Sheila O'Sullivan is a strategist, builder, and communication expert based in New York City. She is the founder of SOScreates and creator of the Communication Comfort Zones framework, a practical, research-backed approach to eliminating the communication style friction that slows down even the best teams. Her career started in finance (first a boutique law firm, then trading desks at Donaldson, Lufkin & Jenrette and Lehman Brothers) before having a pivotal realization that building things mattered more than financial upside alone. She left Wall Street to co-build Prime Advantage, a B2B group purchasing organization marketplace. The business survived the dot-com bust, a VC buyback, and the Great Recession before reaching an eight-figure exit to a strategic buyer. Today Sheila channels that operator experience into helping founders and leaders do the hard work of building without losing themselves, their teams, or their sense of humor. She teaches Communication Comfort Zones through live cohort courses on Maven, private workshops, and one-on-one engagements. She holds a BA from Georgetown University and an MBA in Finance from NYU Stern.
13 Grants for Women Founders to Apply for in August 2026
Explore grants for women founders accepting applications in August 2026, including the $5,000 Entreprenista Evolve Grant presented by IT Cosmetics.
How to Actually Read Your P&L (And What to Look For)
A practical guide to turning your profit and loss statement into a real decision-making tool.
What I'd Tell My Pre-Kids Founder Self About Scaling
Growth looks different on the other side of motherhood. These founders share what they wish they'd known earlier about scaling, sustainability, and the village that makes it all possible.
The Systems That Make My Business Work as a Mom
Forget hustle culture. These mom-founders built intentional systems like time-blocked calendars to outsourced meal prep, that let them lead their businesses and show up for their families.
What Founders Really Pay Themselves at Every Stage
A transparent look at founder compensation and how it actually evolves as your business grows.
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5 Ways Community Can Be Your Greatest Visibility Strategy
Discover 5 ways community can become your most powerful visibility strategy and help women founders grow their brand, credibility, and opportunities.
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Why Your Personal Brand is Your Greatest Business Asset
Discover how personal branding can transform your business journey from Stephanie Cartin, co-founder of Socialfly and Entreprenista.
The Decision I Would Undo If I Could
Staying invisible too long. Waiting for outside permission that was never coming. These founders share the decisions they'd undo and what finally changed because of them.
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Built Together: Mother-Daughter Duos Redefining What It Means to Scale a Business
These mother-daughter co-founder pairs are proof that some of the most powerful business partnerships start at the kitchen table.