IT Engineering and People Leader with a Passion for Managing IT Infrastructure, Cloud, and DataCenter Operations - I Teach People How To Break Into Tech And Grow Their IT Career

I am an IT executive focused on closing the gap between technical skill, leadership readiness, and real-world execution in enterprise environments.

With more than 25 years of experience, I’ve led IT infrastructure, operations, cloud platforms, and modernization initiatives across complex public-sector and private-sector organizations—where reliability, accountability, and mission impact are non-negotiable.

I currently serve as Deputy CIO for IT Infrastructure &amp; Operations supporting the Illinois Department of Children and Family Services (DCFS). In this role, I oversee large-scale infrastructure and cloud operations, IT service management (ITSM), operational resilience, and modernization efforts that support mission-critical systems serving vulnerable populations statewide.

My background spans infrastructure strategy, cloud transformation, data center modernization, cybersecurity alignment, program and project delivery, vendor management, and service delivery optimization. I’m often brought in to stabilize environments, modernize legacy systems, reduce technical debt, and design governance models that align technology execution with organizational mission.

As a U.S. Navy Veteran, MBA, and PMP, my leadership style blends discipline, clarity, and adaptability. I believe strong IT organizations are built through people-first leadership, clear decision-making, and intentional talent development. Mentorship is a core part of my work—helping professionals move from capable operators to trusted leaders.

I’m particularly interested in how organizations define, measure, and develop real-world IT capability as cloud, automation, and AI continue to reshape the workforce.

Looking ahead, my focus is continued impact at the IT executive level—including CIO, Head of IT, and enterprise technology leadership roles—where I can influence strategy, drive transformation, and ensure technology functions as a true mission and business enabler.

Follow me if you’re navigating the jump from operator to leader in IT, infrastructure, and enterprise environments—and want clarity on what leadership readiness actually looks like.

Dean Cantave, MBA

In 2021, I applied for over 600 positions.
 
Let me say that again. Six. Hundred.
 
I had 25 years of IT experience. A PMP. An MBA. A proven track record managing teams, infrastructure, digital transformations.
 
And for an entire year, I could barely get a callback.
 
I sat in interview after interview where I explained concepts with clarity, demonstrated leadership thinking, showed exactly how I’d add value. And still heard: “We went with another candidate.”
 
That year broke something in me. And then it rebuilt something better.
 
Because what I realized is: the system isn’t designed to find the best person for the role. It’s designed to reduce risk. To check boxes. To filter people OUT, not invite people IN.
 
And once I understood that, I stopped playing by the rules the system gave me. I started playing by the rules the system actually runs on.
 
Relationships. Reputation. Positioning. Making my value visible before I ever submitted an application.
 
Within a few years, I went from 600 rejections to a CIO role.
 
Not because I became more qualified. Because I became more legible to the people making decisions.
 
If you’re in that 600-applications season right now—I see you. I’ve been you.
 
And I’m going to teach you what nobody taught me: how the system actually works.
 
Follow. This is what I’m here for.

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This is the difference most hiring and training models miss.

You don’t build judgment by memorizing— you build it by making decisions repeatedly, seeing outcomes, and adjusting.

Looking back, what decision finally “clicked” for you after enough reps—and how long did it take?

Deputy CIO | IT Infrastructure & Operations | Cloud & ITSM | Executive Leader Focused on Systems Modernization and Workforce Readiness

The best hire I ever made had zero certifications.
 
The worst hire I ever made had six.
 
One could communicate, lead, and solve problems under pressure.
 
The other could pass exams.
 
Credentials get you in the pile. Demonstrated competence gets you the offer.

The hiring process has 6 rounds of interviews, 3 panel reviews, and a take-home project.
 
The average time-to-hire is 44 days.
 
And 46% of new hires are still considered failures within 18 months.
 
The process isn’t thorough. It’s just slow.
 
Slow and effective are not the same thing.

The skill that separates a $70K IT professional from a $200K executive is not technical.
 
It’s communication.
 
