Streamlining Agency Success with Curiosity | Reuben Shoub from Workamajig

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All right, everyone. Welcome to today’s episode of Pathmonk Presents. Today we are joined by Reuben. He is the Marketing Manager at Workamajig. Reuben, welcome to the show.

Reuben: Thank you, Rick. Thank you, Pathmonk. It’s definitely an honor to be on the show.

Rick: We love to have you here. Reuben, let’s start with the basics. What’s the big idea behind your company? If you were explaining it to a friend over coffee, how would you describe what you do?

Reuben: Sure. Workamajig serves the advertising industry—especially recently, with so much new software out there, especially in the age of AI. It’s sometimes very hard to find your footing in the industry and find what really serves you, as opposed to getting lost in all the options. Workamajig is very specific software, built by creatives for creatives, serving the advertising agency space—both in-house teams and external agencies.

We’ve been in the market for about 25 or 30 years. We use that experience to figure out exactly what processes are most beneficial for agencies and built a full, complete suite of software to give them exactly what they need and when they need it.

Rick: You guys have been around for so long—you must know exactly what these agencies need and how those needs have evolved over the years. That’s a compelling value proposition.

Reuben: It’s amazing to be working shoulder to shoulder with people who’ve been in this industry for decades. Some folks have 25 or 30 years of experience. All the issues that come up—they’ve been there, they’ve seen it, they’ve done it. There’s a huge curiosity in our company that we really pride ourselves on. We’re always looking for new ideas, features, angles. That combination of history, knowledge, and curiosity has been driving Workamajig for the past 25 years.

Rick: Is there a specific kind of agency where your product really shines? What problems do you help them solve?

Reuben: There definitely are certain types of agencies that benefit the most. Workamajig has two primary components: project management and a full suite of accounting features. When you have those two running in the same system, and the whole company is working within it, the reporting you get is phenomenal. You can drill down to as much detail as you want.

Smaller agencies, maybe five to ten users, still get benefits, but the real value starts to shine from 10, 15, or 20 users and up. That’s when people start living in the software. It becomes their bread and butter.

We often see surprises in year-end reports. Agencies think a particular client is their most profitable, but when the data comes in, it turns out that client is actually draining resources due to changes and complexities. And then you find other clients who don’t get much attention but are actually super profitable. That visibility is invaluable.

Rick: Having that kind of data is powerful. It lets you strategize around what’s working and what isn’t. Any other key benefits?

Reuben: Yes—estimates. When you have all the data in one system, you can pull estimates quickly and accurately. You know what the project will need, what it’ll cost, and how you want to charge for it. That’s another huge benefit.

Rick: So how do new clients discover you? What marketing channels have become your go-to?

Reuben: At Workamajig, we really consider our clients as partners. The relationship starts long before they become a client. Probably the most helpful way to meet new clients has been in-person events. We go to a lot of industry group events. We love hanging out with our current clients and meeting new ones.

Referrals and word of mouth are huge. It’s not about a fancy ad—it’s about hearing from someone who’s already seen the value. Once we have the chance to show what we do and who we are, the relationship grows from there.

We have a phenomenal sales team, all with deep industry knowledge. The average tenure at Workamajig is about ten years, which is amazing. Their experience makes a big difference.

Our website is another big entry point. We put a lot of effort into not just making it look good, but making it flow well. There’s a clear journey with grouped and structured information. Social media is also important for connecting and starting conversations.

Rick: That’s great. I love the mix of face-to-face and digital touchpoints. Let’s talk about your website for a second. What do you think actually makes a website convert?

Reuben: Sometimes I visit beautiful websites that just leave me feeling overwhelmed. That inspired us when we rebuilt ours a few months ago. We wanted it to be pleasant but not boring—engaging and thought-provoking, but clear.

Testimonials matter, but where you place them matters too. The site has to be clear and connect emotionally. When someone lands on your site, it means something isn’t working for them. Something’s bothering them. You want to touch on those pain points while offering something positive, something beautiful.

Think about who your visitor is. Build a persona. What’s bothering them? Then answer their questions in a thoughtful, gentle way. Use colors that are pleasing, build a journey from top to bottom, and keep it a positive experience. No scare tactics—just genuine help.

Rick: That sounds simple on paper but so hard to execute. Let’s shift gears. I’d love to learn more about you. What’s a typical workday like?

Reuben: I’m relatively new to the industry—about three years in. It took six to twelve months to find the projects that really resonated with me. My day involves a lot of meetings. I’m a people person. I actually flew 5,000 miles just to meet clients at a training event. I didn’t need to be there for any technical reason—I just wanted to connect in person.

My main responsibility is managing our partnerships—both with technology partners and industry consultants. We do a lot of content together: videos, webinars, podcasts, articles. I also help with the website, social media, and planning events for our users. I love giving value and creating connections.

Rick: That’s amazing. And it’s clear you care deeply—flying that far just to connect speaks volumes.

Reuben: It was a phenomenal experience. And I couldn’t do any of it without an awesome team behind me. Everything we do is collaborative.

Rick: That’s great. Let’s do a rapid-fire segment. Ready?

Reuben: Let’s go.

Rick: Watching or reading?

Reuben: For work, watching. For entertainment, reading.

Rick: Fair enough. What’s the latest piece of content you picked up, and what stuck with you?

Reuben: A webinar on company culture. The line that stuck with me was “culture starts from the top.” That really resonated. If leaders set a strong tone, it trickles down.

Rick: Magic wand time—what’s one marketing frustration you’d fix instantly?

Reuben: Analyzing my data. That one’s easy.

Rick: What about a repetitive task you’d automate forever?

Reuben: Setting up client meetings efficiently. I’m sure it could be done better, but I haven’t cracked it yet.

Rick: What advice would you give your past self starting out in marketing?

Reuben: Explore. I was too afraid to try new things early on. Some projects didn’t work, but I learned. Be open to people, to projects, to new ideas. Try things one at a time and see what works.

Rick: Excellent advice. Keep learning. Final question: what’s the one thing people should remember about the work you’re doing at Workamajig?

Reuben: Don’t be complacent. Whether it’s software, people, or process—stay curious. If something’s not working, be open to change. If your mind is open, the answers will come.

Rick: That’s a beautiful thought to end on. Where can people find you?

Reuben: Workamajig.com. Or reach out to me directly—reubens@workamajig.com. Always happy to talk.

Rick: Thank you, Reuben. This was great.