Jessica Dragan
Business, accountability and burnout coach in Wisconsin
| Hourly rate range | $150 to $250 an hour |
|---|---|
| Focus areas | |
| Works with | Founders and business owners and Veterans |
| Also coaches | Life coach and Health coach |
| Based in | Wisconsin, United States |
| Credentials | EPIC 2020 |
Jessica Dragan is a business, accountability and burnout coach in Wisconsin. She helps owners plan how to exit their business with the value they want. She started her first business in Los Angeles in 2004 and later grew a company to 31 staff with branches in three states. She also spent 4 years in US Army transportation management and ran a mobile massage service business for over 18 years.
What Jessica helps with
Jessica works with business owners on building value and planning a strong exit. She also coaches on accountability and burnout.
- Exiting a business with the value you want
- Creative approaches to exit planning
- Growing a business from one person to a team
- Running a business through a crisis
- Improving staffing and customer experience
- Investment and retirement planning for owners
- Burnout and accountability
Who Jessica works with
Jessica works with business owners, investors and managers. Her listed areas include real estate, entertainment, sports, country clubs and financial planning. She also lists veterans as a group she serves.
Background and qualifications
Jessica entered business in 2004 when she became a sole proprietor in Los Angeles. She handled everything herself, from logos and SEO marketing to customer service and financing. She moved the business to Milwaukee five years later and hired her first employee in 2017. By 2019 she had 31 staff and branches in Illinois, Washington and Maryland. After the pandemic hit her business, she managed a mini-golf center for 2 seasons. It won a Best of Milwaukee award. She also worked 4 years in transportation management for the US Army.
Jessica Dragan pricing
Jessica Dragan reviews
The CoachVouch take
She has built a business from a solo start to 31 staff, then turned around a mini-golf center that won a Best of Milwaukee award.
Best for business owners who want to exit with strong value and plan their retirement.
Common questions
How much does Jessica Dragan charge?
Coaches like Jessica Dragan typically charge $150 to $250 an hour.
What does Jessica Dragan help with?
Jessica Dragan helps with exiting a business with the value you want, creative approaches to exit planning, growing a business from one person to a team and running a business through a crisis.
Does Jessica Dragan have reviews?
Jessica Dragan has no reviews on CoachVouch yet.
Is Jessica Dragan certified?
Jessica Dragan lists: EPIC 2020.
How do I contact Jessica Dragan?
Request an intro on this page. It's free, and we'll connect you with Jessica and, if you want, 2 or 3 similar coaches to compare.
Similar coaches to compare
Tick "Compare" on any coach to add them to your intro request.
John Haney
John Haney is a business coach and Certified EOS Implementer who works with growth-focused entrepreneurs and their leadership teams. He has led 400+ sessions with 70+ high-growth teams. Before coaching, he was a commercial real estate investor with multiple 7 to 8 figure exits, and a combat fighter pilot. More than a dozen of his clients have sold their business. He serves clients in Charlotte, Spartanburg and Greenville.
Richard Drake II
Richard Drake II is an EOS Implementer who helps business owners and their leadership teams. He is a former Navy pilot and aircraft commander. He spent 27 years in real estate and started four successful businesses. He was the owner and CEO of Renters Warehouse Houston, a three-time Inc. 5000 winner, and later sold it. He works from the Manvel and Katy, Texas area.
Deb Venable
Deb Venable is a Certified EOS Implementer who helps entrepreneurs and leadership teams solve root problems and lead better. She ran her own business for more than 30 years and used EOS to grow it before she exited in 2019. She is a past president of EO Chicago and has been in the Entrepreneurs Organization for over 20 years. Since her exit, she has written sales playbooks and coached management teams.
Josh Kosnick
Josh Kosnick is a business mentor and EOS Implementer in Madison, Wisconsin. He helps business owners and leaders line up their vision with daily execution. He founded Kairos Coaching and has built and exited three businesses himself. He also wrote The Kairos Code. His work mixes the EOS system with faith and a sense of purpose, so companies can be profitable and mission driven.
Browse related
Last updated September 2026. Request a correction.