Jessie Ott

Commander
DISC Type : D

CEO & Founder at CrossRoads Solutions

Dallas, Texas, United States

Overview

Jessie Ott is the CEO and Founder of CrossRoads Solutions, where she helps CPG companies turn data into decisions. With over 20 years of experience in the wine and spirits industry, she is a passionate problem-solver and brand builder, holding a WSET Level 3 certification and an MA from Rennes School of Business.

Outside of her CEO role, Jessie is deeply immersed in the beverage world as the host of the "Thirsty Thursdays @3PM EST" podcast, exploring industry innovation. She has been recognized as a "fabulous entrepreneur" and founded the North Dallas chapter of Lean In, showing a commitment to community leadership.

She is a 20+ year veteran in the highly competitive wine and spirits industry who has successfully transitioned into a tech CEO role.

Personality Overview

Strong-Willed

Impact-Driven

Candid & Clear

They like to be in a position where they can control the conversation and terms.  More than the product, they care about the effectiveness of the product. They respond well to strong and respectful communication.

Topics They Care About

CPG Data Analytics
Her company, CrossRoads Solutions, focuses on unifying sales, marketing, and inventory data to provide CPG brands with actionable, real-time insights for growth.
Beverage Industry Innovation
As host of the "Thirsty Thursdays" podcast and a 20-year industry veteran, she frequently interviews founders and discusses emerging trends, from new products to technology.
Entrepreneurship
She has founded multiple ventures, including CrossRoads Solutions and f n b Innovation, and participated in the Techstars Tulsa accelerator with a previous startup.

Media Appearances

Reframing Data Accessibility for Growing Businesses – Jessie Ott, CEO & Founder of CrossRoads Solutions. Featured in Woman's World

See Now

Work History

1-2025
CEO & Founder at CrossRoads Solutions
1-2025
Managing Partner at Specialty Brands Wines & Spirits
3-2023
Owner at f n b Innovation
1-2023
Podcast Host at Thirsty Thursdays @3PM EST
10-2022 - 3-2023
Co-Founder at KÉXY at KÉXY

Education

1999 - 2000
MA from Rennes School of Business
1997 - 1999
BA from University of Northern Iowa

More Information

Social Presence :

Prographics :

Exp : 25 Location : Dallas, Texas, United States Job Level : Leadership Designation : CEO & Founder at CrossRoads Solutions
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Insights For Selling To Jessie

During A Call Or A Meeting

DO's

  • Help them weigh the risks by sharing objective proof points without becoming too analytical
  • Be respectful but crisp
  • Speak about competitive differentiation that your product offers

DONT's

  • Do not spend too much time focusing on product tech or features
  • Avoid being too verbose
  • Do not hesitate from asking counter questions, just avoid challenging their authority

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jessie is

  • Confidence in impact is paramount to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Jessie

  • If they decide not to go ahead, they will say no without hesitation.

Insights For Deal Planning

    How fast (or slow) will Jessie move?

  • They can take decisions very fast if you manage to convince them.
  • Can Jessie take some risk or not?

  • The risks don’t matter much to them.

You And Jessie

Personality Compatibility


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