Not “soft skills.” Not “being a good presenter.”
 
I mean: the ability to take a complex technical problem and translate it into language that makes a decision-maker act.
 
I’ve seen brilliant engineers get passed over for promotions because they couldn’t explain their own impact in a 30-second conversation with a VP.
 
And I’ve seen average engineers get promoted because they could walk into a room and make leadership understand exactly what was at stake, what the options were, and what they recommended.
 
The difference wasn’t knowledge. It was visibility.
 
The person who communicates well becomes visible. The person who’s visible gets opportunities. The person who gets opportunities advances.
 
The person who’s brilliant but invisible? They stay where they are. For years.
 
This is the single most undertaught skill in tech. And it’s the one that moves the needle most.
 
If you can learn to translate complexity into clarity—you’ll outrun people with twice your experience.
 
Start here: the next time you explain a technical concept, ask yourself—could a VP who doesn’t understand the technology still make a decision based on what I just said?
 
If the answer is no, you’re not communicating. You’re narrating.
 
Follow for more of this. I’m teaching what actually gets you promoted.

Dean Cantave, MBA, PMP

The Resume Era is over.
 
We just haven’t admitted it yet.
 
Think about what we’ve updated in the last decade:
 
We’ve modernized how we manage projects. We’ve transformed how we build software. We’ve reinvented how we store, analyze, and move data. We’ve adopted AI across almost every enterprise function.
 
But the system we use to identify, evaluate, and hire talent?
 
It still runs on a one-page document that a candidate writes about themselves.
 
Let that sit for a second.
 
We’ve updated every system in the modern enterprise except the one that matters most: how we connect talent to opportunity.
 
The result?
 
Companies spend $4,700 per hire on average. Time-to-fill sits at 44 days. And nearly half of all new hires are considered failures within 18 months.
 
That’s not a talent shortage. That’s a talent identification failure.
 
What’s replacing it isn’t a better resume template. It’s a fundamentally different standard:
 
Demonstrated competence.
 
Not what you claim on paper. What you can prove in practice.
 
Not credentials. Capabilities.
 
Not years of experience. Evidence of impact.
 
The companies that figure this out first will dominate the next decade of talent acquisition. The professionals who understand this first will have a massive advantage.
 
The Resume Era is ending. The Demonstrated Competence Era has begun.
 
I’ve been teaching this for months. Now I’m building the infrastructure to make it real.
 
Follow if you want to be early.

I’ve worked in IT for over two decades.
 
I’ve hired over 100 professionals. I’ve sat on more hiring panels than I can count. I’ve reviewed thousands of resumes.
 
And I can tell you something that most career advice won’t:
 
The person who gets the job is almost never the most qualified person in the room.
 
They’re the most legible.
 
Meaning: the hiring panel can see their value immediately. Their experience is framed in outcomes, not tasks. They speak the language of the room they’re trying to enter.
 
The person with 6 certifications who talks about what they “know” will always lose to the person with 2 who talks about what they’ve “done.”
 
I know that’s frustrating to hear.
 
You’ve invested time and money into building skills. You’ve studied. You’ve prepared. And you’re still getting passed over.
 
It’s not because you’re not good enough.
 
It’s because nobody taught you the rules of the game you’re playing.
 
That changes this month. For the next 20 days, I’m going to share exactly what I see from the hiring manager’s chair—what works, what doesn’t, and what nobody else is telling you.
 
Follow along. This is the career education the system never gave you.

I’ve sat on hundreds of hiring panels throughout my IT career.
 
Not once did I start with the candidate’s certification list.
 
After 25 years of hiring, managing, and promoting professionals across some of the most complex IT environments in the country, I can tell you exactly what separates the person who gets the offer from the person who doesn’t.
 
It’s not what most people think.
 
Swipe through → I broke it down into the 7 things that actually get you hired.
 
If you’ve been applying, interviewing, and hearing nothing back—your skills probably aren’t the problem.
 
Your positioning is.
 
Save this carousel. Share it with someone who needs to see it.
 
