The Future of Club Management

Table of Contents

• CourtReserve and the Catalyst Tour

• Our Day 1 Host: Rally House Pickleball Club

• DAY 1 Meeting at Rally House

  • Location: Upstairs conference Room at Rally House …

• Some of the Participants

• DAY 2 Meeting at the Sheraton

  • Location: Conference Room, Sheraton La Jolla, Cali …

• My Take

CourtReserve and the Catalyst Tour

I had been wanting to check out the CourtReserve Catalyst Tour for quite a while. Designed as a regional user group gathering for CR’s 2,400-strong client base in North America, the tour recently stopped in La Jolla—about 128 miles south of my office—so I jumped at the chance to join.

The CR website promises “Uncover new ways to elevate your operations with our deep dives, best practices, and hands-on sessions-and be the first to glimpse our 2026 Product Roadmap” and they didn’t disappoint. It was a high-energy event led by an exceptional group of people.

Ever since 2020—back when the company had only 20 or so employees—I’ve been writing about CR’s stellar team and their unparalleled customer support. Today, CR has grown to around 80 employees, and the staff members I met in San Diego proved that quality hasn't suffered with growth. They are, without exception, absolute gems.

Education Manager Chloe Ludder, the moderator, knows every aspect of CR’s vast number of functionalities, which enabled her to answer most of the questions asked. Ashley Owen was close by to jump in and elaborate from a company owner point of view. Josh Sinke, Customer Support Team Lead, jumped in when needed and also presented. So did Josh Willey, Product Manager - Integrations, whom many of our readers know from CR webinars.

Our Day 1 Host: Rally House Pickleball Club

Location: Rally House Pickleball Club, Carlsbad

Just across the street from Palomar Airport, where I worked in Aerial Photography for a bunch of years in the ‘90s, Rally House is a marvellous example of a well-planned, well-run, and very busy Pickleball facility.

Rally House owners Sara and Nick Dawson (no relation to Steve Dawson at Bobby Riggs Racket & Paddle further down south in Encinitas) were gracious hosts and engaged participants in the meeting.

The facility has 11 premium indoor courts and features game recordings with instant replay sent to a player’s mobile device. Plus: Pro shop, wellness center, courtside lounges, and snack shop.

DAY 1 Meeting at Rally House

Location: Upstairs conference Room at Rally House Pickleball Club, Carlsbad

CourtReserve (CR) users from the San Diego area, Wisconsin, and Illinois had signed up for this event. Expertly organized and moderated by CR’s Education Manager, Chloe Ludden, the conference room of Rally House Pickleball Club in Carlsbad (San Diego North County) was well-suited for this size of group.

Driven by Chloe Ludden’s confident leadership and expertise, the room felt warm, collaborative, and engaged. Holding an MS in Human Development from Syracuse and a BA in Psychology from UConn, Chloe is uniquely equipped to represent CR—guiding attendees to truly collaborate, listen, and extract maximum value from the training event.

Chloe and CR Co-founder Ashley Owens explained the CR Club Growth Flywheel, the “Framework for running and growing a racquet sports club.” CourtReserve Club Growth Flywheel is “a five-pillar operational framework designed for tennis, pickleball, and padel clubs to compound small wins, reduce admin friction, and scale sustainable facility growth.”

Throughout the session, Chloe introduced key topics and invited the room to weigh in—starting with Events. The ideas participants shared were well worth taking note of, including:

• Turn members into Ambassadors to run events like Ladders for the club.

• Weekly Kids Camps in summer at Rally House Pickleball added 80 new family memberships to the club.

• Date night for couples, combined with programs to take care of their kids.

• Progressive Intro Hours for beginners, “stay on for more play and learn.”

• The University of Wisconsin has 2,500 students who play Pickleball.

Meanwhile, Ashley Owens listened and asked clarifying questions when participants suggested ways to improve CourtReserve.

Other topics included “Dead Time” programming, Stripe of SafeSave, cancellation periods for events, add-on revenues, and sponsorships. Interestingly, Ashley shared that her club Old Coast Pickleball in St. Augustine, Florida, charges $4,500 a year for court sponsors, and $2,000 a year for water fountain sponsors.

Some of the Participants

DAY 2 Meeting at the Sheraton

Location: Conference Room, Sheraton La Jolla, California

Chloe opened the session covering Financials, Package Sales, and Reporting. I found the segment on the Audit Log, presented by Josh Willey, particularly compelling. The log gives admins complete visibility into who generated specific reports and when—allowing management to verify access permissions and act accordingly. Josh also highlighted the End-of-Day Report and the Aged Fees Report, which tracks outstanding payments.

We also learned about

• Promo Codes are released to all customers and can be used in Patch, too.

• Public Bookings (Easily book a reservation without having an account.)

• PULSE, a snapshot of a user’s facility, refreshed daily at 2 am.

• Booking Heatmap (Hourly bookings by day of week.)

• An AI Bot named Rally

My Take