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
• Defines and enforces delivery standards, governance, SOW scoping discipline, and change control; runs a consistent operating cadence (weekly/monthly business reviews, forecast and capacity reviews, risk and escalation forums, and quarterly planning) to drive accountability and operational rigor
• Establishes and owns performance management across delivery and operational efficiency metrics, including utilization and margin, service quality, partner satisfaction, time-to-value, adoption, and retention impact, and provides regular reporting, forecasts, and strategic updates to senior leadership on performance, risks, capacity, partner trends, and improvement initiatives
• Leverages services data and Voice of the Partner insights to identify, prioritize, and lead initiatives that reduce delivery risk, remove friction, and improve implementation quality and scalability • Drives cross-functional interlock with Sales, Product, Partner Success, Support, Enablement, Finance, and Operations to ensure clean handoffs, defined readiness and success criteria, and closed-loop feedback; supports services attach where appropriate; and engages partners and key stakeholders to strengthen executive relationships and promote long-term value realization
• Develops leaders and teams through coaching and talent development while building a culture of accountability, partner obsession, innovation, and continuous improvement
• Represents ConnectWise Consulting in strategic programs and partner/community engagements, including IT Nation, and monitors industry and MSP market trends to continuously improve service delivery and partner outcomes

Working Conditions:

• Remote-US or CAN
• 10-20% Travel may be required