I’m Dean Cantave. CIO. Building GetSkillsGap.ai to teach what the system won’t.
 
Follow for the hiring manager’s perspective. Every week.

Hiring Managers Perspective

I’ve hired over 100 people in government IT.
 
Not once did I start with the certification list.
 
Here’s what I actually look for when a resume crosses my desk—swipe through for the 7 things that actually matter.
 
Save this. Share it with someone who’s been applying and hearing nothing back.
 
Follow for the hiring manager’s perspective. Every week.

7 Things That Get You Hired

There are 3 gaps keeping qualified IT professionals stuck. None of them are what you’ve been told.
 
Swipe through → I break down each one and what to do about it.
 
Save this. It’s the map nobody gives you.

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Got a DM this morning that stopped me:
 
“Dean, I’ve been applying for 8 months and your post about 600 applications made me feel like someone finally understands.”
 
If that’s you—stay close. What I’m sharing this month could save you a year of guessing.
 
(If you got value from this morning’s post, share it. Someone in your network needs to see it.)

A resume cannot show how you think.

It cannot show:

How you solve problems
How you respond to uncertainty
How you make decisions

It can only show where you have been.

But employers are hiring you for what you will do.

Not where you have been.

This disconnect is one of the core structural flaws in hiring.

The future will favor professionals who make their thinking visible.

My first real tech job threw me into the deep end. It was the best thing that ever happened to me.
 
When I got my first project management job at Aon, I had no idea what I was doing.
 
I’m not being humble. I genuinely had no idea.
 
I walked into one of the most complex IT environments I’d ever seen. Huge DataCenter in Lincolnshire, Illinois. Hosting applications for companies like McDonald’s and a dozen other large companies at a time when application hosting was a thing.
 
My job? Manage infrastructure projects from kickoff to deployment.
 
I had to learn how to kick off a project. What teams to engage. How to schedule stakeholder calls. How to navigate stage-gate documentation. How to communicate with teams who knew infinitely more than I did technically.
 
Every single day, I was learning faster than I could keep up.
 
And that’s exactly what made it the most important job of my career.
 
Because Aon didn’t teach me technology. It taught me how to operate inside complexity.
 
How to manage ambiguity. How to communicate across teams. How to earn credibility when you’re the least experienced person in the room.
 
No certification taught me that. No course covered it. I learned it by being thrown into the deep end with professionals who were operating at a level I didn’t even know existed.
 
That’s the training gap.
 
Not “I don’t know enough.” But “Nobody showed me how to operate inside the system.”
 
If you’re early in your IT career and you feel like you’re drowning—that’s actually the signal that you’re in the right place. The discomfort IS the training.
 
Follow for more. I share what 25 years in tech actually taught me—not what the textbooks say.

Over 900 interviews. Zero offers.

Not in a month. Not in a year.

Over a span of five years.

I started in IT in 2006 as a contractor in Chicago — helpdesk, hardware deployments, break-fix work. I was hungry to grow but had no roadmap. No mentor. No access to real training. Just the job in front of me and the ambition to do more.

Between 2016 and 2020, I had over 300 interviews without a single offer.
In 2021 alone — 600 more.

Let me give you three specific examples of what that actually looked like:

Interview #1. A Managing Director role. Seven rounds. The recruiter told me I was the only candidate out of everyone they submitted who made it that far. I went all seven rounds. No offer. No call. No email. I had to reach out myself just to learn they'd moved on.

Interview #2. A Director role. Three rounds. All positive feedback. VP in the final round. They came back and said they didn't want to offer me the Director role — but they'd like to offer me a Senior Manager role instead.

They called me in for one position and tried to hand me something lesser.

Interview #3. A Director role at a bank. Two conversations, then they moved on internally. Two months later, they called me back. Their preferred candidate had received a counteroffer and stayed at his current company. They brought me back in, ran me through more logistics, more scheduling, more time. Then didn't make me an offer.

I was the backup to the backup.

A white Executive I respected told me directly that he believed race was a factor in some of what I was experiencing.

