AI Unraveled Special Edition: 💰 Jobs Stacking with AI: From 80K to 390K by Special Guest Delaney William, Founder at Elevated Technologies
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Welcome to a special deep dive from AI Unraveled. Today we've got a really fascinating story. We're joined, well, we're discussing Delaney William, the founder of Elevated Technologies. He managed to increase his salary from $80,000 all the way up to $390,000. Wow, that's quite a jump. It really is. And he did it, you

using job stacking and AI. So our goal today is really to dig into how he pulled this off and maybe more importantly, how you, the listener, could think about these kinds of strategies. Absolutely. Delaney's journey, it really gives us a compelling look at navigating today's job market and leveraging technology that's, well, readily available to boost earning potential, gain more control, really. Yeah. Control seems key. So where was he starting from? He studied IT and marketing, right? And then spent about seven years in corporate health care.

Product management. Yeah, he called it a non-sexy role, which probably resonates with some folks. Product management, just quickly for listeners, is kind of the business side of tech. Planning, apps, strategy, not the actual coding bit. Got it. And he felt frustrated there. Lack of innovation. That's what he said. Felt stagnant. And, you know, that feeling often pushes people, makes them look

Elsewhere for growth. Makes sense. So he started looking into side hustles. Exactly. Online business stuff, service based businesses, even health coaching. He spent a few years figuring that world out. So he was already kind of entrepreneurial. Definitely seems like it. And that experience probably gave him a different perspective on his own skills. You know, how valuable they were outside that one corporate box. Right. And then came the aha moment, as he put it.

He was working hard trying to sell his coaching program, making a few thousand per client, which he said was tough. Yeah, selling coaching isn't always easy. And he realized, wait a minute, I'm making $80K as a product manager, but the market rate for someone with my experience is way higher, like 160Ks, maybe more. Ah, so the light bulb went off. Totally. Instead of grinding away selling coaching, he thought, what if I sell my product manager skills?

to multiple companies. OK, so that's the core idea, not just one employer. Right. Forget just one $80K job. What about two, maybe three roles, each paying, say, $150K, $160K? And doing it efficiently, working on his own terms. Exactly. Getting the 40 hours of work done faster, taking back control of his time. That was a big motivator. And it worked. What was the result? Pretty incredible. Within 11 months, his income hit $390,000. Whoa. Yeah.

He kept the original $80 K job, added $160 K1 and then another $150 to one. Three product management jobs. Three roles simultaneously. Yep. He thought about swapping out the $80 K1 for something higher, but decided against it to focus on starting his. Yeah. Since early 2024, they've helped about 30 people land and importantly, scale remote jobs.

teaching interview skills, work efficiency, the whole package. So he's basically productized his own success strategy. Kind of, yeah. Now, I know people listening might be thinking, OK, juggling three jobs, remote work, conflicting meetings. Sounds intense. Yeah, the logistics seem daunting. That's definitely a hurdle people see. Totally valid. And we are definitely going to get into the nitty gritty of how he managed that. But

But first, maybe we can just clarify exactly what we mean by job stacking. Just make sure everyone's on the same page. Good idea. So job stacking. You might also hear it called over-employment or being over-employed. Right. It's simply working multiple jobs at the same time. And usually we're talking about legitimate full-time type roles, you know, where each company is compensating you for roughly 40 hours a week. Yeah. The expectation is full-time commitment for each, even if you manage it in less time. And whether they're W-2 jobs or...

1099 contracts, that's not really the main point. The core idea is getting paid for full time work by more than one place. And the goal, importantly, is doubling or tripling your income without working insane hours. Yeah. Nobody wants that 100 hour work week. Right. Delaney called that literal hell. So efficiency is everything. Which leads us right into the big question. How does AI make this possible?

Or at least make it easier. Okay, yeah. The AI angle. This is where it gets really interesting for our listeners. So AI helps in basically two main areas, right? Within the job itself, making you more efficient. And during the job search process, getting the jobs. But before jumping to AI solutions, Delaney stressed something important. What's that? You got to understand where your time actually goes now. Keep a time journal. Track your tasks. Self-awareness first.

Makes sense. Yeah. Because AI isn't always the answer. Exactly. Sometimes it's about changing a process or just stopping doing something that doesn't add value. Like his example of maybe scrapping a weekly market report if nobody really uses it. Right. Don't automate something you shouldn't be doing in the first place. Solid advice. So after you've done that homework, then you can look at AI tools. And Delaney estimates that for a lot of jobs, maybe 70, 80 percent, excluding really deep technical stuff like coding, a big chunk of the work is...

well, moving information around, reformatting it, summarizing it. Stuff AI is pretty good at. Exactly. So his advice is default to asking, could an AI tool do this? Just build that habit. Yeah. And use tools...

