James Kaikis

Chief Revenue & Experience Officer (CRXO), TestBox

I’ve always been fascinated by what makes a great customer experience—not just good, but truly memorable. My interest piqued while working in hospitality at Hyatt, where I learned how small details could turn a routine interaction into something special.

That same obsession led me to tech, where I learned to scale exceptional experiences across sales and GTM teams at Showpad and Salesforce.

Then in 2020, I saw an even bigger opportunity—the need for a real community in PreSales. So I built one.

The PreSales Collective started as a simple idea and grew into a global movement with 35,000+ members, four business lines, and a full-time team dedicated to elevating the profession. In 2021, it was acquired, a milestone that cemented just how powerful community can be in shaping an industry.

Now, at TestBox, I’m taking that same passion for innovation and connection and applying it to how businesses evaluate software. The B2B buying experience is broken: endless sales cycles, generic demos, and a lack of real hands-on experience before making a decision. TestBox is changing that by enabling buyers to test-drive software in live, pre-configured environments before they buy, leading to better, faster, and more confident decisions.

We’re redefining the way companies purchase technology, making the process easier, more transparent, and built for today’s fast-moving GTM teams.

Outside of work, you’ll find me traveling, hunting for the best new restaurant, or diving into a new challenge—whether it’s fitness, an unfamiliar experience, or a tough problem that needs solving. I believe the best insights come from staying curious and never getting too comfortable, and that’s how I approach everything I do.