About Us

Hi! We're Matt and Stefanie and together (with an amazing team), we're Trailguide Digital.

It all started when one biomedical engineer with a marketing focused MBA (Matt) and one communications professional (Stefanie) decided they were sick of working for other people and took the risk to start working for themselves. 

That feels important to point out – we are small business owners (and parents!) and we understand the sacrifices entrepreneurs like you make to start and scale your business. Not to mention the worry, the sleepless nights, and the nagging thoughts of ‘am I crazy?’ and ‘did I do the right thing?’. 

We also know how easily the joy of pursuing your passion and being your own boss can get lost among the details of, well, running a small business. Accounting, hiring, inventory, payroll, IT, a website, social media… the list goes on. Lucky for you, we actually like that stuff! 

And because you might be wondering (a lot of people do and feel awkward asking), yes, we (Stefanie and Matt) are married. Alongside running Trailguide, we’re wrangling (or at least trying to…) three boys, a hyper border collie, and a (thankfully) calm spaniel. 

When you work with us, you are working with a team that understands the value of a work/life balance and how hard that is to find and maintain as an entrepreneur. You may be asking yourself ‘how is that possible when I run my own business?!’ We certainly have. Our goal is to help you find that balance while growing your business through the right business technology and more efficient digital marketing.


What’s in a name?


A lot! We get asked ‘why Trailguide’ pretty often. Yes, we do a lot of hiking (because three kids and a crazy dog….) and yes, the idea all started on a backpacking trip.

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. Not just because we love hiking with our kids but because it was often on hikes with friends that we would be asked for business and tech advice.

Ripe with cheesy analogies, Trailguide Digital seemed a fitting (and fun) name for a company dedicated to guiding clients through the digital world, run by two parents who spend an inordinate amount of time out on the trails trying to exhaust their hyper kids and crazy dog.

Meet 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 Digital’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 sales 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.”