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Cultivate Advisors
Our Advisors

Jessica Osborn

Senior Business Advisor

New Orleans, LA

Jessica Osborn

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Wielding high doses of empathy and a knack for structure, Jessica Osborn is committed to helping owners create clarity in the chaos of running a business. Focused, effective and responsive, she aims to help ambitious owners achieve profit, productivity, and peace of mind. 

As the founder of a clothing design company for startups, Jessica advises with entrepreneurial experience. After growing her company to 12 employees, she flipped the model, created an online course for DIYers, and enhanced scalability. Jessica has a unique perspective on scaling a business. Before founding her own company, she worked as a versatile designer/marketer/salesperson for another startup that scaled to $15M during her five-year tenure at the company. 

Jessica Osborn
As a Cultivate Advisor, Jessica helps companies become better structured and more prepared for growth. She helps owners set goals, solve problems, and pivot when necessary. Her outside perspective and passion for entrepreneurship is evident and contagious. 
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Some of Jessica’s recent client success stories include figuring out the ideal team structure, hiring well, organizing finances, increasing productivity, and expanding reach within the correct target market. She excels at creative marketing, structuring for more owner freedom, and onboarding new employees in a way that propels them toward success. 

Advising with Cultivate has given Jessica the opportunity to affect a wide variety of businesses and industries. She finds her work fulfilling, never dull, and professionally sharpening. She loves knowing that as she helps owners succeed, this creates a ripple effect, which helps its employees and the broader community. 

A New Orleans native, Jessica is married with one daughter and has a huge extended family. Sand, sun, and watersports make her happy, and 15+ years as a yogi keeps her sane. Former president of the LSU wakeboarding team, an AirBnB host, and an avid adventurer, Jessica loves the kind of travel that puts her amongst the local people, flora & fauna.