Sunday, August 31, 2025

The Story of Labor Day: A Holiday Built by Workers, Carried by Tradition

On a warm September morning in 1882, the streets of New York City were alive with an unusual energy. Workers, many in their union sashes and Sunday best, gathered with families and friends near City Hall. Bands struck up tunes, children waved flags, and crowds lined Broadway to watch what would become the first Labor Day parade.

 

That day, thousands marched shoulder to shoulder, not for protest or riot, but for recognition. They wanted the city, and the nation, to see the dignity in their labor and the strength of their unity. Some say the idea came from Matthew Maguire, a machinist and union secretary. Others insist it was Peter McGuire, a carpenter inspired by labor parades he had seen in Canada. To this day, no one is entirely sure who thought of it first. Let’s just call it the original “credit-stealing coworker” story.

 

From that spark, celebrations spread. States across the country began setting aside their own labor days. By the early 1890s, the holiday had taken root in the American calendar. In 1894, amid the turmoil of the Pullman Strike, President Grover Cleveland signed it into law: the first Monday in September would be a national holiday. Not just a day off, but a day to honor the men and women whose sweat and determination built the roads, the railways, the factories, and the very backbone of America. And yes, you can thank them for the reason you don’t have to explain to your boss why you are “working from home” on the first Monday of September.

 

Over the decades that followed, Labor Day grew into more than parades and speeches. It became family picnics, neighborhood festivals, and backyard barbecues. It became the last sweet taste of summer before the school year began. And yet, beneath all of that, the meaning has remained steady. This holiday is a reminder that the 40-hour workweek, fair wages, safe conditions, and the right to rest were all won through the persistence of workers who believed their contributions deserved dignity. So next time you clock out at 5 p.m. sharp, you can raise a toast to those folks.

 

Today, work looks very different. Some of us build with our hands, others with our minds. Some work on factory floors, others in digital spaces where the “reply all” button is the most dangerous tool of all. But the spirit of Labor Day calls us to the same truth: every effort matters, every role builds something greater than itself. Just as the laborers of the 19th century fought for balance and fairness, so too must we shape the future of work, whether it is ensuring flexibility, protecting well-being, or embracing new tools like technology and AI in ways that lift people rather than replace them.

 

So this Labor Day, as we gather with family and friends, let us carry forward the story begun on that September morning in 1882. It is a story of unity, dignity, and progress, and it is still being written one paycheck, one coffee break, and one backyard burger at a time.

 

Monday, August 25, 2025

Experience, Perspective, and Energy: What Sets Me Apart

Experience, Perspective, and Energy: What Sets Me Apart

When companies look to hire technology leaders, they often search for two things: experience and energy. Finding both in the same person is rare.

 

Over the past 26 years, I’ve built a career that spans system administration, product ownership, and IT leadership. Each role gave me a different lens on technology, business, and people. Together, they formed a perspective that is hard to duplicate.

 

What makes this unique is not just the depth of experience, but the way those roles connect. I know what it feels like to keep servers alive at 2 a.m. I know how to translate business needs into features that developers can deliver. I’ve balanced long-term technical decisions against short-term business pressures. And I’ve led teams where success depended not on my individual output, but on how well others thrived.

 

And while I am not young, my energy often outpaces those who are. That drive doesn’t come from energy drinks or bottomless coffee pots. It comes from passion. I love what I do, and that enthusiasm fuels every conversation, every project, and every challenge I take on.

 

For organizations, that combination matters. It means hiring someone who brings the wisdom of experience, the perspective of multiple roles, and the energy of someone who is still excited to build, lead, and deliver. In a market where depth and passion are both rare, I bring both to the table.

 

Let’s Connect

If you’d like to learn more, you can reach me at www.michaelcronin.info or call me directly at 210-347-1397.

 

From System Administrator to IT Director: Four Roles, Four Perspectives

From System Administrator to IT Director: A Career Told Through Four Roles

I didn’t set out to become a technology leader. In fact, my first role was simply about keeping the lights on. Over the past 26 years, my career has taken me from server rooms to board rooms, from chasing down cables to aligning entire organizations. Along the way, four roles shaped how I think about technology and leadership: system administrator, development product owner, technical product owner, and director of IT.

 

System Administrator: Where It All Began

I can still remember the long nights spent in server rooms, listening to the hum of machines while I tried to figure out why something wasn’t working. As a system administrator, every day was about solving problems as quickly as possible. Servers had to stay up. Networks had to stay secure. Users needed help, often at the worst possible times.


