In honor of Women’s History Month, RedTree Web Design partnered with AMA Pittsburgh to launch a new panel series built for one purpose: real conversations about strategy, career growth, and leadership, without the polish that usually gets in the way. This first installment was designed specifically for women and marginalized genders in marketing, and it won’t be the last.
The event sold out two weeks before doors even opened. By the day of, the room at Fred Rogers Productions was full of mid to senior-level marketing women and non-binary leaders, ready to talk about the parts of leadership that rarely make it into a keynote.
Why This Event, Why Now
Women make up roughly half of all marketing roles, yet only about 20% reach the C-suite. That gap doesn’t close on its own, and it doesn’t close through feel-good panels either. This one was built differently: tactical strategies and executive power moves, in a space designed exclusively for women and marginalized genders in the industry.
The demand made the case for itself. Tickets sold out so quickly that AMA Pittsburgh increased capacity, and even then, requests for extra seats kept coming in. It’s a clear signal that Pittsburgh’s marketing community has been waiting for a space like this.
Hosted at Fred Rogers Productions, On Purpose
The venue wasn’t just a nice backdrop. Fred Rogers Productions carries a legacy built on kindness, acceptance, and meeting people exactly where they are, values that mirror what this panel set out to do: create room for women and marginalized genders to show up fully and be heard.
That spirit shaped even the smallest moments of the day. As an icebreaker, panelists were asked to share a favorite Fred Rogers moment, and the answers stretched well beyond nostalgia. Some spoke to childhood memories of the show itself. Others reflected on watching their own kids discover Mister Rogers’ Neighborhood for the first time, or on what Fred Rogers Productions’ work means to them now, as parents and as professionals. It set an honest, human tone before the strategic conversation even began.
Meet the Panel
Moderated by Meesha Gerhart, Founder & CEO of RedTree Web Design, the panel brought together four leaders spanning agency, corporate, nonprofit, and entrepreneurial marketing careers:
Aleya Crable Jennings, Director of Corporate Sponsorships and Individual Giving at Fred Rogers Productions, with a background leading large-scale advertising campaigns and a deep commitment to empowering women through her board work with Girls Inc. of Greater Pittsburgh.
Robin DeSantis, Global Senior Communications Leader for Packaging Coatings at PPG, a marketing communications strategist known for building her career on storytelling.
Miche Riches, an award-winning Digital Strategy Director at Wall-to-Wall Studios, with over a decade of experience across agency, in-house, and freelance work in paid media and brand strategy.
Deanna Tomaselli, Vice President of Client Services and Director of Analytics & Client Engagement at The Motherhood, with nearly 20 years in PR and influencer marketing and national media placements to show for it.
Reframing “Balance” as Competing Priorities
Rather than avoid the topic, the panel broadened it. The conversation moved away from the idea of balance as some fixed, achievable state and toward the idea of managing competing priorities, day by day. One panelist described life as a pie: not about adding or subtracting slices, but restructuring them as priorities shift. Some pieces get bigger. Some get smaller. That’s not failure. That’s the job, and that’s life.
One of the most candid parts of the conversation started with a challenge to the premise of the question itself: why is “how do you balance it all” so rarely asked of men in leadership?
It’s a reframe with real value for anyone leading a team, a business, or a career: the goal was never a perfect equilibrium. It’s building the judgment to know which priority deserves the bigger slice this week, and giving yourself permission to shift it again next week.
AI as a Tool, Not a Threat
The panel also tackled a question every marketing leader is sitting with right now: how do you use AI without producing “AI slop”?
The consensus was clear. AI isn’t replacing marketing judgment, it’s removing friction around it: drafting emails to the right audience, organizing recaps, generating starting points for ideas, and speeding up execution. The strategic thinking, the voice, and the judgment about what’s actually worth publishing still has to come from a person. Treating AI as an efficiency layer, not a replacement for expertise, is what keeps content from becoming commodity content that readers (and search engines) can spot from a mile away.
Career Pivots and Power Moves
The panel didn’t shy away from the practical either. Discussion covered what prompted moves between corporate and agency roles (and back again), how those shifts changed each panelist’s approach to strategy, and how to evaluate the harder question: when do you stay in a role, and when do you go pursue something new?
Threaded through all of it was a theme about building a personal board of directors, the people outside your immediate team you trust for unfiltered career advice, and the intentional (or unintentional) work it takes to build access to that kind of vertical relationship, not just a peer network.
This Is Just the Beginning
The response after the event said as much as the panel itself. Attendees described a room where women and non-binary leaders stopped performing and started talking honestly, calling it a genuine safe space to say the hard things out loud. Others pointed to the specific moments that stuck: the reframe around priorities, the grounded take on AI, and the simple fact that a room full of marketing leaders at this level, gathered specifically for each other, hadn’t existed in Pittsburgh before this.
That reaction is exactly why RedTree helped bring this space to life, and why it’s just the first of many. Want to know when the next panel is happening? Follow RedTree Web Design and AMA Pittsburgh on LinkedIn so you don’t miss the announcement.
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