Bob Matthews

Partner & Managing Director
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About Bob Matthews

Bob Matthews is an expert technology and communications advisor with more than 40 years of experience. As a Partner and Managing Director with UPSTACK, Bob focuses on sourcing creative network and technology solutions for existing and prospective customers.

Bob began his sales career in the early 80’s helping to launch the first Miami office for the telecommunications carrier SPRINT. Over the next several years, Bob’s sales expertise and prowess led to successful major account sales executive careers with companies, including ARGO, Microtel and ATC. From 1987 through 2001, Bob moved into a sales management role and led multiple successful teams that focused on major and national account sales in the southeast at several companies, including Metromedia, LDDS, WorldCom, MCI and C&W. During this time, Bob received numerous performance recognition awards as a Director of Sales.

In 2001, Bob partnered with David Weisenberg to form Progressive Communications Management (PCM). PCM advises enterprise and midmarket organizations on optimal cloud, networking and communications solutions to meet business and financial objectives, and backs up its recommendations with ongoing management and support. The company offers connectivity, managed network services, cybersecurity, Secure Access Service Edge (SASE) and SD-WAN, cloud infrastructure and applications, data center and colocation, and unified communications and contact center solutions. PCM is particularly known for its vast repository of expertise and industry contacts that it leverages to elevate clients and is consistently recognized as an industry top performer.

One of Bob’s most impactful and timely deployments was for a financial firm looking to replace their on-premises phone system and move to a cloud contact center environment. The team began the provider evaluations just before the initial onset of the COVID-19 pandemic. By taking the lead and project managing all aspects from supplier selection and contract negotiation through implementation and activation, Bob was able to complete the migration in sufficient time for the customer to temporarily close their call centers and allow their agents to work remotely. Beyond the ROI value in migrating to cloud contact center services, the customer’s business remained viable throughout the pandemic, with their head of IT stating “the speed to deploy, and successful launch of the contact center solution probably saved our business.”

Bob attended Ithaca College in New York where he earned a Bachelor of Science degree in finance. Now in Florida, Bob prefers spending his downtime with friends and family and enjoys traveling, attending sporting events and concerts, as well as an occasional round of golf.


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Unified Communications

Cloud Contact Center

Cloud Contact Center

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Network Connectivity

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Cloud Services

Recognition & Certifications

  • 8-Time Intelisys Presidents Club Winner
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Fort Lauderdale, FL