That role taught me one of the most important lessons of my career: reliability is everything. If technology doesn’t work, nothing else matters. Those years gave me discipline, attention to detail, and a respect for the often invisible work that keeps businesses running.

 

Development Product Owner: Learning to Listen

Eventually, I moved out of the server room and into meeting rooms. As a development product owner, my job was no longer fixing systems but listening to people. I had to understand what the business needed and translate that into stories and features for developers.


This was a shift in perspective. I couldn’t solve every problem by myself anymore. My role was to ensure we were solving the right problems. It meant balancing priorities, budgets, and timelines while earning trust on both sides of the table. More than anything, I learned the value of listening.

 

Technical Product Owner: Speaking Two Languages

Taking on the technical product owner role felt like standing with one foot in each world. On one side were the business leaders, focused on strategy and outcomes. On the other side were the engineers, focused on architecture, APIs, and code. My job was to translate between the two without losing meaning.


It wasn’t always easy. Every decision carried long-term consequences. Every innovation had to be weighed against stability. I learned that owning a product meant more than writing a roadmap. It meant owning the responsibility for its health and direction long after the initial launch.

 

Director of IT: Leading with Purpose

When I became a director of IT, the scope widened again. Suddenly, I wasn’t just responsible for systems or products. I was responsible for people. Teams looked to me for guidance, vendors looked to me for decisions, and executives looked to me for strategy.


This role taught me that leadership is not about being the smartest person in the room. It’s about creating an environment where other people can succeed. My success started to be measured not in how many problems I solved personally but in how well the team could operate without me.

 

Looking Back

Each of these roles gave me something I carry with me today. From the system administrator, I learned the importance of reliability. From the development product owner, the value of listening. From the technical product owner, the need to balance vision with reality. And from the director of IT, the responsibility of leadership.

Together, they shaped more than a career. They shaped a perspective: technology only succeeds when people, process, and purpose are working together.

 

Tuesday, August 5, 2025

Seeing the Forest Through the Trees: Product Leadership in a Small Business

In small businesses, product leadership isn’t just about having the roadmap. It’s about seeing the whole landscape, the forest, while also knowing when to zoom in and pull weeds.

 

Most days, I’m the person in the room asking, “Are we solving the right problem?” while also mapping out how we’ll get the fix deployed without blowing up the sprint. I’ve worn the title of VP of IT, Product Manager, Business Analyst, and sometimes just the guy who gets it done. The titles may change, but the core responsibility stays the same: drive clarity, keep the product aligned to the business, and don’t lose sight of the big picture.

 

Here’s how I navigate that balance in the kind of small teams where everyone wears a few hats and the stakes are real.

 

  1. Translate vision into action
    Product leadership in a small business starts by understanding what the business is really trying to achieve. That doesn’t always come through cleanly in requirements or Jira tickets. It often shows up in hallway conversations, customer feedback, or an offhand comment from the CEO.

    My job is to distill that into a plan, not just a feature list, but a sequence of moves that make sense technically, tactically, and financially. I help teams turn “we need automation” into “let’s streamline claim assignment logic based on operating hours and carrier needs.”

 

  1. Connect the dots others don’t see
    When you're close to both the business and the tech, you spot patterns early. A confusing customer workflow might actually be the result of a decade-old product assumption. A slow dev cycle might trace back to outdated deployment practices.   This is where product leadership really shines, pulling together different inputs and recognizing the upstream or downstream impact. It's about pattern recognition, not just backlog grooming.

 

  1. Protect the path forward
    In a small shop, it's easy to get buried in daily fires. Bug here, blocker there, someone needs help resetting a password. But I carve out time to ask “where are we going?” and “are we still on track?” Even if it’s just an hour a week, I revisit the roadmap, double-check priorities, and make sure we haven’t let the urgent crowd out the important. This discipline keeps the team moving with purpose instead of just surviving the day.

 

  1. Talk to people, not just roles
    You can’t lead products effectively without talking to the humans behind the job titles. That means spending time with customer support, sales, QA, and developers, not just in meetings, but in real conversations. What’s hard right now? What’s changing? These chats are gold. They often reveal friction points, new opportunities, or small wins worth scaling. It’s also how you build trust, which makes everything else easier.

 

  1. Make the complex feel simple
    Good product leaders make hard things easier to understand. Whether I’m presenting to execs, coaching a developer through business logic, or helping a customer understand how a feature works, my job is to cut through the noise and communicate clearly. If the room is confused, progress stalls. But when everyone understands the what and the why, the how tends to follow.

 

Final Thoughts

In large organizations, product leadership can mean steering massive roadmaps or aligning siloed teams. In small businesses, it’s more intimate and more personal. You’re close to the work, the people, and the impact. You don’t have layers of abstraction, but you also don’t have as much room for error.

