She Built Adidas & Microsoft’s Strategy… Now It’s Her Turn - Jess Jensen (Ep. 40)
Today on the Fairy Boss Mother Show, I met with Jess Jensen, a marketing strategist who’s worked with corporate giants like Adidas and Microsoft before social media was even a thing.
Jess thinks she’s helping C-suite execs and small business owners at the same time… but what she doesn’t see is that her own positioning is stuck between two worlds. She has the pedigree of a global strategist, but she’s marketing herself like a freelancer.
Can I take a woman who built global brands and help her finally treat herself like one?
Let’s meet Jess Jensen.
If you are an entrepreneur or a small business owner and want your brand reviewed, apply for your very own brand audit here.
Watch the Episode:
See Jess open up about her personal journey working with global corporate giants below.
Before the Fairy BOSSmother
Jess came in with a résumé that most marketers would sell a kidney for. Adidas. Microsoft. Nestlé. Global agencies. Big budgets. Big rooms. She was shaping communication strategies back when “going viral” meant catching the flu.
But Jess had a problem she couldn’t see: her brand was split.
On one hand, she wanted to work with high-level executives. But on the other hand, she was still speaking to small business owners who almost never had the budget to work with her. These are two audiences with two completely different worlds, needs, and value ladders, and Jes was trying to serve both without fully committing to either.
The result?
Her communication was lukewarm, her positioning was vague, and her own story (the Adidas era, the billion-dollar brand experience) wasn’t being used effectively. She has a business called Copilot, but she wasn’t positioning herself as the woman who sits in the cockpit with CEOs, she was sitting in coach with everyone else.
Her biggest blindspot was that she still saw herself as “useful” when she should be “untouchable.”
During the show
This episode was all about forcing Jess to see herself the way the world sees her, not the way she watered herself down. I dug into her corporate career, her leadership experience, her marketing intelligence, and finally her global perspective. And the level of skill it takes to create campaigns for companies that operate in every time zone.
I asked her one question that cracked everything open:
“Why are you acting like you’re staff when you’ve already been the strategist CEOs rely on?”
You could see it hit, the shift, and the realization. This was the identity she had outgrown, but she couldn’t exactly figure out what that was, until now.
Together, we rebuilt her positioning:
✓ Jess isn’t a consultant - she’s the Copilot.
✓ She co-leads with executives.
✓ She operates at the top of the room, not the bottom.
✓ She brings her global legacy INTO her personal brand.
And most importantly, she no longer tries to speak to everyone. Her voice goes upmarket from now on.
This is the first time Jess admitted she wants more, a seasonal lifestyle, international living, and a brand sophisticated enough to sustain that. But to get there, she must finally own what she brings to the table.
After the show
Jess left the show with a completely new standard for herself. She’s restructuring her offers, repositioning Copilot into a top-tier executive service, reintroducing herself with her actual résumé, dropping the watered-down messaging, AND elevating her brand for the rooms she belongs in.
And most importantly? She’s finally stepping into the identity she’s earned. This episode was truly about unlocking the woman she had been hiding behind her own professionalism. Jess has the experience, the credibility, and now she has the positioning. This is the version of her that walked out of my studio is the one C-suite leaders will actually follow.
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