DANIELLE WILKIE

I guide people and organizations through pivotal moments, bringing clarity to complexity and helping them build aligned next chapters.
Over 25 years, I’ve stepped into high-stakes situations including managing billion-dollar businesses, scaling marketing engines, and supporting leaders at crossroads. Today, I bring that same clarity, alignment, and momentum to your transition.
My Story
Helping professionals and organizations move through the in-between with alignment, clarity, and momentum.
I’ve spent my career turning uncertainty into strategy through the building and scaling of B2C and B2B businesses, I've launched new markets, led rapid expansions, built new business lines, and guided organizations through acquisitions and restructures.
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At Compass, I managed a $220M P&L, launched 10 new markets to the #1 brokerage position, built a national customer success function and created a new service business generating millions in annual revenue in just the first six months.
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At Craftsy, I led a $40M marketing operation, doubled eCommerce revenue, built a YouTube strategy with over 1M subscribers and drove a successful acquisition by NBCUniversal.
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At NetQuote, I let the revenue and product teams growing the business from $40M to over $100M and launched a new marketplace business from $3M to $48M in three years.
My work has always been about moving from uncertainty to aligned action - bringing clarity to chaos and translating vision into momentum.
Today, I bring that same skill to a different scale and with a more intentional lens. As a transition architect I help people and organizations build aligned next chapters - whether that’s a high-powered professional navigating what's next, a seasoned real estate leader building her coaching business, or an organization reimagining its future.
Through The Helm, The Midlife Sabbatical, 1:1 coaching, and strategic advising, I guide transitions with the clarity, alignment, and momentum that make lasting change possible.

Work With Me
Whether you’re an individual in transition or a company at an inflection point, my role is the same: bring clarity, alignment, and momentum to complex situations.
Writing
My writing is where I unpack the patterns I’ve seen in 25+ years of leading, building, and navigating change. It’s a mix of strategy and storytelling - designed to spark clarity, invite reflection, and help you move from uncertainty to aligned action.

New posts 1-2 times / week. You'll find me talking about:
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The changing landscape of residential real estate in the US
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Using AI at work and its broader implications
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Coaching as a practice and where it’s going
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My experience as an instructor at The University of Chicago
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What I’ve learned and experienced during my 25 year career across startups and Fortune 500 companies
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What a sabbatical is for business professionals and my experience with it
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My leadership journey as a woman
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What it’s like starting and bootstrapping your own business

4-6 new blog posts per month focused on:
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Conscious leadership
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The Helm Podcast guest insights
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Real estate industry strategy
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AI headlines relevant to RE
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RE Coach insights

I completed my own 6 month sabbatical in 2023 and found the resources - in one word - thin. Plenty for academics or religious leaders but very little for seasoned business professionals. I write about the experience here.
Podcasts
Whether it's notable women leaders in real estate or opportunities to talk about coaching and leadership, there's something to give you a taste of my POV.

Wisdom From The Helm Podcast
My co-host, Heather Frick, and I interview top women in real estate to get behind the "highlight reel" and hear what it takes to be successful in work and in life.
Podcast Guest Appearances
I've been grateful to share my story and insights on podcasts that explore self leadership, transition, being a woman in business and the gender gap in real estate coaching.

Manage Yourself First


Re-imagining RE Coaching

Women Who Lead
Empowering Women in Real Estate

Why Aren't There More Women in RE Coaching?

Creating a RE Coaching Revolution