Our Team

Get to know Matthew, the founder and operator behind Highmark.

When did you start Highmark?
I started Highmark in 2013. My dad told me he wasn’t going to buy me a truck, so I needed to make my own money. He let me borrow his push mower and weed whacker to get started, and I’ve been working to grow the company year after year ever since.

What is your favorite part of the job?
My favorite part of the job is helping my team members grow their life skills—from learning how to back up a trailer to operating equipment and successfully executing large projects. I also really enjoy serving and supporting members of our community.

What do you like to do in your free time?
I enjoy spending as much time outdoors as possible. In the summer, I like hiking, biking, camping, and exploring the great state of Alaska. In the winter, I’m an avid snowmachiner and fat biker. I love snow!!

Anywhere you’d like to travel?
I’d love to travel to Norway, Sweden, and Finland to see their snow removal equipment and explore those areas. Beyond that, I’d like to continue exploring more of Europe, and Iceland.

Anything else you’d like to share?
I’ve really enjoyed my journey so far with everyone who has been part of the Highmark team over the years, and I’m excited to continue expanding the company and meeting new people along the way!

Get to know Jedi, the Shop Manager at Highmark.

When did you start working at Highmark?
2016

What is your favorite part of the job?
Working along side my buddy that hired me on as his first employee back in high school. Also love to watch the company continue to grow.

What do you like to do in your free time?
I enjoy auto photography, building cool trucks, fishing and reef aquariums.

Anywhere you would like to travel to?
I really want to go to Australia to snorkel/ dive on the GBR.

Anything else you would like to share?
I work at Enstar Natural Gas during the summers; and my years of winter snow work are slowly coming to a close. I really appreciate the clients that take the time to smile, wave, or even come chat with me on snowblowing days. Y’all make long snow days more enjoyable throughout the winters.

Get to know Sydney our Office Manager at Highmark.

When did you start working at Highmark?
August 2024

What is your favorite part of the job?
My favorite part of the job is learning new skills that expand my abilities and communicating with our clients.

What do you like to do in your free time?
In my free time, I enjoy reading, playing with my dog Oakley, and spending time with my family and friends.

Anywhere would you like to travel to?
I would love to travel to Hawaii.

Get to know Jarett who provides Operations Support at Highmark.

When did you start working at Highmark?
June of 2025

What is your favorite part of the job?
My favorite part of the job is being able to work outside all year, along with working throughout the south side of Anchorage and seeing all the views and wildlife

What do you like to do in your free time?
In my free time, I enjoy hunting and fishing.

Anywhere would you like to travel to?
I would like to travel to Ireland.

Get to know DeeDee who is a part of our Project & Snow Team at Highmark.

When did you start working at Highmark?
2024

What is your favorite part of the job?
My favorite part of the job is working on projects.

What do you like to do in your free time?
In my free time, I enjoy hiking, working out, and spending time with my puppy and friends.

Anywhere would you like to travel to?
I would like to travel to Iceland.

Anything else you would like to share?
Do it, lady.

Get to know Dylan who is part of our Lawn & Snow Team at Highmark.

When did you start working at Highmark?
May 29, 2025

What is your favorite part of the job?
My favorite part of the job is running lawnmowers during the summers, as there is something cathartic about seeing the lawns finished at the end.

What do you like to do in your free time?
In my free time, I like to write, as well as take part in all the outdoor activities that people here enjoy.

Anywhere would you like to travel to?
I would like to travel more throughout Alaska.

Get to know Sean who is part of our Lawn & Snow Team at Highmark.

When did you start working at Highmark?
Mid-late August 2025

What is your favorite part of the job?
My favorite part of the job is the friendships I’ve made.

What do you like to do in your free time?
In my free time, I enjoy driving and hiking.

Anywhere would you like to travel to?
I would like to travel to Dubai.

Anything else you would like to share?
It’s a great job to be a part of.

Get to know Seth who is part of our Project Team at Highmark.

When did you start working at Highmark?
2025

What is your favorite part of the job?
My favorite part of the job is getting to operate the loaders.

What do you like to do in your free time?
In my free time, I enjoy snowmachining.

Anywhere would you like to travel to?
I would like to travel to Europe again.

Get to know Oakley who is part of  the Highmark team.

Oakley is our shop dog and Emotional Support Specialist, always nearby to keep morale up. He brings a steady, calm presence to the team and never misses a chance to check in or tag along.