Looking Back & Moving Forward: Celebrating 20 Years of Upsellit

Kristen IndiharAwards

Look Back & Moving Forward: Celebrating 20 Years of Upsellit

October will be a special month for Upsellit as we will be celebrating our 20th anniversary. From humble beginnings to industry-leading innovations, we’re thrilled to celebrate this incredible journey.

Our 20th year is all about reflecting on how far we’ve come and what’s next for Upsellit. It’s a time to celebrate our achievements, our growth, and the partners who have helped us get to where we are today.

Anniversary Celebration in Cancun

In celebration of our 20th anniversary, we’re launching a year-long celebration, starting with an unforgettable company retreat in Cancun next week! We’re looking forward to coming together, enjoying some well-deserved relaxation, and strategizing for the future. Stay tuned for updates on our retreat and other exciting announcements throughout the year. 

Upsellit’s Journey Through the Years: Key Milestones

Founded in October 2005, Upsellit began as a privately owned business and remains so to this day, driven by a vision to revolutionize ecommerce. We began by launching SmartAgent™, the first-ever Sales Chat Bot, a tool capable of answering FAQs while upselling products and services — a game changer for online retailers. Not long after, we pioneered the industry’s first exit detection technology, allowing online retailers to engage shoppers at the exact moment of site abandonment. 

By Spring 2006, Upsellit reached profitability and began to make waves in the industry. Our commitment to innovation and our ability to quickly pivot to market demands allowed us to continuously evolve. 

As we hit our 20th anniversary, we’re incredibly proud of how far we’ve come. Our journey has been marked by continuous innovation, a commitment to excellence, and, most importantly, our people. We’ve built a team that’s passionate about helping ecommerce businesses grow, and we’re more excited than ever for what lies ahead.

In Conversation with Chris Wampler: The Innovator Behind Upsellit

To mark our 20th anniversary, we sat down with Chris Wampler, CEO, co-founder of Upsellit, and system architect to get his perspective on the company’s journey, key moments, and future.

Q: Can you take me back to Upsellit’s early days? How did it all come together? What was the original vision, and who was your first client?

Chris: “In 2003 I turned down several better offers to take a job at a company that staffed chat agents for various businesses under the promise that I’d be able to integrate one of my passions into their products: Artificial Intelligence chat. The goal wasn’t to replace people but rather to supplement the easy parts so one agent could handle dozens of chats at once rather than just two or three.

A change in leadership in that company led to that project being scrapped so I decided to go out on my own. Upsellit originally had a very different business model than what we do now. Essentially, we were artificial intelligent chat agents that sold products on the receipt pages of ecommerce sites. True up-sells.

Our very first client sold diet patches and I still remember the night we made our first post-transaction upsell (I believe it was for a service that offered discount hotels). Our bounty was $10 and to celebrate I took my friends out to a bar and spent $150. I guess that was the only time Upsellit was ever in the red.”

Q: Upsellit started as a post-transaction upsell tool—how did the shift to abandonment recovery happen? What sparked that change?

Chris: “While I’m a software developer and we are a tech company, at the end of the day it’s the sales team to whom we answer. Upsellit’s biggest strength is our ability to listen to the market, pivot, react and quickly bring to market products as we detect niches. I’m proud to say that out of the thousands of times I’ve heard a question starting with “Could we build…” my yes answer rate has been close to 99%.

There have been misses as well, and we’ve had to let products go, but in the end the simplicity of abandonment recovery has always been a major draw for online businesses.” 

Q: Over the years, Upsellit has grown and evolved. What was the key moment that really changed the company’s direction?

Chris: “The biggest shift I noticed is when a large portion of our business started coming from contacts that left their roles and brought us on at their new companies. This is when I realized that we had proved our value and offered good enough service that people were willing to stake their reputation at their new companies to bring us aboard. That’s a huge compliment to both our technology and support and sales team.” 

Q: In the last 20 years, ecommerce has transformed a lot. What’s the biggest shift you’ve seen, and how has Upsellit adapted?

When we first started, ecommerce sites were the unloved stepchild of major brands. Many huge name-brands outsourced their brand identity to 3rd parties who put up websites that were little better than GeoCity sites. (Shout out to anyone old enough to know GeoCities). Under this environment pretty much anything was allowed as long as it worked in the newest browser: Internet Explorer 6. It wasn’t uncommon for a brand to say “Oh yeah, our site was down on Sunday. Oops.” It was an easy ecosystem for us and our competitors to exist in.

Since then the internet business for many businesses has usurped their brick and mortar revenue. Reactive sites delivered at lightning speed with 99.999% uptime and the most seamless and modern of user experiences has become the bare minimum even the smallest of brands expect. Polished design and functionality is a must, and our technologies are extremely front-facing so we are a large part of this.

Over the years we’ve seen competitor after competitor drop off because they are unable to exist in this type of environment. Upsellit, on the other hand, has thrived. Our technologies, attention to detail, designs and speed of implementation have allowed us to satisfy even the most persnickety clients. Just as a third party technology SaaS vendor we enter the relationship on strike two, and more often than not we win over even the most hard-nosed of contacts with our professionalism and processes. 

Looking Ahead: The Next 20 Years

As we celebrate 20 years of innovation and success, Upsellit is committed to continuing to push boundaries and bring new ideas to market. With upcoming launches like Shopify CRO Analytics and more groundbreaking innovations on the horizon, we’re excited to help ecommerce businesses grow and thrive for the next two decades and beyond.

Here’s to 20 years of success, and to the future of Upsellit — we can’t wait to see where the next 20 years will take us!

Want to join us on this exciting next chapter? Reach out to learn how Upsellit can help your business grow.