Jackie Pfeifer

OST Media Group

Jac Pfeifer has spent twenty years as a Head of / Lead of People and Business Operations, building and scaling companies and sitting in the rooms where the real calls get made: who to hire, what to pay, when to let someone go, and how to build your culture with intention.

Now she brings that judgment to founders. She helps online business owners with growing teams build the people side of their company: hiring and firing done with poise and empathy, aligned roles and responsibilities, pay decisions, performance conversations, and the light-touch guidelines that protect a business without burying it in policy.

Founders come to her asking, "What am I not thinking about?" Founders tell their friends, "Ask Jackie first." She's here to answer the questions before those questions cost them.

Off the org chart, Jac hosts On Second Thought, a podcast and newsletter (Pretty Big Thoughts) for accomplished women who are changing their minds and asking harder questions in order to live a fulfilled life that feels true to them.

She is also launching a community space on Substack for women coming into themselves through self-expression: style, beauty, fashion, and taste.

Small Business Grants for Women in September 2026

Discover September grants that can help women founders and solopreneurs fund Q4 year-end priorities.

Grants
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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.

Grants
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Grants
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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.

Finance
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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.

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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.

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What Founders Really Pay Themselves at Every Stage

A transparent look at founder compensation and how it actually evolves as your business grows.

Finance
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Grants
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Grants
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Finance
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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.

Community
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Grants
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Business Strategy
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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.

Business Strategy
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Grants
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Grants
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Business Strategy
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Grants
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Grants
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Marketing
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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.

Life & Wellness
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