 

Seeing the forest through the trees is a constant exercise. But when you get it right, you’re not just building features. You’re building focus, momentum, and a product that truly supports the business.

 

About the Author

Michael Cronin brings over 30 years of IT experience and 16 years of product and software leadership to his role as VP of IT and Software Development at Claimatic. A hands-on, forward-thinking strategist, he specializes in helping small businesses translate complex needs into clear roadmaps and reliable products. Michael works with companies to realign their IT and product strategies for long-term success.

Cheap and Fast Isn't Always Smart: A Word to Small Business Owners

We’ve all heard it: “Can we get it done quickly and for less?” In small businesses, where budgets are tight and every decision matters, it’s an understandable question. But the truth is, choosing the cheapest and fastest route isn’t always the best move.

 

In fact, it often costs you more in the long run.

 

Here’s what I’ve seen time and again:

  • The “quick fix” turns into a recurring problem that eats up time, energy, and morale
  • The low-cost vendor disappears when support is needed most
  • The shortcut in security leaves the business vulnerable, not just technically, but legally and reputationally
  • The lowest bid doesn’t account for the details that actually matter once you’re up and running

 

Small business leaders are some of the most resourceful people I know. But resourceful doesn’t mean cutting corners. It means making smart, long-term decisions that support the business as it grows.

 

An MVP is a starting point, not a finish line

I’m a big believer in the power of an MVP—a Minimum Viable Product—to prove out an idea or test a concept. It’s a great way to validate direction without over-investing up front. But here’s the key: it’s meant to be a proof of concept, not a permanent foundation.

 

I’ve seen businesses launch with an MVP, get traction, and then try to scale without ever investing in the real infrastructure, design, or process needed for sustainability. That shortcut eventually slows them down.

An MVP shows what’s possible. But if you try to run your business on top of it for too long, you’ll run into problems with performance, security, stability, and support. A smart business leader knows when to evolve from “just enough” to “built to last.”

 

Ask the right questions

When evaluating a fast or low-cost option, I always encourage people to ask:

  • What’s the total cost, not just today, but over the next year?
  • What happens if this doesn’t scale with us?
  • Will this choice simplify our operations or add to the clutter?
  • Are we buying speed, or are we investing in stability?

 

You can move fast.

You can be efficient.
But don’t sacrifice quality and reliability just to save a few bucks or get it done by Friday.

In small businesses, every dollar matters, and every hour of lost productivity matters even more. Choose solutions that grow with you, not ones you’ll have to replace a few months down the line.

 

About the Author

Michael Cronin is an experienced IT and product leader who helps small businesses make practical, forward-looking technology decisions. As VP of IT and Software Development at Claimatic, he guides teams in building stable, scalable solutions that don’t just work today. They work tomorrow, too.

 

What It Really Means to Be an IT Director in a Small Business

When people hear the title “IT Director,” they often imagine a polished office, a handful of department managers, and a lot of meetings about budgets and long-term strategy. That’s a nice picture, but if you’re working in a small business like I do, the reality is very different.

 

Sure, strategy and planning are part of the role. But so is crawling under desks, answering security questions from your CFO, rebooting an old server, writing up policies from scratch, and helping someone recover their accidentally deleted spreadsheet before lunch.

 

Small business IT leadership is hands-on. It’s personal. It’s gritty. And I wouldn’t trade it for anything. Here’s what I’ve learned along the way.

 

  1. The buck stops with you

When something breaks, there’s no “next level of support.” You’re it. Whether it's the network, email, cloud tools, backups, phones, or a random printer jam, the responsibility lands squarely on your shoulders. That pressure can be intense, but it’s also what sharpens your instincts and builds trust with your team.

 

  1. You’re part firefighter, part architect
    Some days are about putting out fires. Others are about designing the systems that will help prevent those fires next quarter. You have to balance the immediate needs of the business with long-term improvements that make life better for everyone. It’s a daily juggling act, but it keeps things interesting. And if you can stay calm in the middle of the chaos, your team will follow your lead.

 

  1. You become the translator
    Business leaders don’t always speak “tech,” and technologists don’t always speak “business.” One of the most valuable things you can do is stand in the gap, translating goals, risks, and ideas so that both sides understand each other.  When people feel heard and understood, progress happens. And as the person bridging the gap, you become essential to decision-making, not just implementation.

