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.
Start a conversation →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.
Resume review & LinkedIn refinement, interview prep, and general career coaching — the edge over an AI bot is judgment.
Learn more →Interview training, onboarding, and team-building workshops that bring groups along and make them stick.
Learn more →Ongoing 1:1 coaching to build self-awareness, navigate hard decisions, and realize your ambitions.
Learn more →Helping small teams build their people & talent strategy — from first hire to handbooks, policies, and a cohesive inclusion plan.
Learn more →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.
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.