Announcing Frontdesk’s New CEO

Frontdesk Co-founder Kyle Weatherly transitions to Board Director, with Jesse DePinto becoming the new CEO of Frontdesk

By: Kyle Weatherly
Co-Founder, Frontdesk

Almost six years ago, on a cold December day in Milwaukee, Wisconsin, my wife, Ruthie, and I had just returned from spending a year overseas. We may have been tourists, but we weren’t living like tourists.

After that trip and spending a year jumping from country to country, vacation rental to vacation rental, I felt that consumer travel would soon change forever. The opportunity to redefine hospitality for a new generation of travelers was clear.

After a few conversations with Jesse, a former technology vendor at my first company, we launched Frontdesk with a single unit as a short-term rental in our hometown and immediately started booking. In January. In Milwaukee. We knew we were on to something.

February 28, 2017 — Frontdesk hosted their first guest, in their first unit in Milwaukee, Wisconsin.

So, Jesse and I sat down and wrote a mission statement that included lines that we still live by today. We aspired to build something meaningful. A business that could generate opportunities for many. A culture that inspires, one that aims to put team success above individual success. To “Clean the toilets” or whatever it takes for the team to succeed. We began reaching out to landlords in city centers and offering a service for managing their flexible stays in an efficient and scalable way, enabled by our technology, and our desire to serve.   

With a focus on systematizing processes, wowing the guests, and hospitality, we figured we could take this idea and build something big together. From there, we started to grow. People liked the idea, our team started growing, and with sweat and sacrifice, a new, customer-obsessed hospitality company was born. And today, that company has grown to over 30 U.S. markets with more than 1000 units across 150+ buildings and counting.

August 2022 — Frontdesk’s newest units in Birmingham, Alabama, and Cleveland, Ohio.

Since those early days, Frontdesk has served over 400,000 guests and earned an average satisfaction rating of 4.7 out of 5.0. Even through a pandemic, Frontdesk remained strong, growing while others could not and striving to continue with a mission of getting our hands dirty while helping travelers enjoy cities the way locals do. Due to good fortune, financial discipline, and intense efforts from our entire team, our company has never been in a stronger position even in these most challenging times.

In our earliest conversations, Jesse and I had always planned for him to eventually lead and take the company to the next level. Over the last 5+ years, we have worked tirelessly to land in 30+ markets and grew to 1000+ units. Now for the next five years, we get to execute on the fun part, expanding within our current markets and building a residential hospitality brand in the process.

September 2022 — Frontdesk embraces remote culture with 300+ employees scattered across the country.

Jesse has been leading the day-to-day operations for some time, so, more than anything, this is simply our job titles catching up with reality. Today is an exciting inflection point in the company’s history, and Jesse’s arrival into the CEO role marks a turning point that we are entering a new phase of growth for the company.

It has been an honor to lead Frontdesk, and I am thrilled that the board has unanimously appointed Jesse as the next CEO. I believe Jesse will fully realize the vision we have laid out over these past five-plus years and make Frontdesk the most beloved hospitality brand of this generation.

Yours truly,
Kyle Weatherly