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Welcome To Digital 2.0:
The Modern Digital Executive Interview Series.
Episode 10 / November 8, 2022
Digital 2.0 Episode 10:
Sam Chlebowski, Co-Founder at
In this episode, Sam Chlebowski, Co-Founder at talks about finding balance and trimming the fat without losing what makes your product unique and more.
Digital 2.0 is an interview series dedicated to interviewing the best and brightest senior digital executives around the world that have taken a stance on the importance of Digital within their organizations and are helping everyone understand the role of technology in our everyday lives.
Episode 10 / November 8, 2022
Finding Balance, Trimming the Fat, and Using Digital to Disrupt: A Conversation with Co-Founder Sam Chlebowski


At only 30 years old, Sam Chlebowski is a relatively young founder, but he’s certainly not inexperienced. In the last decade, he’s served as a lead developer, director of sales and customer happiness, and vice president of sales and marketing for Brighter Vision, a web design and marketing firm.

There, he played an integral role in growing the company from a team of three to 35. In addition, he single-handedly closed 1,500 new accounts while increasing the company’s ARR from $2.5 million to over $4 million. He’s also served as a marketing manager for EverCommerce, head of growth at Castos, and is now the co-founder and VP of marketing at

If you’re new to, it’s a software platform that helps designers, web developers, and marketers keep projects moving and provide a premium client experience by combining project management with client collaboration in one simple dashboard. Using, businesses can streamline and automate their workflows while making it easy for clients to upload files, provide feedback on deliverables, and track the status of their projects through a simple client portal.

I wanted to find out what Sam’s learned about transforming companies digitally, ask him about emerging tech trends and trendsetters, and find out why he’s more interested in being “disruptive” than “innovative.”

Here’s what he had to say.

Biggest Lessons Learned About Transforming Companies Digitally

Sam has accomplished a lot in a little time. As someone who played an integral role in growing small companies and dominating niche markets, I wanted to know what he’s learned over the last decade.

His response? Find balance and trim the fat without losing what makes your product unique.

You’ve probably heard the phrase, “kill your darlings.” That was William Faulkner’s advice for aspiring writers: You may love your meandering side plots and witty turns of phrase, but if they’re standing between you and the reader, get rid of them.

Designers struggle with the same thing, Sam explains. So how do we figure out which MVP “darlings” to cut and keep? “If you don’t trim, you can’t ship,” he says. “Yet, at the same time, you must protect the core functionality that makes your product your product.”

But it’s even more complicated than that, Sam tells me. We live in a fast-moving world Faulkner couldn’t have conceived of.

Designers must get something tangible built in the shortest timeframe possible. If it takes three years to get an MVP out, it’ll be obsolete before it’s even brought to market.

Then there are the table stakes, right? The base level of functionality you had in your mind when you started gets updated once you start talking to users.

It’s tricky business, and while Sam doesn’t have a silver-bullet solution, he’s clear about one thing: “It’s all about balance.” And to find it, sometimes you must take Faulkner’s advice.

How Sam Defines Innovation

If organizations want to do more than keep pace, they must innovate. But how do they do it? And what does “innovation” really mean?

“I hear ‘innovation,’ ‘transformation,’ and ‘modernization’ all the time,” says Sam, “but I file all those words under the same umbrella. I’m more interested in being disruptive,” he tells me.

To explain, Sam referenced the digital messaging tool Slack. Slack eliminates communication barriers in a way that email can’t.

All Slack content is searchable, so there’s no need to dig through forwarded emails to find content. Plus, you can share calls and clips, message in real-time, and manage automated workflows all within one place.

Slack took something sluggish and turned it on its head. Even more interesting is how Slack has permeated our culture and language.

“If you would’ve said, ‘Hey, Slack it to me,’ a decade ago, no one would’ve understood what you were talking about,” Sam says. “Now, I can use that language freely with almost anyone. And even if they don’t use Slack, they still know what I’m talking about.”

That’s the kind of innovation Sam achieves with his task-management tool

“I want to change how people work and give them tools that didn’t previously exist,” he says. “And if we’re not helping people increase revenue and become faster and more efficient, we’re probably not innovating, transforming, or modernizing anything—and we’re certainly not being disruptive.”

Challenges in Building a Brand-New Product

Whose voice are we listening to? Is it our ideas or our customer’s ideas?

Companies That Are Surprising

Like them or not, The New York Times has a fascinating story. And Sam and I both admire how The Times went from being what Sam calls “one of the most stodgy traditional print publications to a leading digital enterprise.”

Fifteen years ago, The New York Times had a newspaper and a website. You could log in and read the news, but nothing particularly groundbreaking was going on. Then, a few years later, the publication made a drastic pivot into the digital space.

Now, the organization has a crossword app that people play on their phones. In addition, their podcast, The Daily, is one of the most listened-to programs in the country. “It’s obvious that somebody was really intentional about this change,” says Sam.

Not long ago, people said, “journalism is dead.” And it seemed true. Publication after publication tanked. But The New York Times was like, “Hey, hold my beer. We’re going to transform the journalism space.” And that’s exactly what they did.

So you don’t have to like them, but who’d you rather be? The New York Times or the guy holding the beer?


What sustains an organization? Is it strategy, products, people, or leadership? These might do it for a while, but when one wavers, the entire house of cards crumbles.

Without a healthy culture and cross-organizational buy-in, organizations cannot thrive, no matter how strong their strategy, product, or people are. So what’s Sam’s advice for creating a vibrant work culture?

Create it. Or it’ll create itself.

“Work culture doesn’t just exist,” Sam tells me. “You need to talk about it, write it down, and share it, so people understand your values and expectations.” And if you want that mission to sustain you for the duration, you must facilitate cross-organizational buy-in.

“At, we encourage risk-taking,” Sam says. “As long as team members take risks that align with our mission, we’re on board whether it works out or not.”

So if a team member creates a marketing initiative or releases a feature that doesn’t create value, no problem. Of course, success is preferred, but in Sam’s view, falling short is okay when you’re working with intentions that align with the organization’s culture.

But team members can’t take effective risks unless they have a working philosophy.

That’s why Sam has worked so hard to establish a clear vision and a cohesive culture everyone buys into.

Biggest Impact on Digital Innovation for the Next 10 Years

"We want to expand and we want to grow bigger."

Handling Change in Teams

"You have to be very practical and you have to be very mindful of your culture."

Digital 2.0 Hot Seat: Real, Hype, or WTF

I closed our conversation with a series of rapid-fire questions covering four of my favorite topics: the Metaverse, crypto, Elon Musk, and remote/hybrid work.

Are they real, hype, or do they just make you scratch your head and say, “WTF?” Here’s what Neil had to say:

The Metaverse:

“Living in a visual simulation for days on end isn’t real. But the Metaverse could be a digital accompaniment or package that allows organizations to track data through a software dashboard. I’ve been digitizing things for over a decade, so if we’re talking about the Metaverse as a digital component, I think it’s real.”


“Blockchain technology and digital ledgers are real, but crypto is hype. I’ve spent enough time understanding the intricacies underpinning our legal system, not to mention the securities on the financial side. So it’s going to be a lifetime before we have a truly decentralized currency that’s adopted by the masses.”

Elon Musk:

“Look, Musk has the opportunity to be solidified and stand amongst the truly elite. He could be the Einstein of our generation. Yet, he’s focused on publicity and NFTs.

Musk is the perfect example of why we need to shift the narrative of entrepreneurship. You’ve got someone who built an incredible company but chooses to embark on public, Kanye-West-style escapades to shift markets up or down instead of propelling the industry forward.

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