Wicked: B2B Marketing Lessons on Reframing the Narrative with Chief Marketing Officer at Flywire, Allison MacLeod

When your audience thinks they already know your story, the boldest brands flip the script and earn their attention in the process. 

That’s exactly what happens in Wicked, the smash-hit film adaptation that reimagines one of pop culture’s most iconic villains. In this episode, we explore the marketing lessons behind it with the help of our special guest Allison MacLeod, Chief Marketing Officer & GM of US Education at Flywire.

Together, we explore what B2B marketers can learn from reframing brand narratives, building fan-level community, and executing with bold, high-stakes detail that actually gets noticed.

About our guest, Allison Macleod

Allison Macleod currently serves as Chief Marketing Officer & Head of US Education at Flywire (Nasdaq: FLYW), a global payments enablement & software company. At Flywire, Allison leads global marketing and revenue operations, & US Education sales, relationship management & pre-sales. She played a key role in guiding Flywire to a successful IPO in May 2021.

Allison brings nearly 20 years of experience with a background spanning marketing and revenue-focused roles. Prior to Flywire, she spent seven years at Rapid7 (Nasdaq: RPD), where she played a pivotal role in building and scaling demand generation, business development, and analytics. Before that, she held various digital and field-based positions at Forrester, including launching the marketing function in EMEA.

Outside of work, Allison sits on the Board of Trustees of the Massachusetts Technology Leadership Council and serves as a strategic advisor to early-stage companies through F-Prime & Underscore VC.

What B2B Companies Can Learn From Wicked:

• Reframe what they think they know. Wicked works because it flips a legacy story on its head. The same power lies in brand repositioning. “How do you really reframe what people think they know about you and your brand,” Allison says. Whether it’s entering new markets or expanding product lines, your biggest unlock might come from telling your old story in a completely new way.
• Community is your flywheel. Wicked isn’t just a show, it’s a movement. Audiences don’t just watch it, they live it. That level of advocacy isn’t accidental. “How do you really cultivate that community, whether that's your clients, the advocacy, and make people… feel that deep passion for what you do,” Allison asks. In B2B, fandom might look like retention, referrals, or customer-led storytelling, but it starts with emotional connection.
• Be bold and unforgettable. Every production choice in Wicked is a masterclass in attention to detail. From the live vocals to the stunts, they took creative risks that resonated. “How do you be bold and unforgettable,” Allison says. The safest move in saturated categories? Standing out.

Quote

“I think that's sort of the lesson and the beauty in this, taking something that everyone already thought they knew, and they thought they knew the story… and completely reframing it. And I think that’s where you just think of us as businesses, us as consumers… there’s so much clutter. So the brands that stick out and do things differently, and even if it is trying the same channel but in a different way, there’s so much power in that."

Time Stamps

[0:55] Meet Allison MacLeod, Chief Marketing Officer & GM of US Education at Flywire

[01:05] Why Wicked?

[02:29] The Role of CMO at Flywire

[04:00] Breaking Down of Wicked

[09:22] B2B Marketing Takeaways from Wicked

[21:54] The Appeal of Villains and Taking Risks

[23:37] The Power of Visual Design in Branding

[24:54] Marketing Strategies for Global Brands

[29:26] Flywire's Unique Differentiation Approach

[40:03] Final Thoughts and Takeaways

Links

Connect with Allison on LinkedIn

Learn more about Flywire

About Remarkable!

Remarkable! is created by the team at Caspian Studios, the premier B2B Podcast-as-a-Service company. Caspian creates both nonfiction and fiction series for B2B companies. If you want a fiction series check out our new offering - The Business Thriller - Hollywood style storytelling for B2B. Learn more at CaspianStudios.com. 

In today’s episode, you heard from Ian Faison (CEO of Caspian Studios) and Meredith Gooderham (Head of Production). Remarkable was produced this week by Jess Avellino, mixed by Scott Goodrich, and our theme song is “Solomon” by FALAK. 

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