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.
- 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.”
- 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 A slow dev cycle might trace back to outdated deployment practices.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.
- 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.
- 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.
- 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.
