CloudFest USA Interview with Jessica Frick

This week’s insider convo is with Jessica Frick, Head of Product at Pressable, a managed WordPress hosting company. Jessica has worked in WordPress-related roles for 15 years, including four years at Liquid Web. Jessica also previously founded and ran a consultancy called Renewabelle, which offered end-to-end project management and execution.

In our fun back-and-forth, you can hear from Jessica on what she views as the biggest evolutions in the WordPress hosting space, why she’s excited about CloudFest USA’s new home and even her favorite David Bowie song! 

Briefly introduce yourself to any members of our readership who may not know you yet!

Hi! I’m Jess Frick, Head of Product at Pressable, a managed WordPress hosting solution that’s owned by Automattic. I’ve spent over two decades in digital commerce and product strategy — and I still geek out over clever infrastructure, meaningful metrics, and building things that actually work. I’m passionate about helping agencies and creators succeed online, and I believe great hosting should be powerful, scalable, and painless.

You’ve been at Pressable for more than three years now. What are some of the biggest changes and developments you’ve seen in the managed WordPress hosting space?

The space has evolved from “fast and secure” being differentiators to table stakes. Today, truly managed WordPress hosting is about unlocking new capabilities — performance at scale, deeper developer integrations, and tighter agency support. At Pressable, we’ve leaned into infrastructure flexibility (thanks to WP Cloud), invested in tools for advanced developers and less technical users alike, and focused heavily on removing friction for growing businesses. It’s no longer about just hosting; it’s about partnerships.

We’ll be announcing your panel very soon (maybe even as soon as next week), but what topic or topics are most front of mind for you in 2025?

In 2025, I’m focused on sustainability in scale — not just in terms of infrastructure or carbon footprint, but in how we build products, support customers, and drive predictable growth for agencies and freelancers. AI is obviously changing workflows, but the real opportunity lies in how we humanize the experience around it. We can automate a lot, but trust, creativity, and collaboration still have to come from us.

What are you most looking forward to about CloudFest USA 2025 and its new home in Miami?

The energy! Miami brings such a vibrant tech-meets-culture vibe, and I can’t wait to see how that fuels the conversations at CloudFest. With the amazing lineup of speakers and attendees expected, I’m genuinely excited to connect, swap stories, and hear what’s actually working for people in the trenches.

If you could program your own fireside chat with one person currently working in the industry, who would it be and why?

Kevin Ohashi. He’s the mastermind behind Review Signal and one of the most honest voices in the hosting space — which, let’s be real, is not always known for transparency. I’d love to talk with him about performance benchmarking that actually matters, what most hosting companies get wrong in their messaging, and how customers can cut through the marketing fluff to find real value. Plus, I’d 100% ask what still surprises him when he runs those massive performance tests — and whether there’s a polite way to say “this stack is garbage.” He probably knows.

If you could program your own fireside chat with any person, dead or alive, who isn’t currently in the industry, who would it be and why?

David Bowie. Still Bowie. Always Bowie. He was a master of shipping bold ideas with purpose — just with fewer meetings and far more sequins. I’d want to know how he balanced innovation with usability — how he knew when to take a wild swing and when to refine what was already working. I’d ask how he built for a future his audience couldn’t yet articulate, and how he stayed confident in his vision even when the early feedback sounded like, “Wait… what is this?” If we’re not channeling Bowie energy into our release cycles, we’re leaving magic on the table.

Last but (certainly) not least… what is your favorite Bowie song?

Oh gosh… that’s a hard question! It depends on the day. 

I’d have to go with “Heroes,” which I love so much, my husband and I walked back down the aisle to it after we were married. 🙂