top of page
Writer's pictureGreat Companies

Jennifer Hensley: Winner of the 2024 Great Companies International Women Entrepreneur Award


Name: Jennifer Hensley CLU, ChFC

Business Name: Playmaker Coaching and Consulting LLC

Location: Milwaukee, Wisconsin, USA

Establishment (Year): 2019

Category: Advertising & Marketing

Profession/ Specialty: Marketing

Social Media: Linkedin


Company Detail:

Running a small business takes a team and winning plays. Playmaker Coaching and Consulting LLC is here to help financial advisors, attorneys, and referral-based business owners play their position, stay on offense, and create a system to score more ideal clients and raving fans. They can be your teammate, coach, or the general manager.


Unique Selling Proposition or Competitive Advantage:

With over 20 years working with small business owners and a depth of experience in marketing, sales, operations, compliance, and leadership, Jennifer Hensley CLU, ChFC knows how things fit together. She can see the big picture and drive the steps needed to create a winning system for ongoing success. While other marketing firms typically just focus on digital or branding, at Playmaker Coaching and Consulting LLC, they take a comprehensive approach because they understand that your brand touches.


Challenges Faced During the Journey:

Becoming a business owner after 20 years in corporate raised the same concerns Jennifer's clients often have; how to prospect authentically, build a business around the things she does best, and impact more people through a system she could scale. She never saw herself as a business owner and always felt like a generalist so she had to discuss what separates her from others and ultimately do all the things she coached others about for herself.


Advice for Women Entrepreneurs:

Don't grow it alone. While you may be a solopreneur, there are so many resources and mentors that want to see you succeed. Ask for guidance, help, and feedback. Jennifer would also say to invest in people and experts over tools and technology to start.





bottom of page