Robert J. Pillow

Equity Partner & Online Marketing Strategy Advisor at Caddy Time

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Robert J. Pillow Equity - Partner & Online Marketing Strategy Advisor at Caddy Time

Equity Partner & Online Marketing Strategy Advisor at Caddy Time

With 27 years of experience in full-stack web development and a deep focus on SEO and technical strategy, I bring both performance and precision to the table. My work goes beyond building websites—I'm driven by the data, user behavior, and competitive landscapes that power real results.

Before becoming the guy behind the screen, I was the guy on the greens. I grew up playing golf across Central Virginia and Southern California and served as an Assistant Pro at Oakwood Country Club from 1992 to 1994. That early immersion in the game still shapes how I think today—especially when it comes to discipline, course management, and anticipating the next move.

At Caddy Time, I'm here to help the brand scale with purpose—shaping strategy, overseeing online performance, and making sure everything we do resonates with golfers and caddies alike. From UX and content to speed optimization and digital reach, I build systems that perform like a 3-wood off the tee: fast, consistent, and on target.

When I’m not strategizing or shipping updates, you'll likely find me playing golf, floating near the water, or just kicking back with my two dogs—Biscuit and Gravy.

What People Are Saying

What Makes Us Different

  • On-Demand Talent

    Access a network of vetted, reliable caddies with just a few taps.

  • Frictionless Experience

    For golfers, caddies, and courses — our UX works for all users, not just one.

  • Zero Overhead for Courses

    Courses offer full-service caddie programs without hiring, training, or managing.

Recent News & Announcements

Stay up-to-date with what's happening at Caddy Time.

Greg Norman partners with Caddy Time
Greg Norman Joins Caddy Time

“Partnering with Caddy Time isn’t just about business; it’s about my passion for golf, innovation, legacy, and moving the game forward. I’ve dedicated my career to pushing boundaries both on and off the golf course.”

GolfPairs and Caddy Time partnership
New Partnership with GolfPairs.com

We’re thrilled to announce a new partnership between golfpairs.com and Caddy Time, bringing together the ultimate golfing experience with the most advanced caddy-on-demand platform.

Caddie assisting golfer on course
What Caddies Do for the Game of Golf

A caddie is so meaningful to golf! Not just the round of golf that the caddie works, but the sport of golf—the complete industry of golf. Everything related to golf! Rising tide floats all boats! Nothing is more true than when you take a qualified caddie on a golf round.