On this episode of Adapt or Die: Transformative Leadership Conversations, former tech CEO-turned-executive coach Andreas Pettersson sits down with Alyssa Trenkamp, a fearless marketing executive who’s navigated five successful acquisitions in the high-growth B2B SaaS world. Now leading Americas Marketing for a global technology company, Alyssa shares how a chaotic startup office, a loyal CEO, and one mantra from her mom—“Make it a great day”—shaped her career path. From being blindsided by team drama to learning how to self-coach through self-doubt, Alyssa offers a masterclass in resilience, allyship, and redefining success through the “meaningful middle.”

Challenge →
Facing mutiny from her team and an offer letter on her desk, Alyssa sat across from her CEO—knowing the next few minutes could define her career. Her team’s grievances threatened everything she’d built, and walking away would’ve been easy.

Adaptation →
She leaned into honesty, ownership, and a deep relationship with her CEO—who saw the situation for what it was and had her back. That choice cemented her conviction to lead, not leave, and reinforced her belief that true growth means not running from the fire—but through it.

Success →
With unshakable confidence and a knack for finding “the meaningful middle,” Alyssa’s built lasting teams, driven massive growth, and earned the kind of trust that turns colleagues into repeat partners across companies. She’s now writing a book chronicling her hard-won lessons—straight from the heart of startup chaos.

🔥 60-Second Hot Seat:
She broke the “be nice and conform” rule, let work friendships go deep, and rebuilt confidence by listening to her own voice—literally. (Yes, she records her own book for pep talks.) Her mantra? Don’t lead from fear. Remember who you are—and then take the next step.

Startup chaos. Female allyship. Inner critic management. Alyssa’s story is fuel for any leader ready to lead boldly, without asking for permission.

📘 Power Without Permission
Akyssa is a co-author in Power Without Permission. Get your copy at leadersadapt.com/book and join the community of women building unapologetic leadership from the inside out.

Visit www.leadersadapt.com/adaptordie for show notes, free resources, and coaching programs.

Listen to more episodes on Mission Matters:
https://missionmatters.com/author/andreas-pettersson