Episode 29
How to Choose Booking Software That Fits How You Actually Operate, with Devin Spann
Your booking software isn't just another tool. It's the foundation your business runs on.
Learn how to evaluate any booking platform against what your operation actually requires.
In this episode of the Tour Operator Growth Podcast, Nikki and Greg are joined by Devin Spann, who spent years as a product manager at Resmark turning operator feedback into features used by tour businesses around the world before moving into sales. This isn't a product demo or a pitch to switch. It's a framework for choosing software you won't outgrow.
Devin explains why every platform handles the basics, and why the real difference is how easily you can run your business on top of them. He shares what polished demos hide, the hard questions to ask a sales rep (data access, roadmaps, integrations), and why bringing a must-have list saves everyone weeks of wasted calls. The conversation covers which capabilities shift from nice-to-have to essential as you grow, like user roles, automated pre-trip emails, and integrated waivers, and why a platform that also powers your marketing, from SEO to conversion rate optimization, becomes invaluable at scale. They wrap with practical advice for migrating off a system you've outgrown and Devin's five-year test: choose a company that listens, responds, and treats you like more than a number.
Frequently Asked Questions
-
How do I know if I'll outgrow a booking platform?
Every system handles the basics: bookings, waivers, confirmations, payments. Look past those to how easily you can run your whole business on it, and whether the company truly understands your industry from beginning to end.
-
What does a software demo not show me?
Demos are polished and rehearsed. They rarely reveal how the system performs at real volume, how your data is stored and accessed, or what's on the product roadmap. The gaps usually surface about six months after implementation.
-
What questions should I ask during a demo?
Ask the hard ones: What happens to my old data? How long is it stored and who can access it? What's on your roadmap? Which of my current tools could this replace? It's also fine to leave questions as homework and let the rep come back with real answers.
-
Should I prepare anything before evaluating software?
Yes. Bring a list of core must-haves and a separate nice-to-have list. If a platform can't meet a must-have, you'll find out on call one instead of week three.
-
Which features become essential as I grow?
User roles and permissions, automated pre-trip email cadences, integrated digital waivers, and marketing capabilities like SEO and conversion rate optimization. They feel optional when you're small and critical at scale.
-
Is an all-in-one platform better than separate integrations?
If an existing product covers 80% of what you need, go with it. And if juggling disconnected tools eats more than 20% of your time, that's the signal to consolidate into one connected system.
-
How do I make switching booking systems smoother?
Decide how much historical data you actually need (often just the last couple of years), ask about data formats early, and use the migration as a chance to drop processes that exist out of tradition rather than need.
-
What's the five-year test for choosing software?
Choose a company you feel at peace with. Are they responsive? Do they listen to feedback and actually deliver on it? Do you talk to real humans? That culture shows up in how the software improves over time.