Contributors

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Host

Carrie Richardson

Carrie Richardson is a partner at Fox and Crow Group, a firm specializing in strategic growth and exit planning for small and medium-sized businesses. 

As the host of the WIN podcast, Carrie interviews successful entrepreneurs and business leaders from various industries.

Carrie has been instrumental in helping numerous businesses scale and achieve their full potential.  

Carrie's entrepreneurial journey began with her own ventures, which she successfully scaled and exited, providing her with firsthand experience in the challenges and triumphs of business ownership. 

Carrie is dedicated to fostering a community of like-minded entrepreneurs and continuously seeks to empower others through education and mentorship. She is an author and frequent speaker at technology industry conferences and events.

Book Carrie on your podcast:  https://randr.consulting/connect


https://linkedin.com/in/carrielynnrichardson
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Co-host

Ian Richardson

Ian Richardson is  the visionary founder of Fox and Crow Group, a consultancy specializing in strategic growth and exit planning for small and mid-sized businesses. 

As the co-host of the WIN podcast, Ian provides listeners with invaluable insights into the world of business strategy and entrepreneurship.

With over two decades of experience in the business world, Ian has a proven track record of helping companies navigate complex challenges and achieve remarkable growth. His strategic approach and deep understanding of market dynamics have made him a sought-after advisor for businesses looking to scale and optimize their operations.

Ian's entrepreneurial journey is marked by a series of successful ventures. He has earned him a reputation as a forward-thinking and innovative business leader.


Ian holds a BBA from Northwood University, and is a frequent speaker at industry events.

http://linkedin.com/in/ianalexanderrichardson

Guests

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Guest

Andrew Moore

As the President of Ridgeview Advisors, Andrew is focused on helping Managed Service Providers (MSPs) operationalize trust. With over 25 years of experience in the IT industry, he understands the intricacies of scaling MSP businesses, improving operational efficiencies, and building lasting relationships between MSPs, clients, and investors. 

Ridgeview Advisors exists to help MSPs not only grow but also to create systems that ensure consistency, transparency, and above all, trust—from sales through service execution.

His background includes the development of solid operational systems and processes that allow MSPs to build lasting value for their clients and investors alike. Andrew believes that building trust starts at the sales process, is reinforced through marketing, and must be carried out in every touchpoint of service execution.


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Guest

John Ahlberg

John Ahlberg is the CEO and founder of Chicago-based Waident Technology Services.

Waident is a Chicago-based SOC 2 cybersecurity and IT outsourcer that supports and manages SMB technology in Chicago, Milwaukee, and across the Midwest. We help organizations keep their people productive, their enterprise running, and their company data safe.

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Guest

Rob Senatore

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Guest

Robb Rogers

Robb Rogers is the CEO and co-founder of OSR Manage, where he specializes in sales management, sales training, and B2B sales processes. He has extensive experience in sales leadership, with over 19 years of experience across various industries, including pharmaceuticals, automotive, and managed services. 


OSR Manage, co-founded by Robb, focuses on providing sales and account management solutions for MSPs. The company helps MSPs overcome common sales challenges and grow through a structured program designed to address each stage of business growth.

For more information, you can visit Sales MaturIT or view their various resources, including podcasts and industry discussions.