Meet the Woman Behind the Summit...

Jenn Boyles

Former Airbnb Superhost. Marketing rebel. Direct booking advocate.

I didn’t plan to end up here… running a global online summit, helping STR pros grow their bookings, and teaching marketing like it’s a superpower. But looking back, it kinda all makes sense.

Born into Hospitality

You could say hospitality runs in my blood. My dad was a hotel GM in downtown Vancouver, long hours, long commutes, and a perpetually soaked umbrella. Growing up, hospitality was equal parts glamorous and gritty. I could tell you which fork to use at a formal dinner and how messy a guest room can get when you’re restocking the minibar at 7 a.m.

I loved the sparkle, but I didn’t want to spend my days in someone else’s system. So I went my own way… into design, into marketing and eventually, into short-term rentals.

The Chalet That Changed Everything

After years living in London and then mainland Europe, my now-husband and I turned our ski-side apartment into a wildly successful rental. So we bought a chalet in Austria and went full-on OTA. Airbnb… we drank the Kool-Aid.

But the bookings weren’t what we expected. 

Competition was fierce. Then the phone rang.

A guest who’d stayed under the previous owners wanted to come back. That one call flipped a switch: Direct bookings weren’t just possible… they were better.

We leaned in, tapped my marketing skills, and turned our rental into a fully branded business. More control, more profit, fewer fees, better guests. 

In 2020, when I launched my next vacation rental brand in a new country and opened with 80% direct bookings, I knew I had to help others do the same.

Why I Created the Summit

In 2021, as the world started opening back up, I noticed a major gap…

There were plenty of flashy in-person events popping up again, but what about those of us who couldn’t travel or didn’t have thousands to spend on tickets, flights, and hotel rooms?

So I built something different.

The Direct Booking Success Summit was created as a virtual space for vacation rental pros to learn, connect, and implement… without the cost, the gatekeeping, or the stress.

And I built it with women first.

Because although so many short-term rental owners and managers are women, we still see too many panels, workshops, and lineups led by men. I’m on a mission to help right that imbalance and create a space where women’s expertise is amplified and celebrated.

Now in its fifth year, the Summit is a global gathering place for STR pros who want to grow their business on their own terms and see themselves represented on every stage.

What I’m Doing Now

I’m back in Canada, running Direct Booking Success, hosting the Direct Booking Success Podcast, and speaking at STR conferences around the world. I also launched Book Direct Pro, the first all-in-one marketing platform built for vacation rental pros by a vacation rental pro.

And every day, I wake up excited to help property managers like you build businesses with more profit, more confidence, and more direct bookings.

Want to connect or learn more? Send me an email and let’s chat.

This is your time… let’s build a business that works for you.