Strategic Programs Director

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.

Our company is powered by our connections, our colleagues, and our community. And, we accept all kinds.

Game-changers, innovators, culture-lovers—and humankind.

We invite discovery and debate. We recognize key moments as milestones.

We see you and value you for your unique contributions. Our inclusive, positive culture lays the foundation to ensure every colleague is valued for their perspectives and skills, giving you the choice of how YOU make a difference.

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

General Summary:

The Director of Strategic Programs / Chief of Staff serves as a trusted advisor and strategic partner to senior leadership, driving alignment across key initiatives and ensuring operational excellence. This role is responsible for orchestrating strategic planning, managing cross-functional programs, and enabling executive decision-making through effective governance and communication.

Essential Duties and Responsibilities:

Strategic Alignment & Execution

• Partner with executive leadership to define and communicate strategic priorities, goals, and success metrics.
• Translate high-level strategies into actionable plans and ensure alignment across departments and teams.
• Monitor progress against strategic objectives and provide insights to adjust course as needed.
• Facilitate strategic planning sessions and ensure outcomes are documented and tracked.

Operational Cadence & Governance

• Establish and manage the rhythm of the business, including leadership meetings, quarterly business reviews, and annual planning cycles.
• Develop and maintain governance frameworks to ensure accountability and transparency in decision-making.
• Drive operational efficiency by identifying and resolving bottlenecks in processes and workflows.
• Prepare executive-level reporting and dashboards to support data-driven decisions.

Program Leadership

• Lead cross-functional strategic programs from initiation through execution, ensuring delivery on time and within scope.
• Develop program plans, manage resources, and mitigate risks to ensure successful outcomes.
• Coordinate with internal and external stakeholders to align efforts and resolve issues.
• Continuously improve program management practices and tools to enhance effectiveness.

Executive Partnership & Leadership Enablement

• Act as a thought partner to the executive team, providing strategic counsel and operational support.
• Enable leaders to focus on high-impact priorities by managing communications, follow-ups, and delegated initiatives.
• Support executive visibility and engagement through preparation of presentations, briefings, and stakeholder communications.
• Foster a culture of collaboration, accountability, and continuous improvement across leadership teams.

Knowledge, Skills, and/or Abilities Required:

To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• Ability to manage large projects and processes independently with limited supervision
• Recognized expert in applicable work area
• Ability to situationally adapt and understand new technology/processes as per business needs
• The ideal candidate is a proactive leader with strong business acumen, exceptional organizational skills, and the ability to influence across all levels of the organization.

Educational/Vocational/Previous Experience Recommendations:

• Bachelor’s degree in related field or equivalent business experience
• 8 years of relevant experience

Working Conditions:

• Onsite/Hybrid/Remote depending on location
• 10-20% travel 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.