ConnectWise Appoints New CMO to Lead AI-Driven MSP Platform Positioning

ConnectWise, the Tampa-based software company serving more than 100,000 IT providers worldwide, has appointed Craig Rones as Chief Marketing Officer. Rones, a 20-year veteran of cybersecurity and enterprise technology with past CMO roles at LevelBlue (formerly AT&T Cybersecurity) and Trustwave, will report directly to CEO Manny Rivelo.

His mandate reflects a strategic pivot: translate ConnectWise's expanding AI and automation capabilities into measurable business outcomes for managed service providers (MSPs), particularly around labor efficiency and margin improvement.

The Market Context

The MSP sector is under pressure from three converging forces: accelerating AI adoption, escalating cybersecurity risks, and rising customer expectations. ConnectWise's response is to position its platform — which combines professional services automation, remote monitoring, cybersecurity, and predictive intelligence — as an integrated operating system for MSPs navigating that transition.

The company is leading with what it calls Predictive IT: applied AI intended to help MSPs scale revenue without proportionally scaling headcount.

Key Takeaways

• Marketing is now an AI translation layer: Rones' role is not just brand and demand generation — it's converting complex platform AI features into outcome-based narratives that resonate with MSP owners focused on margins and growth.
• CMO profile is shifting: Rones' background as a CPA in corporate finance and turnaround advisory signals that the role requires connecting AI investment to financial performance, not just technology messaging.
• Platform consolidation is the strategic direction: Historically separate tools for monitoring, security, and service management are converging onto larger platforms, with AI adding another automation layer across all functions.

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