Meet Jill

Explorer. Nomad.
Cross-Country Moto Rider.
Proud WordPress Geek and
Business Tech Strategy Nerd.

{Just, please, don’t call her a “guru” –
that’s a silly title!}

Digital Nomad Traveling the USA

3395 Days and counting so far.

2 wheels. 6 wheels. 250cc. 750cc. 400hp. Human pedal and paddle power.

Home is simply where we park it.


WordPress Forensic Anthropologist

Solving WordPress headaches one site at a time by digging deep and finding the right solutions quickly and efficiently. At Ultimate WP Help, we design and develop WP sites for fabulous clients and help with tasks big and tiny all along the way. And yes, Jill actually is an anthropologist!

Ultimate WP Help: We’re the Systems and Operations team that takes all that overwhelm off your hands so you can focus on your genius. It’s like having a Fractional CTO and team on retainer and clients love it!

Rolling Through It

Jill doesn’t share so that you should want to live HER life, but so that you should more passionately want to live your own.

Forthcoming inspiration in the book:
Rolling Through It: Travel As A Cure For Chaos of the Mind. 

So when are YOU going to start living out your dreams?

Get Updates

About The Photo

Jill Sessa Nomad Fractional CTOWater fuels Jill’s adventures. Summer into Fall of 2021, Maui opened up to travelers and Jill couldn’t resist. The Aloha spirit is magical and everything this world needs right now.

Embrace the every day, no matter where you find yourself!

Thank you for today! I’m freaking giddy with excitement! It’s been a long time since I’ve felt this empowered and excited to launch something without having to settle for something to be “ugly” or not work quite the way I want it to. I’m seriously in heaven.

Angella Johnson

Business Visionary, Marketing and Messaging Strategist, Soul Vision Strategies

About The Photo

The Cadillac Ranch, outside of Amarillo, TX is a famous Route 66 stop. But few people know that just 20 miles away, a similar work was installed using VW Beatles. The Love Bugs!

Taken on Jill’s mother’s birthday, this photo also shows Purl, the tiny dog who was Jill’s constant companion until her untimely death on Aug 10, 2013.

2013-07-12 11.34.39

Can’t tell you how great it is to work with you.  Its been a huge weight off me these last few weeks having you look after everything so well.  It is very much appreciated.

Tim Orr

#1 Eagle Rider Booking Agent, The Lost Adventure

This is the best feedback we have had on any presentation in the 5 years we’ve been doing these events.

People are absolutely loving it and you were on fire!

Event Organizer, 400+ in attendance


Jill is by her very nature a helper and naturally gifted teacher. Don’t let the moving all about the country thing fool you, she is right where she needs to be when her clients are seeking help with {WHAT} they are doing with their digital world.

Easiest way to get started is by scheduling a complimentary site review where Jill can look at your website (or hopes for one!) while you chat together about {WHAT} is bugging you. Then sign up for an annual Ultimate WP Help membership, which grants you access to the geniuses of UWP.

{WHAT} are you waiting for?


Moving about the country and the world, truly on a day-to-day basis, can make it hard to keep up with her, just ask Jill’s family. Jill used to blog about her adventures living full-time on the road in a tiny motorhome, with two tiny dogs, a tiny fold-up bike and a sorta tiny Vespa 250cc. Now she is more likely to only take the time to post some amateur photos on Insta or FB. Catch {WHERE} she is on Facebook or Instagram.

Jill has returned to her formal speaking gigs, and will certainly consider a visit with your riding club, adventurers’ group, small business forum or even meet you at your favorite bar (coffee or cocktail!) if she is in your area or plans to be. Bigger engagements? Please ask for a proposal. Read more about topics and bio here.

Why don’t you send her a message and see if you can intersect some{WHERE} near you? Her day to day life is an inspiration to many and makes for a fun conversation.


The journey and route is planned only minimally, taking weather, friends and serendipity into account.

But as for {WHEN} you can see Jill or {WHEN} the book is coming out, we’ll let you know in the newsletter, so get yourself signed up.

As for the most important {WHEN} … when are you going to get your own life amped up to living full out? You just have to take the first step. Jill may seem like she is inaccessible and always on the move, but that doesn’t mean she won’t make time to chat with you… in fact, she welcomes the chance to get you rolling.


Ok, you’re one of those peeps that needs the more formal bio.

No problem.

Get the surprising back-story and inspirational life-story on the bio page.

Jill Sessa Rides a Vespa


Sort of an existential question, but you probably want to know {HOW} you can chat, meet or work with Jill, otherwise you wouldn’t be here, right? Start at the How Can Jill Help You form and we’ll go from there. Deal?

Oh Hey! Make Sure To Get The Latest Updates

About The Photo

Jill lived on the road full-time for 18 months in a tiny RV called Ms Piggy, due to shape, size and gas mileage! This was from the first month with both Ms Piggy and Jerome. Guest appearance by one of 17 pairs of glasses along for the journey.

Logan joined the tiny family several months later.2014-02-08 08.46.49


It is now just Logan, Jill, a 2004 Sprinter named the Flying Tomato, a 1971 Honda Trail 90 and lots of various outdoor toys. The only constant in our life is change!