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Josh Ferry of CloudInsyte Tells Us How the Smart Vendor Marketplace has Been Matching Businesses with Service Providers

kokou adzo



Josh Ferry CloudInsyte

First of all, how are you and your family doing in these COVID-19 times?  

Josh Ferry: COVID-19 has undoubtedly caused some obstacles for us; however, we are healthy and happy. For that, I am incredibly grateful.  

Tell us about you, your career, how you founded CloudInsyte

Josh Ferry: I am originally from a town with a population of roughly 600 called Forestville, NY. About an hour south of Buffalo, NY. After moving around and changing schools a few times, I attended college in Boston and, shortly after graduation, began my career in New York City. When I had my internship with a start-up now known as OwnerIQ, I decided I wanted a career in sales because I wanted to make money and always knew I wanted to be an entrepreneur. 

I moved up the career ladder quickly, and within 4 years, I led a team of 8 in the New York market at an F500 telecom company. After that, I accepted a position running the east coast for a leading cloud provider, and then my last role in the enterprise space I ran the Americas for a software business out of the UK that we sold for $1.4B.

In the earlier years, I started my first company, PureEdge Technologies, with a friend of mine, Chris Casale. We moonlighted until we ran out of vacation and sick days, and he has been a full-time PureEdge employee ever since. We learned a lot about what to do and what not to do; however, we bootstrapped a multi-million dollar business. After 10 years in revenue strategy at enterprise tech firms, my colleagues and I began seeing a concerning trend where the data suggested we were losing more business to indecision than anything else. The number of deals lost to indecision had skyrocketed from roughly 10% to over 55% in 3 years and wasn’t a unique problem to any single market (cloud, cybersecurity, etc.). 

The problem we discovered was that the market had become flooded with options while responsibilities on IT’s plate increased, and 70% of IT teams were running under headcount. IT decision-makers were left with minimal time to conduct proper vendor due diligence, RFPs are ineffective, and a wrong decision could lead to crippling technical debt. We founded CloudInsyte to democratize expensive analyst data and make it easy for these IT decision-makers to conduct proper due-diligence backed by data. We also help them manage the procurement process and provide vendor management/auto benchmarking on the back-end. We get to help the IT teams without pressure, and we help the vendors by only bringing them qualified opportunities that all but wipe out losing to indecision.

How does CloudInsyte innovate?

Josh Ferry: We listen, we analyze, and we solve. We are a data-driven organization that is completely changing how businesses, big and small, make purchasing decisions in the tech space. We automate the vendor due-diligence process by democratizing expensive analyst data on vendors and building profiles on our customers, which allows the platform to understand their unique needs and preferences for their project. This allows the customer to understand the entire market and how it stacks up against their needs and preferences, helping them more intelligently chose which vendors they want to engage with. The platform shows them expected financial outcomes, terms they should request, and then manage the vendor agreements to automate the renewal and/or benchmarking process. The goal is to save them time & money while ensuring they feel safe with every procurement decision they make. We also offer inexpensive flat-rate pricing and month to month agreements or on a project by project basis.

How the coronavirus pandemic affects your business, and how are you coping? 

Josh Ferry: We’ve continued growing, and for that, one has to be happy. With that said, we grew slower than expected, had two large projects get delayed significantly, and we lost funding from an investor due to COVID-19. We also had the opportunity to help our amazing Western New York community, as well as many other townships and municipalities with free service from a number of top providers in unified communications and cloud, which was extremely rewarding to all of us at the company.

Did you have to make difficult choices, and what are the lessons learned? 

Josh Ferry: Like any business, we had to make difficult choices. We had to change course and adapt. We had the advantage of being a nimble start-up with an experienced team that understands adversity. They stepped up to overcome that adversity. I think the biggest lesson I learned was not to let go of my optimism. As a leader, I think your biggest fear is letting your team, your investors, and your customers down. The uncertainty weighed on me, regardless of the talent we had around the table. I just had to trust them and trust the product.

How do you deal with stress and anxiety? How do you project yourself and CloudInsyte in the future? 

Josh Ferry: At the beginning of COVID-19, I decided to reflect more on myself and work more on the long-term strategy of CloudInsyte. This led me to realize I was not making healthy decisions. I was not sleeping enough, drinking enough water, diet sucked, I wasn’t spending enough time with family, and exercise was far too infrequent. I was also focusing my emotions & time on things completely out of my control. The sun was still rising every day, and the problem we set out to solve still existed. So, I only focused on what I could control, which helped me with stress and anxiety.

Who are your competitors? And how do you plan to stay in the game? 

Josh Ferry: Our biggest competitors are companies who stay “status quo” with their RFP processes, consultants, or large analyst subscription services. Therefore, for us, it’s about continuing to iterate and keep solving problems for our customers and allow the data to speak for itself. That and I plan to trust the people I have around the table because it’s a special team, and we are lucky to have them.

Your final thoughts?

Josh Ferry: COVID-19 has devastating effects globally and hurts some worse than others; however, being an entrepreneur means never giving up. We work 80 hours a week to avoid working 40! Trust yourself, trust your team, and control what you can control… The rest is just noise. 

Your website?

Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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