Sr Director, Professional Services

ConnectWise is an industry and Global leading software company with over 3,000 colleagues in North America, EMEA and APAC. As a community-driven software company dedicated to the success of technology solution providers, our suite helps over 45,000 of our partners manage their businesses better, sell more efficiently, automate service delivery, and remotely control technology so they can consistently deliver amazing customer experiences.

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Curious? Read this opportunity to learn how YOU can make a difference at ConnectWise!

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

ConnectWise is an Equal Opportunity Employer, dedicated to building a diverse and inclusive workforce and providing a workplace free from discrimination and harassment. ConnectWise provides equal employment opportunities to all employees and applicants without regard to race, ethnicity, color, religion, age, sex (including pregnancy), sexual orientation, gender, gender identity or expression, ancestry, national origin, citizenship status, physical or mental disability, genetic information, military/veteran status, marital status, familial or parental status, or any other characteristic or status protected by applicable federal, state and local laws.

The statements above are intended to describe the general nature and level of work being performed by individuals assigned to this job. Other duties may be assigned as needed. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions of the job and/or to receive other benefits and privileges of employment. If you need a reasonable accommodation for any part of the application and hiring process, please contact us at talentacquisition@connectwise.com or 1-800-671-6898.