Q&A With Jen Robinson, CTO Of Digital Media Solutions

With a career dedicated to scaling platforms and guiding organizations through growth and transformation, Jen Robinson joins DMS as Chief Technology Officer at a pivotal time of innovation and momentum. Known for blending strategic vision with hands-on execution, Jen has led technology teams across startups and public enterprises to deliver secure, scalable and results-driven solutions.

In this Q&A, Jen shares her perspective on AI, innovation and what excites her most about building technology as a true growth engine for DMS.

Q: What excites you most about leading technology at DMS right now?

Jen: DMS is beginning a really exciting new phase of growth. We have an incredible foundation to build on — a solid business model, strong relationships with our customers and a great team. With the fundamentals in place, we’re positioned to accelerate by scaling our advertising capabilities, expanding our owned and operated properties and using data and AI automation to optimize yield for advertisers. It’s an exciting moment to bring technology to the forefront as a true growth engine for the business. 

Q: AI is such a major focus for our industry. What role do you see it playing in performance marketing in the next few years?

Jen: I see AI significantly reshaping the performance marketing industry in the next few years. We have already seen a wave of marketing optimizations driven by generative AI and are about to see the next phase with agentic AI. 

As marketers learn to harness their power, AI agents will take on more autonomous execution roles in campaign management. We will begin to see optimizations happen at a speed and scale that humans can’t match, particularly in dynamic or real-time environments. 

Over time, the competitive advantage will go to marketers who master agentic workflows, integrate their data stacks and allow agents to continuously fine-tune strategies. We are positioning DMS to lead in this new phase. 

Q:  What’s one misconception about AI or emerging tech that you think people get wrong?

Jen: A big misconception about AI is that it’s a plug-and-play solution that can instantly transform a business. The truth is that AI is only as effective as the people, processes and tech driving it. Without clean data, clear goals and thoughtful integration, even the most advanced models won’t deliver meaningful results. The real differentiator isn’t having AI, it’s how well an organization operationalizes it to drive smarter decisions and better outcomes. Success requires diligence, experimentation and a culture that’s ready to learn and adapt alongside the technology.

Q: How do you approach building a technology team that’s both innovative and grounded in real-world application?

Jen: I believe the key to building a technology team that’s both innovative and grounded is creating the right balance between exploration and execution. That means fostering a culture where curiosity and experimentation are encouraged, but always anchored to clear business goals and measurable outcomes. 

I look for people who can think creatively but also know how to turn ideas into scalable, reliable systems. Ultimately, it’s about building a team that’s not just excited by what’s possible but deeply focused on delivering technology that drives growth and value.

Q: When you’re not focused on technology and growth, how do you like to spend your time?

Jen: I’m an athlete. I played two varsity sports through college. Now that I’m living back in my hometown of Pittsburgh, I love to play ice hockey, golf and ski with my kids. 

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About the author

Digital Media Solutions

Digital Media Solutions, LLC (DMS) drives better business results by connecting high-intent consumers with advertisers across our core verticals: Insurance (auto, home, health) and Education. Our innovative solutions help consumers shop and save, while helping our advertisers achieve above average return on ad spend. Learn more at https://digitalmediasolutions.com.