People work, done with care and a point of view.

I'm Maggie — a talent and people leader turned independent advisor. After 17 years inside tech, I help individuals navigate their careers and help founders build teams consciously, equitably, and with a real plan. Human judgment, not a bot.

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Services

For the person and for the team.

I work with two kinds of clients: individuals navigating a career move — often PMs and others in tech, whether recently laid off or quietly weighing what's next — and teams building their people function from the ground up. Different work, same foundation: clarity, equity, and follow-through.

About me

Seventeen years inside the rooms where careers are made.

I'm Maggie Wynn, founder of Magnolia Strategy Group. I spent most of my career leading talent acquisition and people strategy in tech — most recently as Head of Inclusion & Impact at Squarespace, and before that in senior recruiting roles there and at Dropbox. I'm known in my circles as a talent expert for Product and hiring.

I've sat on every side of the table: screening and hiring, coaching leaders, building equitable processes, and helping people through the messy, high-stakes moments of their working lives. What I love most is helping individuals move their careers forward and helping teams realize their ambitions.

My approach starts with empathy and leans on radical candor — I'll see the best in you and give you a realistic view of what's possible, then help you get there. My background is in sociology and women's studies, and that lens still shapes how I think about fairness and systems. I'm currently pursuing an ICF coaching credential to deepen the practice.

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Let's figure out what you need.

Tell me a little about where you are and what you're working toward. First conversations are free, and there's no pressure to commit to anything.

Thanks — I'll be in touch soon.