 

  1. You don’t get to specialize
    Large organizations have security teams, infrastructure teams, app teams, compliance officers, and product managers. In small businesses, you might be all of those in a single afternoon. That might sound overwhelming, and some days it is. But it also gives you a full picture of how technology works across the business. You’re not boxed into one silo. You get to see and influence the whole.

 

  1. It’s not just about technology
    Being a good IT Director isn’t about knowing every command line or setting. It’s about listening, solving problems, and helping people do their jobs better. Sometimes that means buying new software. Other times it means explaining to someone why a password policy matters or helping them navigate a change. People skills are just as important as technical skills. Probably more so.

Final Thoughts

Being an IT Director in a small business means showing up every day ready to lead, listen, and roll up your sleeves. You don’t have a massive team behind you. But you do have the opportunity to make a real difference every single day.   You’ll be the one they call when the system is down, and the one they thank when things just work. And if you can find a way to blend strategy, service, and steady leadership, you won’t just keep the lights on. You’ll help your business grow in ways no one else can.

 

About the Author

Michael Cronin is an experienced IT leader with over 30 years of hands-on technology work and 16 years guiding teams through growth, change, and challenge. As VP of IT and Software Development at Claimatic, and a trusted advisor to small businesses, Michael specializes in building resilient systems, simplifying complex environments, and helping people get the most from their technology.

 

Wearing All the Hats: Product Ownership in a Small Business with a Small Dev Team

If you’ve ever been in a small business tech leadership role, you know the drill. The job title might say VP of IT or Director of Product, but in reality, you’re part architect, part support desk, part scrum master, QA manager, analyst, your buddy, that guy who gets all the projects done, project manager, security officer, product specialist, and plenty of other titles depending on the hour of the day.

 

That’s the reality for many of us in small to mid-sized companies. We don’t have the luxury of large product teams or multiple layers of management. Instead, we operate in a space where agility, clear communication, and a deep understanding of both the product and the people building it are critical.

 

So, how do you juggle product ownership when you have limited staff and a mountain of business needs? Here’s how I’ve approached it.

 

  1. Prioritize ruthlessly and transparently
    The backlog is always longer than the sprint. I’ve learned to keep a running list of ideas, but only commit to what directly impacts customers or stabilizes the platform. “Nice-to-haves” get logged, but they don’t distract us from what’s urgent or strategic.


More importantly, I make the prioritization process transparent. When stakeholders know why something is being delayed, whether it’s technical debt, dev bandwidth, or a pressing customer bug, they’re more understanding. That trust gives you the space to focus.

 

  1. Talk to developers like peers, not resources
    In a small team, your developers aren’t just coders. They’re collaborators. I keep the conversation open and two-way. We look at what’s feasible, estimate effort together, and talk openly about trade-offs. The more they understand the business context, the better their technical decisions become.

 

  1. Cut technical debt like it’s your job, because it is
    Every bit of commented-out code or workaround adds weight to the team. If you don’t manage it, your developers will spend half their time trying not to break old systems instead of building new value. Recently, we adopted a practice of dating commented code. If it’s still sitting there in 90 days, we delete it. Small habit, big impact.

 

  1. Be a buffer, not a bottleneck
    My job is to absorb noise, clarify what matters, and clear the path. That means having tough conversations with business users who want everything yesterday and shielding the devs so they can focus on building. It also means stepping in when they need help, whether it’s documentation, QA, or just talking through a blocker.

 

  1. Celebrate the wins loudly and often
    When you’re small, every improvement matters. Did we reduce assignment rule complexity by 40 percent? Fantastic. Did we get customer feedback that a new feature saved them hours? Even better. I make sure the team hears that. Momentum is hard to build and easy to lose. Recognition keeps it alive.

 

Final Thoughts

Product ownership in a small business isn’t glamorous. It’s gritty. But it’s also incredibly rewarding. You see the impact of every decision, and you build trust not through titles, but through consistency, clarity, and showing up for your team.

 

Whether you’re leading product in a startup, a niche vertical SaaS company, or a professional services firm, the core challenges are the same. And if you’re wearing all the hats right now, just know you’re not alone.

 

About the Author

Michael Cronin is a seasoned IT and product leader with over 30 years of experience across infrastructure, software development, and technical product ownership. He currently serves as VP of IT and Software Development at Claimatic, where he brings strategy and hands-on leadership to a small but mighty team. Michael specializes in helping businesses bridge the gap between operational needs and product delivery. When he’s not solving complex tech problems, he’s enjoying family time in San Antonio or lending his experience to help others grow.

The Story of Labor Day: A Holiday Built by Workers, Carried by Tradition

On a warm September morning in 1882, the streets of New York City were alive with an unusual energy. Workers, many in their union sashes and...