I've always been aware of how racism operates in hiring. I don't have control over that.

What I do have control over — is what comes next.

Here's what I know after 25 years in this industry:

Companies want the best people. Full stop. And the best people aren't always finding their way through.

Not because talent doesn't exist. Because the gap between what candidates demonstrate and what companies actually need has never been wider.

That gap is what I'm building SkillsGap to solve.

Better trained candidates. Better equipped companies. A system that actually works for both sides.

AI is now the great equalizer. The tools exist. The access is there. The excuses are gone.

I'm writing a book on all of this — the broken hiring system, the skills gap, and what it takes to win in the age of AI.

I'm starting that project this week.

Link to get notified when it drops is in the comments.

If this resonates with you — follow. I'll be sharing these conversations on the future of work every week.

Most Americans don’t realize a quiet shift in economic policy just happened.

In 2025, as part of the “Big Beautiful Bill” the U.S. Congress passed a tax bill that created something called “Invest America Accounts.”

The idea is simple but powerful.

Every child born between 2025 and 2028 will receive $1,000 invested in the stock market at birth.

The money goes into a long-term investment account tied to index funds. Families can add to it over time, and by the time the child reaches adulthood, it could grow significantly through compound returns.

The goal behind the policy is philosophical as much as it is financial.

If more Americans own capital, they become participants in the economic system rather than observers of it.

In other words, the idea is to make every child a shareholder in the American economy.

It does raise some interesting questions from my viewpoint:

• What happens when an entire generation grows up owning stocks from birth?
• Does this strengthen capitalism by broadening participation?
• Could this help close wealth gaps over time?
• And will financial literacy become just as important as traditional education?

We often talk about the skills gap in the workforce, but there is also a capital ownership gap in the economy. 

Policies like this are trying to address that.

Whether you agree with it or not, it’s one of the more interesting economic experiments happening right now.

And it officially launches in the summer of 2026.

Curious what others think about this.

Your manager doesn’t promote the hardest worker.
 
They promote the person whose value they can explain to THEIR manager.
 
If your work is invisible to the decision-makers above you, it doesn’t exist in the system that decides your career.
 
Communication isn’t a soft skill. It’s a visibility strategy.

A hiring manager is about to make an offer.

They have two candidates.

Candidate 1
Works at a well-known company
Strong resume
Safe background

Candidate 2
Less recognizable company
Less polished resume
But demonstrates stronger thinking in the interview

Who gets the offer?

Usually Candidate 1.

Not because they are more capable.

Because they are safer.

Hiring managers are not rewarded for discovering hidden capability.

They are rewarded for avoiding visible mistakes.

This is how capability gets filtered out of the system.

This is why the hiring model must evolve.

The one thing that has been on my mind over the past few years is that an era is coming to an end.

It’s sad honestly.

You all know what I’m talking about.

Our parents.
Our grandparents.
Our elders.

The people who were our heroes. Our rocks. The ones we looked up to for strength, for guidance, and for an example of what it meant to live with purpose.

When I think about legacy, this is what I think about.

Leaders like Rev. Jesse Jackson Sr. — men and women who lived lives of sacrifice. People who didn’t pursue recognition, but pursued justice. People who woke up every morning with a singular purpose: to serve others and to move their people forward.

They embodied a form of excellence that wasn’t curated for attention or amplified by algorithms. It was built through courage. Through conviction. Through sacrifice.

They stood in places where standing came at a cost.

This generation is slowly becoming history — not just in age, but in presence.

Many of us had the privilege of growing up in the 70s, 80s, and 90s, witnessing a culture rooted in pride, dignity, and responsibility. We saw leaders who believed deeply in something bigger than themselves. Leaders who carried the weight of a people on their shoulders and chose to carry it anyway.

Rev. Jesse Jackson Sr. now joins that pantheon of giants — those who volunteered to take the heat so that others could walk in the light.

His life forces us to confront an uncomfortable but necessary question:

Who picks up the mantle now?

