Leadership Team


Matthew Taylor

Chief Executive Officer

After a career in equity and venture investing, Matthew joined WIN in 2019 to help the company prepare for the coming telecommunications transformation.  Prior to WIN, he co-founded Gypsum Ridge Capital, a private investment firm focused on small business technology.  His prior experience also includes Stratfor Global Intelligence and Control Risks Group, both geopolitical risk-focused consultancies. He also served for 10 years in the United States Marine Corps.

Outside of WIN, he stays involved in the Chicago venture capital and veteran communities, promoting growth in small companies.  He is an active pilot, skydiver, and BASE jumper.

Matthew holds an MBA from the University of Chicago Booth School of Business, an MS in Finance from Southern Methodist University, and a BA in Political Science from Indiana University.

Andrew Maier

President & COO

Andrew has been with WIN for over 19 years and has held multiple positions including engineering, manufacturing, and operations which has given him a unique perspective on all aspects of the company. His current role as President focuses on the business operational leadership side of the company. At WIN, our passion is providing connectivity options to our customers that allows the benefits of wireless technology to help continue to grow their perspective businesses.

An avid music, food, and sports fan, also volunteers his time as a youth basketball coach.

Andrew holds a BS in History from Eastern Illinois University with a concentration in cultural geography. He also holds certifications in improving business and finance operations from the University of Illinois at Urbana-Champaign and has published various industry articles.

Mike Ward

Chief Revenue Officer

Mike joined WIN Connectivity as Chief Revenue Officer responsible for building-out the Sales Organization and executing on the expanded WIN Go-To-Market strategy. He has 25+ years of experience in telecom building, optimizing and leading successful global sales organizations in high-growth technology companies. With extensive experience in early-stage, turnaround and market established companies, he has built world-class sales teams and led companies such as Dialogic, Edgewater Networks, MetaSwitch, Paradyne Networks, Ascend Communications and Lucent Technologies to increased, profitable revenue growth leading to desired capital exits.

Mike serves on the Board of TUF Life Skills, a growing cloud-based Social & Emotional learning platform that provides engaging, interactive digital courses using powerful testimonials from celebrity athletes to inspire and teach kids the valuable life skills needed to succeed.

Mike holds a BS in Electrical Engineering from Virginia Tech and an MS in Management from the University of South Florida.

Tim Dentry

Chief Technology Officer

Tim joins WIN Connectivity as the Chief Technology Officer, bringing 20+ years of technology experience in a variety of technology sectors. Tim has worked in various engineering, design and support roles with technology ranging from carrier-class networking equipment, enterprise and data center, health care IT, cybersecurity and real estate. Tim has worked in both established communications companies such as MCI and Lucent and has also been a part of early-stage startups such as Edgewater Networks, taking products from the design phase all the way to implementation and ongoing lifecycle management. Tim provides support for the broader WIN team by focusing on key areas such as technology evolution, product development and design, as well as OSS/BSS and back-office solutions. Tim brings to WIN the experience of leveraging cloud infrastructure to deploy WIN’s technology solutions and is responsible for the lifecycle support of all of WIN’s technology offerings including Connectivity-as-a-Service. Tim is proud to have served in the Marine Corps for fourteen years, in various unit leadership and operational planning roles, and is a graduate of Texas A&M University in College Station, Texas.

Jamaal Smith

VP, East Region

Jamaal brings over 20 years of experience working in the telecom industry. His responsibilities at WIN include new business development and sales to key verticals including commercial real estate, hospitality, education and healthcare. Jamaal comes to WIN most recently from Vision Technologies in which he was a National Account Manager focused on growing Vision’s national footprint of wireless deployments. Prior to that, Jamaal held management positions with Boingo and Verizon.

When Jamaal is not working, he enjoys spending time with his children and extended family as he has been an AAU coach for the past 20 years and enjoys giving back to the youth in his community.

Jamaal is also a board member of Man-2-Man which is a youth mentoring program in Maryland that provides guidance and direction to underachieving young men and women.

Eric Isherwood

VP, Central Region

Eric has been working in telecom for over 20 years in a variety of roles. His responsibilities at WIN include new business development and sales to key verticals including commercial real estate, hospitality and healthcare. Eric comes to WIN most recently from ExteNet Systems, where he helped to grow and further establish the wireless in-building and converged network services businesses. Prior to that he held management positions with Boingo, Cingular Wireless (AT&T), Motorola, and Nextel.

Eric holds a Bachelors Degree in Marketing from Bowling Green State University.

Glen Baxley

VP, Carrier Relations & West Region

Glen has over 27 years of experience in the telecommunications industry. At WIN, Glen is responsible for working with Venue Owners and the Tier 1 Wireless Carriers to ensure WIN’s network solutions meet both the property owners and each carrier’s needs. Prior to joining WIN, he was Sr. Vice President on the four-person founding team for Connectivity Wireless Solutions 3rd Party Neutral Host subsidiary Simplifi Wireless Group, LLC. He has also worked for Mobilitie, Mycom Network Services, Nortel/Ericsson and MCI. During has career Glen has held various leadership positions in the Wireless Industry including, Sales, Business Development, Engineering and Project Management. Some of the key projects he has been part of during his wireless career include; the initial deployment of the Verizon Wireless LTE network, the rip and replace of AirTouch’s AMPS/CDMA wireless networks in Southern California, Las Vegas, Georgia and Michigan, and the initial network build out of the Sprint PCS CDMA network. Prior to his career in wireless telecommunications, Glen served 9 years in the U. S. Marine Corps. Glen holds a Bachelor of Science Degree in Electrical Engineering from Texas A&M University.