The Making of The Digital Ring

From a bold idea to a thriving agency, our story is all about creativity, collaboration, and a whole lot of laughs. Here’s how it unfolded.

February 2015

Co-founders Matt, Mason, and Nick set out to shake up Madison’s marketing scene by creating a digital-first agency focused on blending creativity and data-driven strategy. And with that, The Digital Ring was born.

The Digital Ring

NOUN

[thuh dij-i-tl ring]
1. A creative collective turning bold strategies into measurable results—powered by curiosity, collaboration, and a little chaos.
‍
2. (Alt.) The ultimate fusion of wit, work, and Wi-Fi.

August 2015

An early win? Partnering with American Advantage-Lindow Insurance, one of our longest-standing clients. Their continued partnership is a testament to the power of long-term collaboration and shared success.

February 2016

Moving into our first spacious office in Middleton opened new opportunities—not just for collaboration, but also for pranks. Matt, Mason, and Nick quickly became the go-to targets.

March 2017

We began our partnership with Church Mutual Insurance Company, the largest insurer of religious organizations in the nation, marking a significant milestone in our growth. Years later, we redesigned Church Mutual’s website—one of our biggest site builds to date.

Fun fact: Over the course of this project, no less than five team members on the account welcomed new babies and adopted pets. #blessed

“If you want a marketing agency that communicates flawlessly, understands the digital landscape, and consistently over-delivers, I highly recommend them.”

Brian Pensinger, Sr. Digital Marketing Specialist at Church Mutual Insurance

October 2018

We were named one of the “Best Places to Work” by Madison Magazine—a title we’ve proudly earned multiple times since. That same year, we brought home ADDYs for creative work and, by 2019, landed on the Inc. 5000 list of fastest-growing private companies in the U.S., ranking #6 in Wisconsin.

See why the crew thinks TDR is a great place to work →

November 2019

We continued to grow and break ground on an office expansion. As luck would have it, the expansion was finished right in time for a global pandemic and stay-at-home orders.

April 2020

With stay-at-home orders in full swing, we embraced remote work with open arms—and picked up a new set of go-to phrases:

“Oops, sorry, I think you froze.”
“Oop, sorry, I think you’re muted.”
“Can everyone who’s not speaking please mute?”
“Can everyone see my screen?” (Shares the wrong tab.)
“Oh, no, you go first.” (Overlapping voices for 10 seconds.)
“We’ll give him one more minute before we get started.”

January 2021

Remote work came with its challenges, but it also brought incredible opportunities. We expanded beyond Wisconsin, welcoming talented team members from states like California, Texas, and Maine.

When the pandemic dust settled, we gave our Madison crew an in-person option by leasing coworking space in The Spark Building downtown—perfect for brainstorming sessions, collaboration, or simply remembering what it’s like to wear real pants to work.

May 2023

This year, we went all in—literally. For our annual team retreat, we swapped Matt and Mason’s lake house for Las Vegas. There, we balanced strategy sessions and bonding with a healthy dose of shenanigans.

October 2023

AI introduced new ways for us to enhance efficiency, creativity, and innovation. To explore its possibilities, we invited the team to use AI to create images that represented TDR. The submissions ranged from hilariously on-brand to totally wacky.

March 2024

Bang the (virtual) gong—this year, we hit an incredible milestone: designing, building, and launching over 500 websites! Recent highlights include work for SHINE Technologies and The Aldo Leopold Foundation.

December 2024

This year, we reached a major milestone: managing over $8.7 million in ad spend across industries and platforms. From impactful display ads to ROI-driven campaigns, we helped our clients achieve their goals in measurable ways.

Today

The Digital Ring has evolved from a bold idea into a thriving agency powered by creativity, collaboration, and a commitment to excellence. Whether brainstorming big ideas, embracing cutting-edge tools like AI, or building relationships as a team, we remain focused on what matters: delivering great work and making an impact.

Here’s to where we’ve been—and the road ahead.

Mason Kemp

TDR Partner

The Digital Ring just transformed into a food of your choosing, what would it be and why?

Stir Fry. Combination of many food groups and flavors. Just like no day is the same at TDR, neither is making stir fry when making it the second or third time.

Matt Kemp

TDR Partner

Choose a movie title for the story of The Digital Ring...

Field of Dreams. Lame I know…but, it is true. Working with my brother and Nick feels like a dream (most of the time). If we build it, they will come…clients and employees.

Nick Ring

TDR Partner

If you could have dinner with three people (past or present) - all together… who would you choose?

I’d pick Elon Musk, Nikola Tesla, and someone who could give me some insider info into Area 51, UFOs, and aliens. Not sure who that is - but it should make for one interesting dinner!

Nick Perkins

Chief Strategy Officer

If you were a stand-up comedian, what unusual topic would you base your entire routine on, and how would the audience react to your offbeat humor?