Legacy is not something we admire from a distance. It is something we are called to continue.

May we honor him not only with our words, but with our lives.

Rest in power, Rev. Jesse Jackson Sr.

The resume is not a capability document.

It is a marketing document.

Its purpose is to present you in the best possible light.

Not to objectively measure what you can do.

This is why resumes often fail both employers and professionals.

Employers cannot see true capability.

Professionals cannot differentiate themselves based on reality.

Two people can have identical resumes and completely different execution ability.

Yet the hiring system treats resumes as truth.

The future will move toward demonstrated capability — not described history.

Unpopular opinion from a CIO:
 
Most certifications are a tax on people who don’t have access to mentorship.
 
Think about it.
 
If you had a mentor in IT leadership—someone who could tell you exactly what skills matter, how to position yourself, and how hiring actually works—would you spend $3,000 on a certification?
 
Probably not.
 
You’d invest that time in building relationships, doing visible work, and learning how to communicate your value.
 
But most people don’t have that mentor. So they do what the system tells them: get another cert. Take another course. Add another line to the resume.
 
And the cycle continues.
 
I’m not anti-certification. Some are genuinely valuable. The PMP changed my career.
 
But I am anti-certification-as-a-substitute-for-career-strategy.
 
The cert gets you in the pile. It doesn’t get you the offer. What gets you the offer is your ability to walk into a room and make decision-makers see your value in 5 minutes.
 
That’s a skill. And it’s teachable. But almost nobody is teaching it.
 
That’s the gap I’m here to close.
 
Follow if you want the strategy, not just the credentials.

AI was supposed to save us from endless meetings.

Instead, it's making the problem worse.

Teams are drowning in calls and syncs. Not because there's too much to discuss, but because there are too many people involved.

Here's what actually happens:
- The "quick stand-up" turns into a group therapy session.
- Two people drive the convo, six stare at their screens.
- You align... then schedule another "alignment" for later.

Most leaders blame calendars. But this isn't about scheduling. It's about structure.

The more teammates you add, the more conversations you need. AI cranks up individual productivity, but it doesn't reduce the number of people who need to check in with each other. The result? The number of meetings explodes.

It's basic math. Most companies haven't done the math.

AI tools won't save your calendar. Smaller teams will. Cut your group in half and watch your schedule clear up.

Fix your team size. Your time comes back.

What's one meeting on your calendar this week that could have just been a message?

Options Clearing Corporation, The

Principal Infrastructure Engineer

Keller Soccer Association

I have serve as a commissioner for various age groups including U11+G , U9/U10G commissioner and currently serve as the scheduler and field maintenance manager.

Board Member

Associate Principal

Infrastructure Manager

Lead Middleware Administrator

As a part of my responsibilities, I liaison between engineering and development to ensure adequate and proper communication. Documentation of expected system configurations, automated shakeout of environments upon deployment and application development are part of my day to day.

Environments Developer - Consultant

MyAlarmPermit.com

Tap N Spend

GameStop

Agile/PMO Manager of Online Technology

URDCaster

Founder

Handmark

Managed a team of software engineers to architect, designed enterprise software products/operating systems. Wrote product requirement documents, implemented and tracked development timelines, negotiateed feature sets with the development leads and product. Generally managed a group of software developers/engineers. Relied on experience and judgment to plan and accomplish goals.

Continued to develop code and mentor developers.

Software Engineering Manager

Team Lead/Software Developer

Travelocity

Lead Software Developer

Sabre Holdings

Senior Software Developer

Middleware enthusiast with an appetite for modernizing legacy technologies. 

Scrum Master/Project Manager with solid experience running co-located and distributed scrum teams/scrum-of-scrums.

Software Development Manager for small business focused on yielding high throughput while resourcing at a low cost.

Lead Software Developer with extensive experience in J2EE, OOAD, TDD and a strong database background.  As a lead I've recently lead teams on multiple continents, including Germany and Argentina. My next career step is management.

Specialties: Software architecture, database interfaces, OOAD.

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