Security Staff Acquisition & Development

Former Datto, Autotask SVP Len DiCostanzo Mulls Next Moves

Datto and Len DiCostanzo have parted ways, the long-time Autotask veteran and Datto have confirmed to ChannelE2E.

Len DiCostanzo
LinkedIn: Len DiCostanzo

DiCostanzo's journey in the IT services market extends back to 1984 or so, when he founded Turnkey Computer Systems -- a business technology consulting firm serving the New York metro area. That business, which DiCostanzo sold around 2002, generated about 75 percent of its revenues from services. Moreover, 50 percent of the company's revenues were recurring -- an impressive stat, considering the MSP industry was at its infancy stage.

DiCostanzo went on to consult for Kaseya before joining Autotask around 2008. While there, he led the company's channel development and partner program efforts, educating Autotask's ecosystem of MSPs and then continuing in that role when Datto acquired Autotask in late 2017. His tour of duty spanned multiple M&A deals, and Autotask's expansion beyond PSA (professional services automation) into RMM (remote monitoring and management) and file sync and sharing software.

Fast forward to present day. DiCostanzo and Datto have parted ways. Datto says his role will be absorbed by current team members. DiCostanzo, meanwhile, has several potential next moves on his white board.

Len DiCostanzo Looks Back, And Ahead

ChannelE2E caught up with DiCostanzo over email to recap his career journey so far, and to explore what might be next for the MSP-centric business and technology executive.

ChannelE2E: First, let’s look back: How did you first connect with Autotask?

DiCostanzo: I founded a business technology consulting firm out of college, writing custom applications for the first PCs and networks, evolving into a one-stop shop providing complete business technology solutions to SMBs and corporate departments. We built one of the first recurring revenue models in the late 90’s pre-managed services, and were acquired by a publicly traded company in 2002.  That part of my career gave me a solid technical and business knowledgebase that has served me well ever since, particularly around evolving from a break / fix project-oriented tech firm, to one with a recurring revenue stream from managed and cloud services. 

My next big thing was building a consulting business focused on helping vendors build their partner programs and channel sales efforts across multiple routes to market, including reseller networks and distribution. At the same time, I was also consulting with all forms of technology service providers on how to build a recurring revenue stream for their business around cloud and managed services. That work led me to Autotask. I was doing a keynote for a vendor client titled 'Top 10 Considerations for Building a Managed Services Practice’ at an industry event. Autotask’s CEO at the time was in the audience. He brought me in to do a small project for Autotask, and then bought me on full time in January of 2008 to bring IT DNA, or domain expertise, into Autotask.

ChannelE2E: Was there a highlight – a single greatest moment – from your Autotask and Datto journey?

DiCostanzo: There have been so many great moments at Autotask, so it is hard to single any one out. We grew our partner community 5x, built a partner program and channel sales effort from the ground up, and went from around 100 employees to 500. We built Autotask Community Live into one of the industry’s must attend events, and our global partner community was second to none. We built an incredible open ecosystem of vendors, partners, customers and channel stakeholders. And our products were world class and always got better. 

DiCostanzo addresses Autotask Community Live audience

If I were to single out a single greatest moment, it would probably be the first time we were acquired. After relocating my family to the Albany Capital District from New York City and embarking on 7+ years of long hours working with some of the best minds in the industry like Mark Cattini, Kevin Donovan, Scott Opiela, Moshe, Jake, Gary and a host of others, tons of travel and time away from the family, many ups and downs, the acquisition made the it all worth it. To see we were able to build something as successful as Autotask was gratifying in many ways. And it was not that it ended, as we then went on another run up until being acquired a second time and being merged with Datto last year. No doubt it was a great run, working for two great companies that are icons and titans in our industry, Autotask and Datto.

ChannelE2E: What do you want to potentially do next? Is there one particular thing – or multiple things?

DiCostanzo: Right now, I am focused a few consulting projects I have on my plate. With the experience gained from my time with Autotask and Datto combined with my MSP background, I feel I bring a unique perspective to clients I work with, whether they are vendors or MSPs. I can help vendors build their MSP/reseller channel sales effort, expand strategic alliances and integrations, improve partner success programs and more. For MSPs, I can help them build a better business with the knowledge gained from my own experiences growing and selling my MSP, and from working with many of the top MSPs in the world and understanding what makes them successful. 

I do feel my consulting efforts will lead me to my ultimate destination, as it helped me get to Autotask, so I am going to enjoy the ride. It could be landing with a vendor in a similar stage as Autotask when I first joined, looking to grow their channel business and build shareholder value, or running another MSP. I could also just stick to my consulting business, and develop an MSP Toolkit site I have been thinking about. More on that in the future….

ChannelE2E: Do you plan to take any time off? If so, any hobbies or catch-up items you’ll pursue?

Len and son Brandon DiCostanzo

DiCostanzo: I never took many days off at Autotask/Datto, so I will fit in some days off and travel where I can. I did just visit Italy for the first time, which is hard to believe considering all the work and other travel I do, and it was fantastic to visit Rome and see the sights. I will surely take another trip or two after that experience. I am definitely looking forward to hanging with my son Brandon, who is attending Bentley University outside of Boston, when he has the time for me (lol), as well as doing some skiing, working out and keeping my racquetball game strong.  But I won’t be off for long as I want to keep on going, helping the channel and making an impact where I can. 

Got a business or personal story to share within the IT channel? Email me ([email protected]) and perhaps we’ll share details in our ongoing Channel People coverage.

Joe Panettieri

Joe Panettieri is co-founder & editorial director of MSSP Alert and ChannelE2E, the two leading news & analysis sites for managed service providers in the cybersecurity market.