James Kaikis — Co-Founder
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.
Stackforce AI infers this person is a SaaS expert with a strong focus on customer experience and go-to-market strategies.
Location: Chicago, Illinois, United States
Experience: 16 yrs 4 mos
Skills
- Customer Experience
- Go-to-market Strategy
Career Highlights
- Founded PreSales Collective, a community of 35,000+ members.
- Led innovative software evaluation at TestBox.
- Expert in transforming customer experiences across industries.
Work Experience
SolutionExec
Co-Founder (4 mos)
Pavilion
CRO Functional Leader (11 mos)
TestBox
Chief Revenue & Experience Officer (CRXO) (7 mos)
Head of Go-To-Market / Chief Solutions Officer (1 yr 3 mos)
Stage 2 Capital
Limited Partner, Stage 2 Capital Catalyst (4 yrs 2 mos)
GTMfund
Limited Partner (4 yrs 6 mos)
Sylva
General Manager (Post PSC Acquisition) (1 yr 7 mos)
PreSales Academy
Co-Founder (Acquired, Nov 2021) (1 yr 11 mos)
Salesforce
Director, Solutions Engineering (0 mo)
Senior Manager, Solutions Engineering (1 yr 3 mos)
PreSales Collective
Host: The PreSales Podcast (Acquired, Nov 2021) (3 yrs)
Co-Founder (Acquired, Nov 2021) (3 yrs 5 mos)
GTMshift
Founder (7 yrs 4 mos)
Showpad
Director of Solution Engineering, Americas (1 yr 4 mos)
Manager of Sales Engineering (2 yrs 4 mos)
Sales Engineer / Professional Services Consultant (3 mos)
Revinate
Customer Engagement Manager, Professional Services (1 yr 2 mos)
Grand Hyatt San Francisco
Front Office Manager (7 mos)
Hyatt Regency Waikiki Beach Resort & Spa
V.I.P. Manager (1 yr 5 mos)
University of Nevada-Las Vegas
Director of Operations, Student Recreation and Wellness Center (Graduate Assistant) (1 yr 1 mo)
Ohio University
Director of Club Sports (Graduate Assistant) (10 mos)
University of California, Los Angeles
Club Sports Intern (3 mos)
University of Nevada-Las Vegas
Sports Writer, The Rebel Yell (9 mos)
Education
Master of Business Administration (M.B.A.) at University of Nevada-Las Vegas
Master’s Degree at Ohio University
Bachelor’s Degree at University of Nevada-Las Vegas
