// SUCCESSION PLANNING

By Michelle Faul

There’ s a shift happening in the outdoor recreation rental industry, and it doesn’ t show up in the trade headlines yet. It’ s quieter than that, visible mostly in the booking patterns, retention rates and revenue growth of a small but growing group of operators who have started running their businesses differently.

What separates them isn’ t fleet size or location. It’ s that they’ ve stopped guessing.

Data Is Becoming the Competitive Moat

For most of the rental industry’ s history, operators have made decisions the way they always have: experience, instinct and a rough sense of what worked last summer. That’ s not a criticism. It’ s how most small businesses operate. But it’ s becoming a disadvantage.

Every booking, cancellation, add-on purchase and seasonal fluctuation contains key data. When compiled, that information tells a story about customer behavior, demand patterns and revenue opportunities that operators can’ t easily read from a spreadsheet. The rental businesses pulling ahead right now are the ones using tools that surface these patterns automatically, not as raw data, but as actionable intelligence.

Which time slots are consistently under booked, and why? Which customer segments return most reliably, and what did their first experience have in common? Which promotions actually changed behavior, versus those that just discounted revenue for customers who would have booked anyway? These are questions that used to require a data analyst. Now, they don’ t.

AI’ s Real Role – And It’ s Not Sending Reminders

There’ s a lot of noise right now about AI in small business software. Many of the claims overstate what the features actually do. For example, automated booking confirmations and reminders are critical for a rental operation, but they’ re not AI, and they’ ve been around for years.

What AI changes is the intelligence layer: the ability to identify patterns across thousands of transactions, flag anomalies, model demand and personalize customer communication in ways that would be impossible to do manually at scale. For a rental operator managing a mixed fleet across a full season, this capability is more than a nice-to-have; it’ s necessary. It’ s the difference between reacting to the season and shaping it.

For a rental operator managing a mixed fleet across a full season, this capability is more than a nice-tohave; it ' s a necessary.

The Operators Who Figure This Out First Will Be Hard to Catch

Customer expectations in outdoor recreation are being set by industries with much larger technology budgets. Guests booking hotels or private homes, flights and restaurant reservations with frictionless experiences are bringing those same expectations when booking boat rentals, kayak tours and fishing charters.

Operators who can meet these expectations and use the booking data to get smarter are building something competitors can’ t easily replicate: a compounding understanding of their own customers.

Retention is where this becomes tangible for the operator. Repeat customers book earlier, spend more and refer others at higher rates. And they become loyal because their experience was personal, and the follow-ups were tailored to them. That kind of relationship, built systematically across hundreds of customers, is a competitive advantage.

Operators who can meet these expectations and use the booking data to get smarter are building something competitors can’ t easily replicate: a compounding understanding of their own customers.

What the Next Few Years Look Like

The rental operators who will be best positioned five years from now are the ones investing now in systems that learn and get smarter with every transaction, rather than simply recording it. This technology exists today and is accessible to independent operators, not just large companies.

The question isn’ t whether data-driven operations will become the standard in this industry. It’ s which operators will have built that foundation before it becomes obvious to everyone that they should have.

Michelle Faul is chief marketing officer of Digital Sportsman, a U. S.-based technology company and one of the fastest-growing rental management and booking platforms built specifically for outdoor businesses. Find more information at www. dspro. guide.

20 april 2026 www. boatingindustry. com