Ryan Weeks Is No Longer Datto’s CISO, Leaving Kaseya Channel With ‘Serious Concerns’

“Often I’ve been asked by channel CEOs, ‘How do we find someone like Ryan Weeks to lead our cyber initiatives?’ And usually I respond, ‘You don’t,’” says cybersecurity expert Wes Spencer.

Datto CISO Ryan Weeks, lauded for building a cyber-defense system to protect MSPs that “rivaled anything a large bank could muster,” is no longer in the role, two Kaseya employees told CRN.

Weeks’ departure from the Datto CISO role was communicated Monday to some employees at a short “off the cuff” meeting, during which attendees were told, “Ryan isn’t coming back. He is an advisor now, but he is off the day to day,” according to one source’s account of the conversation. Weeks had been on leave from Kaseya and was expected to return about two weeks ago but extended his leave, the source said.

Another source described Weeks’ new position as an “advisory role for members of the executive team.”

The sources spoke to CRN on condition of anonymity so as not to jeopardize their employment.

A Kaseya spokesperson offered no details on the role change.

[RELATED: ConnectWise CEO Jason Magee: Rob Rae Leaving Datto-Kaseya ‘An Opportunity’ For Us]

“I can confirm that Ryan Weeks is still an employee of Datto/Kaseya,” said the spokesperson via email, declining to make further comment when asked to verify Weeks’ current role. The spokesperson noted Jason Manar is currently Kaseya’s CISO but declined to make him or Kaseya CEO Fred Voccola available for an interview to discuss the company’s commitment to security.

Weeks could not be reached for comment.

In a June interview with CRN after Kaseya closed its $6.2 billion acquisition of Datto, Voccola said that Weeks would continue in his role.

“He’s not going anywhere,” Voccola told CRN at the time. “We’re excited to have Ryan staying on board. You know, Datto’s commitment to security is second to none, and we’re looking forward to continuing [to have] Ryan in his position as the CISO of Datto.”

Solution Providers Express Concern

Weeks’ departure from the Datto CISO role disappointed some solution providers.

“It’s quite the blow, as Ryan Weeks is well-respected regarding his serious approach to the role and [was] someone who made partners generally comfortable that Datto was taking their security of tools and assets seriously,” said the CTO of a large MSP in the Western U.S. that uses Datto. “It’s disappointing but was also expected that this would happen once Kaseya came into the picture. I‘ve felt Ryan’s vision for how you approach security and [that of] the new ownership wouldn‘t align.”

Michael Cervino, vice president of operations at Radnor, Pa.-based MSP Circle Square Consulting, said he has “some serious concerns” going forward as a Datto partner.

“Kaseya’s track record on security is not the best, so it doesn’t make me feel good,” Cervino said of Weeks’ departure from the CISO role, referencing the ransomware attack that hit Kaseya in July 2021. “We’ll be re-evaluating our relationship with Datto and/or Kaseya as a whole.”

Jason Slagle, president of CNWR, an MSP in Toledo, Ohio, who is an outspoken MSP security advocate, said Weeks was well-respected in the channel.

“He was a good advocate for MSPs securing their own houses, and his work on stuff like The Cyber Call showed it,” Slagle said, referencing the weekly cybersecurity virtual event—hosted in part by TruMethods, a Kaseya company—where experts talk with MSPs and MSSPs about the latest security threats to the channel. Weeks appeared along with other security experts in discussions designed to help MSPs fight cybercrime.

One former Datto executive speaking on condition of anonymity, when told of Weeks’ departure from the CISO role, described him as “a total rockstar and one of the single best hires Datto ever made.”

What Weeks Brought To Datto

When Weeks joined Datto six years ago, he was among the first to recognize the significant threat solution providers faced as their businesses became the targets of ransomware gangs around the world, said cybersecurity expert Wes Spencer, who also appears on The Cyber Call.

“Often, I’ve been asked by channel CEOs, ‘How do we find someone like Ryan Weeks to lead our cyber initiatives?’ And usually I respond, ‘You don’t,’” said Spencer, co-founder and former CISO of Perch Security, former vice president and external CSO at Kaseya rival ConnectWise, and current vice president and channel chief of cyber insurance company FifthWall Solutions.

Years ago, he said, Datto was the only large MSP vendor that was willing to commit the immense resources to do cybersecurity right. Behind the scenes, it was Weeks’ “hauntingly rare” combination of security know-how and business leadership that made it work, Spencer said.

“They allowed Ryan to build his own program, and I can tell you, as a former banking executive, it rivaled anything a large bank could muster,” Spencer said. “Datto truly cared about cybersecurity. They weren’t perfect, but with Ryan at the helm, they set the standard for a mature cybersecurity program. Many other companies want the same results but aren’t willing to put in the effort. I have profound respect for Ryan and what he built at Datto. It will remain as the standard all other large MSP vendors should hope to meet.”

Post-Acquisition Executive Changes

Circle Square Consulting’s Cervino said Weeks’ role shift is also troubling because it follows so closely on the heels of the departure of Datto channel chief Rob Rae, who left his role as Datto’s senior vice president of business development in October and has yet to resurface in a new position.

Datto CFO John Abbot, a Naval Academy graduate who attended Harvard Business School, left in June following the acquisition, joining AI company Dataminr as its CFO on Nov. 17.

“You can’t have that many senior executives leaving,” Cervino said. “I don’t know what the play is here, but it’s not a good look. I had my doubts already, and this keeps confirming my doubts.”

His biggest concern is how Kaseya is making “changes way too quickly.”

Faith In Voccola

Heather Simek, vice president of RJ2 Technologies, a Schaumburg, Ill.-based MSP, said the changes are expected, and she believes it takes about six months “when you’re merging two big companies together like that for things to kind of shape out.”

As a longtime Datto partner, she was surprised not to be notified of Weeks’ role change. Nevertheless, she trusts Voccola’s vision and said her company has no plans to go elsewhere.

“Fred is not a stupid person,” she said. “He’s not in that position because he’s not a smart man. He’s obviously surrounding himself with people he feels are going to make him stronger as a leader and the company stronger. I’m sure it’s disheartening to him because he has relationships with the people that are leaving, but I don’t think that’s going to stop him from moving forward and moving the company forward with the vision that he has laid out.”

Simek said she can see the positives in the types of change Datto is going through now that it’s part of Kaseya.

“I’m not one of those people who are uncomfortable with change,” she said. “I’m not on the side of, ‘Oh my gosh, the world is falling apart.’ I’m on the side of, ‘OK, this is a change, and change is painful and uncomfortable, but typically with change comes excitement and a new set of eyes.’”