Craft Class: Stories of Creativity and Innovation

Welcome to Craft Class, where we spotlight the creative thinkers and team builders behind CRAFTSMAN+—the people shaping our culture and powering our growth. This edition features Jess Jackson, Vice President of People Operations, whose gift for connection, commitment to integrity, and all-around hype energy has helped cultivate one of the most vibrant, human-centered cultures in the digital advertising space.

Since joining the company in 2021, Jess has worn many hats: recruiter, people strategist, party planner, counselor, cheerleader, and trusted confidante to just about everyone. She’s the one you call when you’re celebrating a big win—or when life throws you a curveball. She’s everyone’s sidekick and best friend, and she wouldn’t have it any other way.

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From Real Talk to Real Impact

Before I joined CRAFTSMAN+, I was working in recruitment and community development. I felt like I’d hit a ceiling at my current job and I was determined to level up in my career. I began my search on Linkedin and stumbled across a recruiter role at a company called CRAFTSMAN+. I thought it was a power tool company! But when I researched, I quickly realized it was something way cooler. I texted my brother who works in advertising, and he took one look and said, "This place looks legit. You should go for it."

When I interviewed, I decided to just be me. No filters. No professional facade. Just real talk. I was honest about what I could take on and what I couldn’t. I didn’t say “no,” I said “yes, if”—yes, I can do this if I have the right support, or if I have six months instead of three. That phrase stuck and turned out to be something that our CEO Alex led with as well. In fact, it became a kind of unofficial motto during those early days, and to this day, it's a mentality we return to often.

That approach has become a cultural touchstone here. It’s not just about being agreeable, it’s about being thoughtful. Collaborative. Human.

Leading with Ownership, Backed by Trust

At first, I came in as a recruiter, but soon I was tapped to lead People Ops. I didn’t have all the answers. But what I did have was a strong sense of ownership and the confidence that I would figure it out. Alex and the leadership team believed in me—and that belief transferred. It gave me room to learn, to lead, and to make mistakes without fear.

One of the first things I worked on was defining our company values. We already had a mission, but I believed we needed something more to ground us. Over the years, we’ve honed in on five key values: ownership, accountability, integrity, curiosity, and action. Authenticity is the value that underpins everything else. I see it in the way we show up, speak up, and support one another.

The Power of Global Connection

Building a vibrant, connected culture in a remote environment isn’t easy. But, it’s possible, and honestly, it’s one of our biggest strengths. Because our team is global, we’re constantly exposed to new trends, different ways of thinking, and perspectives that make us better creatives and collaborators.

We use Slack to keep connection alive. Channels like #watercooler, #craftsmanpets and our quarterly X-Collab meetups help foster community. We also rolled out the EOS (Entrepreneurial Operating System) framework across the company to keep everyone aligned. It might not sound sexy, but regular L10 meetings have brought consistency and clarity to how we work together, especially as we’ve grown.

Showing Up for Each Other

As our team has grown, so have the real-life friendships. One of the things that fills me with the most pride is seeing teammates go out of their way to meet up—on vacations, during stopovers, or even planning whole trips just to visit each other in person. These spontaneous micro-meetups happen because people genuinely care about one another.

I joke that I have sidekick energy, and it’s true. I love supporting people behind the scenes, hyping them up, and helping them shine. If I’m everyone’s work best friend, I’m doing my job right.

Living Our Values, Every Day

At CRAFTSMAN+, we don’t just talk about values, we live them. Whether it’s implementing gender-inclusive language in our policies or celebrating global holidays together, we’re constantly working to build a culture that’s inclusive, human, and real. That’s the core of it: trust, action, and authenticity.

Let’s Build Something Real Together

At CRAFTSMAN+, we don’t just create ads, we build experiences that connect. Behind every campaign is a team of curious, compassionate, and wildly talented people who bring their full selves to the table.

If you’re looking for a partner who values authenticity, moves with integrity, and isn’t afraid to say “yes, if,” we’d love to work with you.