Episode 27

Robert Cioffi, Progressive Computing “No Man is an Island”


Robert Cioffi Progressive Computing
Managed Sales Pros

Robert believes that success of your business and what can drive growth can be learned when you open yourself up and be vulnerable.  While bravado and ego may lead people to launch an MSP, many do not let people in to offer suggestions, guidance, and assistance.


Robert is a strong proponent of peer groups and coaching as a key to bettering your business and you personally.  As such he is now a facilitator for IT Nation Evolve Peer Groups.

by | Oct 27, 2020 | Uncategorized


Brian Doyle

Tim McNeil

Robb Rogers


Robert Cioffi
Progressive Computing Group

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About This Episode

Robert Cioffi is COO & Co-Founder of Progressive Computing located in Yonkers, NY.  Launching in 1993 very early in his and his partner’s careers they learned a lot through the school of hard knocks.  One of the primary drivers of his company’s long-term success was engaging a coach and being part of a peer group.

Robert starts the conversation is it takes a certain mindset and ego to start a company, but that can also be one of the biggest blockers to growth.  Coaching helped him learn the things he didn’t know and start changing the business model, launching managed services in the early 00’s.

He speaks about his business model and how it differs from the average MSP.  Many speak of the “All you can eat (AYCE)” model, but Progressive has taken that to a very literal stance.  They include all projects within their plans. 

They view the relationship as a true partnership with their clients and truly have adopted and internal IT department mindset of we do what the client needs done, no questions asked. A true win-win proposition, eliminating project cost resistance and reduces the overall support cost to Progressive.

An EOS practitioner, Robert talks about how it has been a game changer for his company. This structure helped accelerate the growth of the company providing clarity to what it would take to get to the next step. 

Robert talks about the future of the cloud and cybersecurity within their business.  He expands on how Microsoft Teams has accelerated cloud use for clients and how the conversations around fully cloud solutions have increased.

We also speak about the M&A climate in the space and the ultimate plan for his organization in the long-term.

We have a deep discussion on how to be humble and embrace the guidance of those that have been there to support our journey.  Allowing yourself to be vulnerable and open can lead you to some of the best experience and lead you to some of the critical external input that you can leverage to grow.







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