You know, ChatGPT is his favorite, but Gemini, Claude, they all work. And how should people prompt these tools? Treat it like talking to a helpful colleague. Just explain the problem clearly. Dump your thoughts even. The AI can usually figure it out. He gave an example, right? Cutting down report writing. Yeah, like pasting meeting notes into ChatGPT and saying, summarize the key decisions, action items, and sentiment in bullet points for my weekly report.

He said it could cut report time by like 50%. Wow, okay. That's tangible. And you could even ask the AI what's the best tool for this specific task. It might suggest something more specialized. Good tip. Give it context too, right? The more detail, the better the result. Definitely. Explain your workflow, what you need the output for.

And for the tech-savvier folks, he mentioned creating custom GPTs. You can feed it your company's onboarding docs or knowledge base. So it becomes like a specialized assistant trained on your specific stuff? Exactly. Pretty powerful for getting up to speed or finding info quickly. Okay, but the elephant in the room, security. Using external AI with company data. Especially across multiple jobs, that feels risky. Huge question. And Delaney is upfront about it.

Job stacking itself has risks. Using external tools with company data, that's often a gray area, or maybe even a direct violation of your contract. So what's the advice? It comes down to your personal risk assessment. How likely are you to get caught? What happens if you do? A calculated risk, basically. Yeah. And he pointed out, companies are inconsistent. Some block chat GPT but allow Gemini or Microsoft Copilot. So you've got to see what's available, what the company culture is like. Use what's allowed, if possible.

But his take is if you're committed to job stacking, you kind of have to find ways to be efficient and that might involve these tools. Right. He did mention the chat GPT setting to opt out of data training, which helps a bit. But not foolproof. Not foolproof. He also said in the past he'd sometimes forward docs to his personal email, use AI on his own machine, then bring the results back.

OK, so workarounds exist, but they come with their own risks, too. Definitely. It's a constant balancing act. All right, let's pivot. How does AI help actually get these jobs? The job search part. OK, yeah, because not everyone's ready to stack immediately. Maybe the first step is just getting one good remote job. Right. Replace an in-person gig. So elevated text framework, get interviews, turn interviews into offers, then get efficient in the role.

AI is massive in that first step getting interviews. How so? Recruiters are using AI too. Totally. Think about it. 500 plus applications per job sometimes. Recruiters aren't reading all those. AI does the first pass. It's like Google search. If you're not on the first page of results, you're invisible. So the challenge is getting your application seen by the recruiter's AI. Exactly. Making sure you show up in their search results. And how do you do that? A big part is targeting the right job titles.

Delaney found a strong link between the number of postings for a title and how fast people get interviews. Interesting. Like volume matters. Yeah. His example was director of engineering versus engineering manager. Director might pay more, but there are way more manager jobs open. So apply for manager roles. Potentially. Yeah. It's like sales, more prospects mean more chances, even if the average deal size is a bit smaller.

So using AI tools to apply to a lot of relevant jobs. He talked about applying to maybe 2,000 engineering manager roles in a month. 2,000? How is that even possible? AI application tools combined with optimization.

Your resume and LinkedIn have to be packed with the right keywords for the target title. It's like SEO for your career. You're reverse engineering the recruiter's algorithm. So you need an AI-friendly resume. What does that mean exactly? It means using the keywords that those applicant tracking systems, the ATS software recruiters use, are scanning for.

And formatting it simply so the machines can read it easily. No fancy graphics or columns usually. Keywords and simple format. And Elevated Tech actually pairs AI tools with a human assistant for their clients to hit those high volumes, like 500 applications a week. Wow. Okay, it's a numbers game then. Absolutely. If, say, 100 applications gets you an interview, 2,000 applications means 20 interviews.

Even if you're not a perfect interviewer with 20 shots, you're likely to land something. The goal is like five interviews a week consistently. That's a very different approach than carefully crafting a few applications. Totally different mindset, volume and optimization. Now, we should probably touch on the legal side again and maybe the ethics for some people. Is job stacking actually legal? Good question. Delaney's understanding as of early 2025 is there's no specific U.S. federal law against it.

He mentioned the FTC's move against non-competes as maybe showing a shift towards employee power. But state laws could differ. Yeah. And contracts. Definitely check your state laws. And yes, almost certainly your employment contract will have clauses against outside work or requiring disclosure. That's standard. So you could be violating your contract. Most likely, yes. Though Delaney made the point that lots of senior execs have board seats or side investments. So enforcement can be

selective sometimes. Hmm, interesting point. What's the main risk then? Getting sued? Probably not, unless you're working for direct competitors and spilling secrets. That's serious. But for just holding two unrelated jobs, the main risk is getting fired.

from one or maybe both jobs okay getting fired which sounds bad it does but Delaney reframes it in today's market even loyal single-job employees get laid off right and then they have zero income potentially for months true layoffs are common so compare that with job stacking if you lose one job you still have income if you somehow lose both to ache which seems less likely are you really worse off financially than the person laid off from their single job with no backup

Maybe not. That's a different way to look at the risks, kind of hedging your bets against layoffs. Sort of. He also mentioned the bigger picture economic uncertainty. Ray Dalio's stuff about the changing world order, AI automation like Waymo replacing drivers in Austin. Yeah, the future feels uncertain for many jobs. So having that extra income and savings from job stacking.

