Jessica Wolfson has spent her career at the intersection of creativity, data, and human insight. Known for helping organizations see opportunities differently and solve complex business challenges, she has led award-winning work recognized by organizations including Cannes Lions. Today, as VP of Enterprise and Partnership Marketing at Penn Foster Group, she leads marketing strategies that help businesses and organizations create more accessible pathways to learning and economic opportunity. Her instincts were shaped early. A former competitive sprinter, Wolfson learned from her coach to stay “pleasantly uncomfortable,” the idea that growth happens right at the edge of your comfort zone, not beyond it and not behind it. She’s carried that mindset into a marketing career defined by transformation, cross-functional leadership, and a curiosity that draws as much from psychology and behavioral science as from marketing itself.
Named to our Marketers to Watch list, Wolfson shared her insights on why strategic thinking will outlast AI proficiency, why clarity is the most important leadership muscle a marketer can build, and why the best lessons she’s learned as a marketer came from outside marketing entirely.
What book or podcast do you recommend to marketing leaders?
I actually consume surprisingly little marketing content. Marketing doesn’t operate in a vacuum, so I find more value in understanding people, leadership, decision-making, and culture than I do in keeping up with the latest marketing trends.
On the podcast side, I regularly listen to A Bit of Optimism with Simon Sinek, IMO with Michelle Obama, The Oprah Podcast, NPR’s Wild Card, and The Weekly Show with Jon Stewart. They all offer different perspectives on leadership, communication, curiosity, and how people make sense of the world around them.
I’m also an avid reader, but I have a personal rule: I alternate between fiction and non-fiction. I love the work of Adam Grant, Brené Brown, Mellody Hobson, Simon Sinek, and Scott Galloway. More broadly, I’m thrilled that academics are having a moment in popular culture. Some of the most valuable lessons I’ve learned as a marketer have come from psychology, behavioral science, and organizational research rather than marketing itself. Understanding how people think, connect, and make decisions doesn’t just make us better strategists, it makes us more creative.
How are you and your team currently using AI?
Like most marketing teams, we’re using AI to accelerate research, synthesis, brainstorming, content development, and day-to-day workflows. The productivity gains are real, and AI has quickly become part of how we operate.
However, what I’m increasingly focused on is not the technology itself but the human skills that make it effective. The difference between using AI to generate answers and using it as a strategic tool comes down to critical thinking. It requires knowing how to frame a problem, define an objective, ask better questions, challenge assumptions, and evaluate tradeoffs.
AI proficiency is not going to be the differentiator. Strategic thinking will be.
We’re seeing a clear distinction emerge between sloppy and strategic AI use in the market. AI adoption is quickly becoming table stakes and will likely be ubiquitous within the next year. As that happens, we’ll all get better at recognizing generic, uninspired output.
The people who stand out will be the ones who can apply judgment, connect disparate ideas, and bring original thinking to increasingly complex business challenges.
What’s a prediction you have for marketing over the next few years?
I think the distinction between marketing leaders and business leaders will continue to disappear. AI, automation, and technology will continue to make it easier to create content, launch campaigns, analyze data, and scale execution. That’s exciting, but it also means those capabilities will become less differentiated over time.
The marketers who stand out won’t be the ones with access to the best tools. They’ll be the ones who can connect business strategy to customer needs, identify the right problems to solve, and create alignment across functions.
As execution gets easier, judgment becomes more important. The most successful marketers over the next few years will be systems thinkers who can connect people, technology, data, and business outcomes in ways that create sustainable growth. As information becomes more abundant, discernment becomes more valuable. The ability to determine what matters, what doesn’t, and where to focus will increasingly separate good marketers from great business leaders.
What’s the most innovative or exciting project you’ve worked on recently?
One of the most rewarding projects I’ve worked on recently has been helping lead a broader transformation around how our organization thinks about growth.
What has made it especially meaningful is that I joined Penn Foster during a period of significant change. Before making recommendations or introducing new ways of working, I spent a lot of time getting to know the people behind the roles. Understanding their strengths, challenges, goals, and aspirations gave me a much better sense of what was possible.
The work has certainly involved strategy, operating models, and go-to-market transformation, but the most important part has been helping people stretch into new opportunities and see what’s possible for themselves. For me, innovation isn’t just about new ideas. It’s about creating an environment where people can grow alongside the business.
What’s the most pressing business challenge you’ve faced in the last year and what have you done to solve it?
The most pressing challenge I’ve faced over the last year has been balancing long-term transformation with short-term business needs. Most organizations recognize they need to evolve, whether that’s modernizing their go-to-market approach, adopting new technologies, or changing how teams work together. The challenge is doing that while still delivering results today.
I’ve spent a significant amount of time helping teams align around a shared vision, challenge long-held assumptions, and make decisions that support both immediate business objectives and future growth. That has required a lot of cross-functional partnership, particularly across sales, marketing, operations, finance, and technology.
One lesson I’ve learned is that transformation rarely fails because of strategy. It usually fails because of misalignment. My focus has been creating clarity, building consensus, and helping people understand not just what we’re doing, but why we’re doing it. When that happens, execution becomes much easier.
What leadership muscle is most important for marketers to exercise?
If I had to pick one, it would be clarity. The ability to define the problem before jumping to solutions.
Marketing leaders operate at the intersection of customers, revenue, technology, operations, and brand. We’re often asked to make decisions in environments where information is incomplete, priorities are competing, and the path forward isn’t obvious.
The ability to create clarity amid ambiguity has become one of the most important leadership muscles I exercise. That starts with curiosity: challenging assumptions, asking better questions, and understanding the root issue before rushing to solutions. When teams have clarity around the problem they’re trying to solve, they make better decisions, move faster, and align more easily around a path forward. As AI, technology, and business models continue to evolve, I think this skill becomes even more important. Information is abundant. Clarity is not.
What’s the most game-changing piece of career advice you’ve ever received?
The most game-changing advice I ever received came from my high school track coach. I was a competitive sprinter, and he would often ask, “Are you pleasantly uncomfortable?”
What he meant was that growth happens right on the edge of your comfort zone. Push too hard, too fast, and you get injured. Stay comfortable, and you stop improving. The goal is to find that space where you’re challenged enough to grow but not so overwhelmed that you break.
I’ve carried that lesson throughout my career. The most meaningful opportunities I’ve had have often been the ones that felt slightly beyond my reach. Whether it’s leading transformation, taking on a new role, or navigating ambiguity, I’ve learned to view discomfort as a signal that I’m learning and growing.
To this day, if I’m feeling completely comfortable, it’s usually a sign that I’m not pushing myself hard enough.
What gives you energy and inspiration outside of work?
What gives me energy is connection. Friday nights are Shabbat in our home. Nothing formal, usually pizza, a gratitude round robin, sharing something meaningful that happened during the week, and family movie night. Somewhere along the way it became my favorite part of the week.
I also love bringing people together. Whether it’s hosting friends for dinner, pairing a great bottle of wine with a meal, or introducing people who might not otherwise cross paths, creating those experiences is one of my favorite creative outlets.
We have a phrase in our house: “smile inducers.” It’s those moments that drive me. The Friday night traditions, the impromptu dance parties, karaoke sessions that have no business happening, belly laughs that leave your face hurting, and the people who make all of it possible.
Marketers to Watch is a recognition series to spotlight highly innovative and forward-thinking marketing leaders in the community. If you have someone you’d like to nominate for the series, apply here.
