Kaseya reaches a crossroads

Kaseya needs to execute in key areas to achieve its goals

Kaseya has several challenges ahead including:

• Appoint a new CEO who can achieve IPO readiness, gain Wall Street’s approval, and win over partners with industry credibility and community-focus.
• Better integrate the 40-plus products in the company’s portfolio to fully achieve its platform vision and scale that platform through infrastructure investment.
• Create a vision of Kaseya that incorporates AI, which will become a key component of the future MSP platform.
• Rebuild trust with partners by consistently executing on the new community focus signaled by executives during Kaseya Connect.

Forces in play at Kaseya Connect

Kaseya is at a pivotal moment. The RMM/PSA platform tools provider for MSPs is without a CEO for the first time in a decade. The fallout from Datto’s integration into Kaseya three years ago — and the cultural friction it caused for Datto-aligned partners — continues to impact perception among some in the ecosystem. The company has caused friction with partners in the wake of unforgiving billing issues and aggressive sales tactics, which have overshadowed efforts to build a stronger sense of community among MSP customers.

But while Kaseya may temporarily lack a top leader, it demonstrated during its Kaseya Connect event this month that it is far from rudderless. The absence of its longtime former CEO provided an opportunity for other key executives to move into the spotlight. Indeed, if any one of these executives had successfully navigated an IPO before, they may have been a natural successor to the CEO after his January departure. Without the IPO experience they remain solid leaders who can help a new CEO execute on many fronts. As one of these executives pointed out, many of these existing Kaseya leaders have MSP DNA — they are not private equity picks — they are actual MSPs who have joined Kaseya through hiring or acquisition.

Kaseya continues to capitalize on early successes of its “unit economics” plan of selling bundles of its core platform offerings for discounted prices. Kaseya introduced Kaseya 365 Pro a year ago — a basic bundle of MSP services including RMM, antivirus, EDR, MDR, patch management, ransomware rollback and endpoint backup at a US$5.25 per end point. This appears to be a successful strategy embraced by existing Kaseya partners and resulting in some competitive wins.

Some metrics Kaseya shared during Kaseya Connect:

• 7,000 partners now use Kaseya 365 Pro
• 3.7 million endpoints are now managed on Kaseya 365

The strategy was further reinforced by several key product announcements at Kaseya Connect. Each one aligned with broader company priorities, from deepening platform integration to simplifying pricing and elevating automation through AI. These announcements include:

• Kaseya SIEM: A fully managed cybersecurity solution built on RocketCyber and SaaS Alerts.
• Kaseya 365 Ops: A package that includes 50+ workflow automations across the tool stack (including IT Glue, Autotask, ConnectBooster) and Cooper AI — the third piece of the Kaseya 365 strategy.
• High-Water Mark Pricing Ends: This licensing change will be phased out over 12 to 18 months and eliminates a point of friction with partners.
• Datto Alto 5 Returns: A nod to Datto partners, this move is both symbolic and practical — showing continuity for users within the evolving Kaseya portfolio.
• Infrastructure Investments: Commitments to 99.9% uptime for RMM and BDR services aim to shore up a critical partner concern — reliability at scale.

These announcements underscore Kaseya’s understanding of the need to deliver on tactical initiatives and respond to partner feedback. But product momentum alone won’t resolve the company’s deeper strategic challenges, especially with the CEO role still vacant and questions lingering about long-term leadership, culture, and execution.

Former CEO Fred Voccola dominated Kaseya’s past events as the main speaker in the opening keynote, announcing all the product, acquisition, and strategic news. This year, his name wasn’t even mentioned on the main stage, a notable absence just four months after his departure.

More significantly, the executives who stepped into the spotlight signaled a shift in tone away from aggressive sales and rigid billing toward a more community-focused posture. Notably, while Voccola was absent from the stage this year, he remains involved behind the scenes as board vice chairman and as part of the CEO search committee — a quiet but influential presence in shaping the company’s future leadership.

Execution risks ahead

Challenges remain. Kaseya must integrate its 40-plus products into a cohesive experience while supporting partners who may only use a subset. It must also scale infrastructure to support uptime and reliability goals. Community-building will be difficult among MSPs with fragmented usage patterns and past grievances. The complexity of its portfolio also risks alienating smaller partners who feel overwhelmed or underserved by the broader product strategy.

Additionally, continued friction over licensing terms, support responsiveness, and product interoperability could slow progress if not proactively addressed. Kaseya has an opportunity to lead, but execution, alignment, and communication will determine whether it can.

Outlook

Kaseya has an opportunity to reset its trajectory. With leadership transition underway, momentum in platform bundling, and early steps toward AI integration, the company is positioning itself for the next evolution of managed services. But execution will be critical. The company’s ability to build trust, simplify operations, and lead on AI may ultimately define its success in this next era.