An entire schtick on 19th-century philosophy would be hilarious. I’d write/perform my routine in the style of James Acaster or Bo Burnham, pulling at the strings of absurdity, irony, and self-awareness. There’s a niche/Nietzsche pun I could include here, but since I couldn’t come up with any, I don’t see my comedy career taking off any time soon.

Kathryn Wundrow

VP of Accounts

If you had to eat one meal every day for the rest of your life, what would it be?

Vegetarian poke bowls!

Bess Donoghue

Director of Accounts

Which fictional character would you like to shadow for one week?

I’d love to see a blend of Leslie Knope’s determination, Ted Lasso’s enthusiasm, Mindy Lahiri’s passion, and David Rose’s ingenuity.

Jack Morrison

Account Executive

What is your most overused word/phrase?

“100%” - If I agree with you about something, chances are you’re going to hear me say, “100%”

Marlies Hooten

Account Executive

What’s the most random thing in your purse/wallet?

I’m a chronic thief of wet wipe packets. At any given time, I have at least 3 Buffalo Wild Wings wipe packets.

Victoria Fadden

Account Executive

If you could host a talk show, who would be your first guest?

Oprah — why not learn from the best?

Katie Morenz

Senior Graphic Designer

If you could switch lives with any fictional character for a day, who would it be and what's the first thing you'd do in their world?

Hopefully animated fictional characters count, since Rainbow Brite has been my personal hero since around 1984. The first thing I would do in Rainbowland would be to grab Starlite’s mane, flip myself up and gallop onto a rainbow through the stars.

Rose Ross

Senior Graphic Designer

If you could have a never-ending supply of one type of food or drink, what would it be, and how would it impact your life?

Chocolate. Dark Chocolate. In my coffee, on my fruit, as a snack, in my mole sauce–everything everywhere chocolate.

Bailey Wolf

Associate Graphic Designer

What era would you time travel to if you could?

I would love to go back to the 1920s because I just love the fashion that went alongside this era (flapper girls in the Great Gatsby). But the 20s fashion aside, I also think it would be fun to pull a Back to the Future moment and be able to go to any decade!

Jimmy Penlesky

Web Developer

Do you believe in aliens?

If aliens believe in us, then yes.

Walther Alvarez

Web Developer

Is a hotdog a sandwich? Why or why not?

As a self-proclaimed “Sandwich Aficionado,” absolutely not. A sandwich requires 2 separate pieces of bread…it’s a taco if anything…

Ben Turner

Sr. Paid Digital Manager

What would be your superpower if it was based on your most useless skill?

I have a pretty good internal clock, so I guess my superpower would be to always know the exact time down to the millisecond. With this superpower, it’s likely I would end up serving as the United States’ primary timekeeper replacing the atomic clock in Colorado.

Brennen Keene

Paid Media Manager

If you could eat only one food for the rest of your life, what would it be?

I would have to say fried chicken. You can honestly eat it at any time of day, and I’m always in the mood for it, especially if it’s from Popeyes!

Katheleen Peckham

Paid Digital Coordinator

What’s your favorite emoji to use and why?

I love the 🫡 emoji because it can be used in so many scenarios, both genuinely and sarcastically. I use it the most in place of the thumbs-up emoji - I feel like it’s the Gen Z way of saying “Okay! *thumbs up emoji*”

Riley Krutza

SEO Manager

If you could eat only one food for the rest of your life, what would it be?

Assuming no health implications and no loopholes through high recipe variation, I might have to go with bread and butter. Have you ever heard someone say that they don't like bread and butter? "Bread and butter might be, outside of maybe pizza and chocolate, the best food in the invention of man."

Scott Mailheau

SEO Manager

If you were stuck on an island, what three non-essential things would you bring?

A hammock, a good book (probably the full Lord of The Rings trilogy), and a guitar. I don’t know how to play guitar but I’d have all the time in the world to learn.

Caitlin Jagla

Director of Creative Services

If you were a font, which would you be?

Comic Sans . . . just kidding. I'd say Helvetica: I adapt easily to different projects and teams and I'm known for clear communication and practical solutions, reflecting Helvetica’s versatility and popularity.

Liberty Harris

Copywriter

Are you spring, summer, fall, or winter? Why?

Fall! It’s really a time to slow down, embrace change, and spend time with loved ones. I’m a super sentimental person, so that really resonates with me. On a less serious note, I love football, cool weather, comfort food, and wearing earth tones – so it’s kind of a no-brainer.

Jared Staege

Senior Project Manager

Gryffindor, Hufflepuff, Ravenclaw, or Slytherin?

I would say Hufflepuff, since my top values match the house values: dedication, patience, and loyalty — just like my guy Cedric Diggory (RIP).

Want To Join Our Crew?

We’re always on the lookout for strategic, creative, hard working people with a range of backgrounds and experience levels. Check out our open positions — we’re excited to hear from you!

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Madison Headquarters
821 E Washington Ave #200
Madison, WI 53703
608.836.7464