon, and Blue Sky, although we also have almost call them legacy, but that's kind of what they are. Facebook and Instagram profiles for those that are not into the uh more alternative social medias.
SPEAKER_01Wonderful. Thank you so much, Jack.
SPEAKER_00Happy to be here, Christine. Thanks for having me.
SPEAKER_01To everyone listening, if this resonated, subscribe and share it with someone who needs it. I'm Christine Kahn, and this is Dreams and Delivery.