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.

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.

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    Steven B Harper:

    Lenny is a class act… any company would be lucky to have him as their channel chief. He has energy and passion that is unequalled in today’s workplace. Experience, Personality, Intelligence, and loyalty are all packaged in this man. I wish him well and glad this industry continues to benefit from his participation.

    Joe Panettieri:

    Hey Steven: Thanks for your readership and perspective. And thanks, of course, to Len for sharing some background on his personal journey.

    Brian Sherman:

    Best wishes, Len! I remember thinking how the sky was the limit the day you joined the Autotask team. Congratulations and good luck in your next adventure!

    Richard Tubb:

    A great read on a fabulous bloke – thanks Joe.

    Best of luck for the future, Len. You’re a top man, hugely respected, with a ton of valuable experience – and I’m excited to see what you achieve next in our industry!

    Evan Leonard:

    Lenny has always been great to me and my company CHIPS. I met Lenny at the New York VTN when he owned Turnkey. He was the VTN president and he could not have been a better mentor that was almost 20 years ago. Best of luck my friend and stay in touch.

    Miguel Zamarripa:

    Len is class act – a Channel legend, well loved and respected by all. There is nobody in the Channel with a larger fan base. Len has bestowed a great amount of wisdom on many of us MSP folk and has been the mastermind behind many successful partnerships. I’m sure he will continue that legacy and do great things. Well wishes on your next adventure Len!

    Frank Vitagliano:

    Lenny has had a fabulous career. I met him when he was on the VTN Advisory Council for Ingram and we became great friends. He has done an outstanding job utilizing his experience as one of the first MSP pioneers to his last role as vendor channel chief. Not easy to do, but through a combination of expertise and great relationship building skills he pulled it off. I am not sure what he is planning to do next but I know he will be a huge asset to any company that hires him.

    Luis Garcia:

    It’s going to be hard not to see Len at the Autotask/DattoCon conferences as I’ve seen him every year there for the past decade. Speaking with him at this years past DattoCon I even found out our office is in his old stomping grounds in Clifton, NJ back in his consulting days. Wherever Len goes they will have a priceless asset. GodSpeed Lenny!

    Frank Ballatore:

    Best wishes, Len. Hope to see you soon!

    Len DiCostanzo:

    I appreciate the kind words from everyone. You are all the best of the best and I am happy to have worked with you through the years. And I am looking forward to seeing all on the road in the near future! Peace!

    John Rice:

    Len, good luck moving forward. I have always enjoyed both working and playing with you over our careers. Perhaps we will get another chance to work together in the future. You have had a big impact on the industry and the people who work in it. You should be proud of your accomplishments. Looking forward to catching up with you soon.

    Alan Weinberger:

    All the over 1,500 ASCII members throughout Canada and the United States and ASCII’s staff , many who have met Len personally at our Summits wish him all the best on his new endeavors. I , Jerry Joutavas a d Shannon Mayer personally have spent many hours talking about the channel and have great memories.

    Jay McBain:

    Every year when I created the Top 100 most visible and respected people in the MSP channel list, Len was always near the top. It is hard to find someone in this industry who doesn’t know Len or who doesn’t have a story of how he has helped them.

    Joe, too soon to submit E2E Hall of Fame nomination?

    Michelle Ragusa-McBain:

    Congratulations on a phenomenal career and a wealth of accomplishments Lenny. Wishing you the best of luck in your continued journey. Definitely enjoy traveling, and bring your college boy Brandon food or money and he will welcome you with open arms 😉

    Joe Panettieri:

    E2E Hall of Fame — That wing of the building awaits fundraising 😉


    Jay McBain:

    Oh well, at least someone locked him in the NOC years ago – although that page seems to be a broken link today.

    Jeff Newman:

    Lenny! What a great journey. I’m so happy for your success and what the future holds. We had some great moments back in the day. Would love to hear from you.

    Jeff Newman

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