It could be a crucial buffer against whatever comes next, whether it's economic downturns or jobs getting automated away. Okay, that makes a lot of sense strategically. So for listeners who are intrigued, maybe not ready to jump into three jobs, but curious, what are the first steps? Well, first, distinguish between just curiosity and actual commitment.

Delaney says it's not always easy, even with AI. Interviewing takes real effort. Right. It's still work. The absolute crucial first step is get crystal clear on your why, what's your motivation, what outcome do you want? Delaney's was that $500 across three roles. That was his North Star. Having a clear goal. Essential. Then a practical second step. Learn how to make that AI-friendly resume we talked about.

He reckons mastering that gets you like 80% of the way there for the initial job search phase. OK, focus on the why and the resume. Got it. And just before I move on, a quick note for everyone listening. If you're finding this deep dive valuable, please take a second to like and subscribe to AI Unraveled on Apple Podcasts. It genuinely helps us keep the show free and bring you more content like this. Yeah, those ratings and subscriptions make a big difference. OK, so back to Delaney's timeline.

How fast did this happen for him? Good question. He went from the $80 job to adding the $160 K-1 within about three months of starting to apply seriously. Three months. That's pretty quick. Then, and this is important, he took about two months off from applying for the next job. Oh, wow.

Why? To really settle into the new $160K role, build relationships, understand the work, build social capital. He stressed being a good employee is key. You can't just phone it in. Right. Build trust, deliver value. That's crucial for making this sustainable. Exactly. Then after those two months, it took another three months or so to land the third job, the $150K one. Okay. So maybe eight months total from starting the search to having all three. But with that pause in the middle. Roughly, yeah.

But he cautions it varies. The market's tough. He said he went through like 10 or 12 final round interviews for that last role. Wow. So persistence is key, too. Definitely. And he suggests that while three jobs work for him, it's intense. For most people, maybe two jobs is more realistic and manageable long term. Makes sense. What kind of fields does this work best in? He was in product management.

Yeah, tech roles are common, software development, QA, cybersecurity, but also things like sales, marketing management, client success, accounting, finance. It's a wide range. He thinks it's theoretically possible in almost any field, really. The easier it is to systematize or automate parts of your work, the easier it is.

Less customer facing stuff often helps. Although he mentioned even sales roles are being juggled creatively. Yeah. But again, always comes back to building trust and social capital in each role. Be good at your jobs. Absolutely. So how do you track if you're on the right path? What are the metrics? The number one KPI, he says, is your weekly interview rate. How many interviews you're getting each week? Exactly.

Exactly. Aim for two or three per week consistently. That shows your application strategy is working. And what about rejections? Those can be discouraging. His advice: ignore them. Or even see them as a good sign. It means you're active, you're in the game.

Focus purely on the interview rate. If you get enough interviews, offers will eventually come with practice. OK, focus on the positive indicator interviews landed. Right. Elevated tech actually tracks this stuff. They look at success rates from AI applications versus easy apply versus filling out long forms on company sites. And what do they find? Interestingly, about a 50/50 split in effectiveness.

The easy applies have more volume but more competition. The longer applications have less competition but take more time. So it's a trade off. Makes sense. But the core message is consistent interviews lead to offers if you keep practicing. Exactly. It's a process. Well, this has been incredibly insightful. The people are inspired and want to learn more from Delaney's company. Yeah, definitely. You can check out Elevated Tech. Their website is elevatedtech.us. Elevatedtech.us. Right. They have a free community. People can join, get resources.

And they also offer done-for-you services if you're busy and want help with the application process. And Delaney's active online, too. Yeah. On Instagram, he's at DelaneyWilliam. That's DelaneyWilliam underscore. He's on YouTube, too. Great. Lots of ways to follow up. Absolutely. And a huge thank you for breaking all this down. Really fascinating stuff. My pleasure. It's definitely a strategy that challenges traditional career thinking. It really does. And for everyone listening, one final thing before we wrap up.

If you're looking to advance your career, maybe get certified in areas relevant to these high-paying remote jobs, check out the JamGet app. JamGet Tech. Yeah, D-J-A-M-G-A-T-E-C-H. You can use it to study and ace up to 50 different certifications. It's a great way to boost your skills and resume. The download links are right there in the show notes. Nice resource. Definitely worth checking out. So as a final thought for you or a listener, think about this.

Even if full-on job stacking isn't for you, how could you apply just one small piece of this? Yeah, like one efficiency hack. Using AI for one task. Exactly. What's one thing you could try to automate or optimize this week just to see how it feels, how it works? Something to think about. Thanks for tuning in to this deep dive.