About Us

Thanks for visiting! Let us tell you a little bit about ourselves.

The Trailguide Digital Story


It all started on a hike in 2015. Blame it on a high dose of fresh air and sunshine, but it was in the middle of the Ventana Wilderness that Matt decided to leave his career in the biomedical field and spend his time doing what he loves — working with entrepreneurs to bring their ideas to life and helping small businesses grow. 

Thus, a new business was born. But it didn’t have a name.

Fast forward to Christmas, when Matt was gifted a sketch of him on a hike with two of his sons and the word ‘Trailguide’ came to mind. Ripe with cheesy analogies, Trailguide Digital seemed like the perfect fit for a company dedicated to guiding clients through the digital world and with them, forging a path to success (told you the analogies were plentiful). 

In 2017, Matt’s wife, Stefanie, joined the Trailguide team after leaving a career in the communications field. With three boys, two spaniels, a border collie, and a small business of their own, Matt and Stefanie (really) understand how the right business technologies and well thought out marketing strategies can save your sanity (and free up time for more hiking!).


The Trailguide Team



Matt Gallegly

Matt Gallegly

Owner/Technology Consulting Director

Matt’s nearly 20 years of professional experience includes building highly individualized business systems to increase efficiency, productivity, and sales for a variety of clients ranging from small business start-ups to medical associations with international reach.

With a degree in BioMedical Engineering from Vanderbilt University and an MBA from the UC Davis Graduate School of Management, Matt understands the importance of approaching problems both systematically and creatively. 

This combination of education and work experience allows Matt a unique understanding of the specific technological challenges facing business owners and the skills to develop comprehensive systems and marketing solutions.


Jamie LeMaire

Jamie LeMaire

Photographer/Content Creator

Jamie is Trailguide’s secret to capturing the personality, quality, and value of our clients and their products for web redesigns, social media, and advertising. In a past life, Jamie and Stefanie worked together in the communications department at a local boarding school, Jamie as a graphic designer and Stefanie as a social media manager and content creator. 

A little about Jamie:

“I love anything and everything creative. Making things look beautiful is my passion. Photography, fashion, design, art. 

My two sons are my entire world, and together with my husband, we love to bike ride, go to sporting events, dirt bike riding, and explore along the coast. 

My perfect day consists of watching my kids play baseball, then heading to a winery in sunny Carmel Valley with my girlfriends, followed by a homemade dinner by the fireplace with my family.”




Stefanie Gallegly

Stefanie Gallegly

Owner/Digital Marketing Director

Stefanie Gallegly is Trailguide Technology’s social media and digital marketing expert. She brings years of experience managing the digital presence of organizations in a variety of fields ranging from education to foodservice to luxury retail. Stefanie specializes in social media ads and ad funnel development, social media growth and strategy, email marketing, content creation, and website design.

With a degree in Human and Organizational Development from Vanderbilt University’s Peabody School of Education and as a graduate of the Accelerator program at Vanderbilt University’s Owen Graduate School of Management, Stefanie brings an intellectual and real-world understanding of how business owners can harness the power of relationships built through social media to drive an increase in revenue.


Cait Leinberger

Cait Leinberger

Digital Marketer

Cait is Trailguide’s Jill-of-all-trades, helping with just about everything from email newsletters to custom CSS on websites. She also survives arctic blasts like a champ while we complain about being cold on 50 degree California mornings. 

A little about Cait:

“Hey-o! I’m Cait – a Minneapolis based graphic designer and communications specialist.

I’m a coloring expert and social media guru. I’ve worked in the communication, digital design, and marketing industry for over 8 years. I find inspiration in fresh ideas and staying on top of the changing digital landscape. I love to analyze results, build brands, and create compelling content.

In my free time, I doodle, enjoy traveling with my husband (pilot benefits!), compete in triathlons, volunteer at Feed My Starving Children, and escape to the great outdoors in Minnesota with our two furry children.”