Currently Booking for 2025

Is a career-long strategist with a penchant for removing the mess in the creative process.

About

Kristin Rupert, founder

I have been a Content and Creative Strategist since before either of them were an established profession. I was part of the pioneer class, navigating the world of digital marketing as it was forming. I have seen the good, the bad and the ugly, something that can only be achieved via 15 years of professional experience working on major household and DTC brands. I have refined my speciality by merging my “stellar editorial skills” (a former boss said it, not me) and my astute ability to analyze data and distill insights, to become a 50/50 blend of art + science that helps pave a smoother path to conversion.

Like a true Creative Strategist, everything I have done in my career that led to founding Big Penny, was by design. I have always been very intentional with what jobs I took to ensure I was gaining experience with new and different projects, in order to become the most well-rounded strategist I could be. 

Born to be a strategist.
Making a living practicing creativity.

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Along with success, we have also bore witness to the bad and the ugly, something that can only be achieved with 15 years of experience working on Fortune 500 household brands all the way to DTC startups.

Along the way, I noticed a pattern: companies and agencies had a strong paid media and analytics team, and/or a strong creative team. What was lacking was the strategic bridge between them both. Once I entered the realm of DTC and E-commerce, that strategy component became even more important than before. 

“You learn more from the challenges than you do from the successes”

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we believe in transparency

Our
core
values

We apply a human-centric lens to everything we do so that our clients feel understood, and their customers feel seen.

We’re sharp, witty, quick on your feet, and can deliver firecracker energy in your work, comms, and strategy with ease. We’re also clever in our working style; utilizing tech + tools to work smarter, not harder.

We eschew corporate superficiality and deliver your work with a no-nonsense approach.


Having an appreciation for levity and a healthy perspective. We understand the importance of maintaining a sense of humor. We look for ways to make even the mundane enjoyable.

Authenticity

Cleverness

Empathy

Fun

Natasha Brito, founder of AUSTERE

“Kristin is by far one of the most prolific and calculated creative strategists I have come across in my career. Her ability to get to know a brand and instantly understand how it should be marketed in the digital landscape is unmatched. She is truly one of my secret weapons in the projects that we have at AUSTERE whether the client is a start-up or a Fortune 500. I love her holistic intuition as a marketer. You can’t teach that.” 

Christine Shannon, CMO of Ollie.ai

“Thank you! I loved our conversation. I will definitely reach out to meet again. Your input was so valuable!” 

Silver Medal, Social/Interactive Content

 Chicago Advertising Federation Awards

Speaker & Panelist, “Confessions of a Community Manager”

SXSW Interactive

Speaker & Panelist, “Building, Scaling, and Thriving as Solopreneurs”

Efficient Growth

Best Overall Editorial

Custom Content Council Awards

A few awards we're proud of

Let us remove the mess from the creative process.

Work With Us