Sr Director, Professional Services

General Summary

The Sr. Director of Professional Services leads the ConnectWise Consulting organization and is accountable for predictable, high-quality execution of non-scale (high-touch, complex) consulting engagements, partner outcomes, and operational rigor across Consultants, Project Managers, and Technical Services. The role owns short- to midterm strategy execution and operating direction for the organization, including performance management across delivery quality, partner satisfaction, time-to-value, adoption, retention impact, and operational efficiency (utilization and margin). A core focus is Consulting360, the flagship service offering—owning execution excellence and ongoing evolution of the delivery model, assets, and enablement to expand ConnectWise Consulting into a business consulting function with measurable partner impact. The Sr. Director defines and enforces delivery standards and governance, including SOW scoping discipline and change control, and runs a consistent operating cadence to drive accountability and operational rigor. The role drives cross-functional interlock with Sales, Product, Partner Success, Support, Enablement, Finance, and Operations, including alignment that supports services attach where appropriate, and closed-loop feedback that removes friction and improves partner outcomes. The Sr. Director drives an AI & Automation-first strategy and execution by adopting tools and workflows that improve efficiency, quality, scalability, and insights. The role provides regular reporting and forecasts to senior leadership and monitors industry and MSP market trends to continuously improve delivery.

Essential Duties & Responsibilities

• Leads Consultants, Project Managers, and Technical Services to deliver non-scale consulting engagements across the ConnectWise portfolio, improving partner time-to-value, adoption, satisfaction, and retention
• Drives an AI & Automation-first strategy and execution by adopting and building tools and workflows that improve efficiency, quality, scalability, insights, and partner outcomes
• Owns short- to mid-term strategy execution and operating direction for the ConnectWise Consulting organization, including organizational planning, talent strategy, capacity modeling, and integration of acquired teams, workflows, offerings, and partner experience standards
• Partners with executive leadership on matters of significance to ConnectWise and serves as an executive escalation point for high-impact partner issues and complex delivery challenges
• Owns the Consulting360 service execution and continuous refinement, including delivery governance, methodology evolution, playbooks, enablement, and measurement to elevate ConnectWise Consulting into a business consulting function with measurable partner impact