What I Learned Running Product at Travelocity That Still Applies to Small Business

I once ran the product for Travelocity's entire Canadian platform. Millions of users. Thousands of flights, hotels, and packages flowing through the system every day. A team of engineers, designers, and analysts all building toward the same goal: make it easier for people to book travel.

You'd think the biggest takeaway from that experience would be something about handling massive scale, or managing enterprise budgets, or navigating corporate politics. And sure, I learned plenty about all of that. But the lessons that stuck — the ones I use every single week working with small business owners — are surprisingly simple.

Nobody Cares About Your Features. They Care About Their Problem.

At Travelocity, we had a wall of features we could build. Fancy filters. Loyalty dashboards. Social sharing tools. The list never ended. And every stakeholder had a pet feature they were convinced would change everything.

But here's what actually moved the needle: understanding the exact moment a customer got stuck. Someone searches for a flight to Vancouver. They find one they like. They click to book. And then — three extra form fields they didn't expect. They bail. That's it. That's the whole problem. Not a missing feature. A moment of friction.

Small businesses fall into the same trap. I hear it all the time: "I need an app that does X, Y, and Z." And when I ask why, the answer usually comes down to one specific pain point that doesn't require X, Y, or Z to fix.

Before you build anything, identify the exact moment your process breaks. Not the category of problem. The specific moment.

Measure What Matters, Ignore What Doesn't

Travelocity had dashboards for everything. Page views, click-through rates, conversion funnels, session duration, bounce rates — you name it, someone was tracking it. And most of it was noise.

The metrics that actually drove decisions were shockingly few. Conversion rate from search to booking. Average revenue per booking. Cart abandonment rate. That was basically it. Everything else was interesting but didn't change what we did.

I see the same pattern with small business owners. They'll spend hours looking at website traffic or social media engagement numbers and have no idea whether those numbers connect to revenue. If you run a service business and you're tracking Instagram likes instead of lead-to-close rate, you're watching the wrong screen.

Pick two or three numbers that directly connect to money in or time saved. Track those. Everything else is a distraction until those numbers are where you want them.

Ship Something Small, Then Fix It

We never launched a perfect product at Travelocity. Not once. Every major feature went out the door knowing it wasn't finished. That sounds reckless until you realize the alternative: spend six months building something perfect that turns out to solve the wrong problem.

The pattern was always the same. Ship a basic version. Watch how people actually use it. Fix the real problems that show up — not the ones you imagined in a conference room.

I built a proof of concept for CivicTalent — an AI-powered recruitment matching portal for local government — over a single weekend. It wasn't polished. It was functional enough to show city clients what was possible. That working demo is what moved the project forward, not a 40-page requirements document.

When I work with small business clients now, I push hard for the same approach. Don't spend $25,000 building your dream app. Spend $5,000 building something that works. Use it for a month. Then we'll know what to build next because we'll have real information instead of guesses.

The Best Technology Is the One People Actually Use

We tested a beautiful new booking interface once. It was objectively better — faster, cleaner, more intuitive. We were proud of it. Users hated it. Not because it was bad, but because it was different. They knew where things were in the old version. The new version made them think.

This lesson hits harder in small business than it does in enterprise. If you hand a team of three a complex new system, you haven't automated anything — you've created a training problem. I recommended Smartsheet for an airfield lighting distributor specifically because the team already understood spreadsheets. The transition was practically invisible. That's why it worked. That's why they actually saved 30% of the time they used to spend on paperwork.

When I evaluate tools for a client, "will your team actually use this every day" matters more than any feature list.

The Takeaway

Running product at Travelocity taught me that good software decisions come from watching real people hit real problems — not from feature wishlists or technology trends. That's true whether you're serving millions of travelers or running a ten-person operation.

The scale changes. The principles don't. Find the friction. Measure what matters. Ship small. Build for adoption, not admiration.

If you're trying to figure out where technology actually fits in your business — not where a vendor tells you it fits — that's the conversation I have every day. [Book a free conversation](https://outlook.office.com/owa/calendar/Brincore@brincore.com/bookings/) and let's talk about your specific situation. No pitch, no pressure.