Tuesday, August 5, 2025

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...