327: Behind the Scenes of Strategic Marketing with Jennifer Osterhouse: Fan Favorite Replay

ByAliceAnne Loftus

What does it really take to create a cohesive, memorable brand experience at a live event? In this episode, I sit down with my dear friend and fellow Leading Lady Ambassador, Jennifer Osterhouse, to pull back the curtain on everything that went into creating the stunning marketing materials for our recent We Lead conference. Jennifer is a graphic designer with over 25 years of experience, and she’s the creative genius behind all of the Leading Lady’s marketing assets. You’ll hear about the strategy sessions, timeline, and thoughtful planning that went into every single piece, plus why certain design choices (like those Leading Lady bags people spot in the wild!) make all the difference in how your business is perceived and remembered.

This conversation isn’t just about an event—it’s about the bigger picture of how you show up for your business. Jennifer and I discuss the importance of investing in quality swag that people actually want to use, creating evergreen marketing pieces that serve you again and again, and why planning your marketing assets months in advance will save your sanity.

Hi there. You’re listening to the Leading Lady podcast. I’m your host, AliceAnne Loftus, and I’m a certified professional coach specializing in leadership and work-life balance. I work with clients to shift their limiting beliefs, insecurities, and self-doubt. This podcast will be filled with tools and strategies to help high-achieving women like you feel connected, empowered, and in the lead of your life, both personally and professionally. Let’s transform your life starting now. Lead yourself. The rest will follow.

Hi there, leading ladies, and welcome to today’s episode. Today I am joined by fellow Leading Lady Ambassador and dear friend, Jennifer Osterhouse. Jennifer is a graphic designer with over 25 years of experience in direct response design, publication design, and marketing material design. Woo! Girl, you are an expert. She helps clients up-level their marketing materials by designing custom-branded print and digital marketing assets to promote the products and services that your business has to offer. She believes in quality design, clear messaging, and professional standards in every project she does. Her passion is helping businesses put their best foot forward with unforgettable, eye-catching graphic designs. Yes, you do, and I can speak firsthand about this because Jennifer also does all of the Leading Lady marketing assets, and that’s what we’re going to be talking about today. Because, Jennifer, thank you so much for being my guest today.

Jennifer: Thank you for having me. And whew, that was a lot. That was a mouthful.

AliceAnne: It was. But you. Yay, you! What an amazing career you were having. But for today’s episode, we’re going to talk about what went on behind the scenes as we just were coming off the heels of the We Lead conference. And I don’t think a lot of people know or maybe understand the work that happens prior to an event like that, specifically around creating the marketing materials. And some of the greatest feedback I got from the We Lead conference is just the continuity of the branding and how everything fit together. Everything complimented each other. They said, listen, the marketing of this, the assets that you had there, it was a Leading Lady event, even though we were in a different venue.

Jennifer: Yeah. And I know I had somebody come up to me and say, “It’s almost like you transplanted Leading Lady from Annapolis to Baltimore. Like Leading Lady came in and sort of, like, branded the place.”

AliceAnne: I was gonna say, threw up all over the place. But because our branding was everywhere, it was an empty bank building and we made it look like Leading Lady had lived there forever.

Jennifer: Yeah.

AliceAnne: Yes. Yes, yes.

Jennifer: Yeah.

AliceAnne: So have you caught your breath since the event?

Jennifer: Yeah, I have caught my breath. And I will say, and I know I’ve shared this with you before. It was a little stressful with all the moving pieces, but it was also really fun. So one thing that I love about design, and I’ve always loved when I do publication design, it’s almost like taking a thread and weaving it through all the pages of the piece so that, like you said, it has continuity, it has branding, and it all like goes together. And that concept also plays out in an event because like, I know with you and Jaden and I sat down initially and I mean, we had several meetings, but like we’ve talked about the first meeting and then we would talk about one thing and then three more things would evolve off of that. And then, oh, wait, we needed this. And, you know, from a huge retractable sign to the program itself, the magazine that we created, which is—

AliceAnne: Absolutely stunning, absolutely stunning magazine.

Jennifer: And I think that that served its purpose so well. I feel like we did suc

In Today’s Episode, We Discuss: 

  • The secret to making your brand “explode” in any venue and create instant recognition
  • Why one specific marketing piece became the most valuable takeaway from the entire event
  • The strategic difference between event-specific materials and evergreen assets that save you money
  • What the “Batman symbol” approach to swag can do for your brand visibility
  • The one question you must answer before creating any marketing material for an event
  • Why a marketing strategy session might be the best investment you make for your business
  • The planning timeline that ensures you never scramble at the last minute for event materials
  • How to make your brand so recognizable that people identify it without seeing your business name

If this episode inspired you to elevate your own marketing materials and event presence, don’t wait! The time to plan for 2026 is now. Connect with Jennifer Osterhouse to schedule your own marketing asset planning and strategy session.

Resources Mentioned: 

Schedule a Call with Jenn

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AliceAnne Loftus

AliceAnne Loftus is a certified professional coach and founder of Leading Lady Coaching in Annapolis, Maryland. She spent nearly two decades running childcare businesses before launching her coaching practice, and that hands-on experience is at the center of everything she teaches. AliceAnne works with women entrepreneurs who want to grow their businesses without burning out, offering private coaching, group programs, and an in-person community called The Collective. She's the author of "Take the Lead" and lead author of the "We Lead" series, and she hosts the weekly Leading Lady Podcast. She also leads the Leading Ladies Facebook Group, a community of nearly 7,000 women supporting each other through the real stuff of business ownership.

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