We learned at a young age that if you want something done right, do it yourself. So we did.
Which Side Digital is an all-in-one digital marketing co-op that came out of a couple upstart marketing and design professionals asking themselves: “Why not?”
Partners
Creative Director
Colton Colglazier is a Founding Partner and the Creative Director of WSD. With over a decade of professional design experience, he leads creative operations with energy — from engaging web & ad experiences to standout brand identities.
Fun fact: He twice creative directed the best performing digital ad campaigns in the DCCC for the 2022 and 2024 cycle!
But that’s not all. Colton has conquered more than just the design world! From running with the bulls in Pamplona, to lacing up hiking boots to journey the Appalachian Trail. When not setting trends in design, he can be found hiking or woodworking.
In short, he blends art, adventure, and a dash of humor to bring fresh, unforgettable ideas to life!
Comms Director
Team
Senior Design Strategist
Kayla is a Senior Design Strategist at Which Side.
When Kayla isn’t drawing or designing, she’s most likely in the woods with her dog, Sage! That’s where she finds her focus, it gives her ideas room to breathe. She strives to bring intentional energy to every project she works on. With each design her goal is to create visuals that are authentic, grounded, and genuinely tell your story.
Senior UX/UI Designer
Jenna Becker is a Senior UX/UI Designer at Which Side with over 4 years of experience in UX design. She holds a master’s degree in User Experience Design from Arizona State University.
Jenna has a passion for creating user-centered web designs and has worked on countless websites for WSD. Outside of work, Jenna enjoys gaming, reading, and spending time with her cat Nashor.
Senior Digital Content Manager
Social Media Manager
Jamie Coffey is a Social Media Manager and Operations Assistant with Which Side Digital. She has worked in Social Media Management for over 4 years. She has experience in social media strategy and execution, ranging from small businesses to high-profile content creators. She holds a BFA from Marymount Manhattan College.
She lived in New York City for over 5 years where she specialized in producing, fundraising, and spearheading social media outreach for grass root events in theatre, film, and art. She is very comfortable jumping between creative, collaborative and administrative spaces — utilizing her words to paint to both stories and engaging rhetoric where ever she goes.
When she’s not online, she enjoys shooting film photography of the great American landscapes as well small city sidewalks.
Social Media Manager
Chris Cardona is a Social Media Manager with Which Side Digital. He holds a EdM in Education Studies from SUNY University at Buffalo and is completing his MA in Political Psychology from SUNY Stony Brook University by Summer of 2026.
Chris looks to bring his passion for politics and its intersection into our everyday lives with his background in education, focusing on intentional social media communication in an ever online world. When he’s not keeping up with what’s going on in politics, you can find Chris reading a history book or playing a videogame (with his cat Murphy close by).
Digital Content Manager
Margaret Merritt is a Digital Content Manager with a background in professional writing and editing, as well as over 10 years of political work focusing on community and outreach. She graduated from St. John’s College with a double major in the History of Philosophy and Mathematics.
Her focus is writing excellent content, from emails to video scripts to blog posts, that showcase the client’s message and speak to the moment. In her downtime, she’s reading, engaging in fiber arts, cooking fun dishes, or walking on an abandoned railroad track.
Design Consultant
Rosalyn Stuart is a Designer & Consultant at Which Side.
From humble beginnings working on the ground on startup campaigns in Illinois, our team set out with a goal of delivering game-changing work to disrupt the political space. We quickly grew as a result of our efforts and landed in Alaska, where we helped an underdog candidate flip the state’s House of Representatives seat for the first time in nearly 50 years.
Our intitial successess have driven us to push the envelope on every project we find ourselves a part of. We got into the political world out of a want to make real change in people’s lives, and we’ve successfully done just that. We’ve worked to create a better experience for our clients than they’re used to in the space, all while catching the eyes of every person who comes across out work.
Now, Which Side enters its third year of bolstering campaigns, businesses, and everything in between with bold design, strategic messaging, and a fresh approach. We take pride in seeing our clients succeed and are always thrilled to watch them soar to new heights.
Our story doesn’t end here, but enough about us – this is where your story begins.
Book a free meeting today to discover where our partnership can take you.
2022
Which Side Digital Founded
2022
Junaid Ahmed Campaign
WSD worked with Junaid on advertising, branding, print media, social media, and web design.
2022
Mary Peltola Campaign
WSD worked with Peltola on ad design, digital organizing, print media, social media, and web design.
2022
Spink Landscapers
WSD worked with the Alaska Democrats on branding and social media.
2023
Campaign In A Box
WSD worked with the Alaska Democrats on branding, media, and web design.
2023
Alaska Democrats
WSD worked with the Alaska Democrats on branding, print media, and web design.
2024
Mary Peltola Campaign
WSD worked with the Alaska Democrats on branding, print media, and web design.
2024
Supply Drop Program
WSD Launches Supply Drop Program for Small Campaigns.
2024
Email Fundraising Program
WSD Launches Email Fundraising Program.
2024
Ben Alke Campaign
WSD worked with Ben Alke on fundraising, graphic design, and web design.
2024
Alaska Democrats
WSD worked with the Alaska Democrats 2024 Coordinated Campaign on advertising and voter turnout.
2025
Hawaii Democrats
WSD worked with the Hawaii Democrats on branding and website design.
