Director of Digital Strategy and Systems

Position Overview

Island Wood seeks a dynamic, hands‑on Director of Digital Strategy and Systems to lead and execute the organization’s digital transformation and technology vision. This role is ideal for a forward‑thinking, strategic innovator who can also actively implement and optimize solutions. You will ensure that our systems, data, digital processes, and people work seamlessly together—maximizing the value of our existing technology investments, enhancing user experience, improving efficiency, and enabling innovation in service of our mission.

Reporting to the COO, the Director will shape Island Wood’s technology strategy and roadmap, bridging business goals with digital solutions. This includes leading organizational change, modernizing legacy processes, improving knowledge management, ensuring data integrity and integration across platforms, and helping every department leverage technology to advance our mission. The Director will guide how Island Wood’s systems connect, evolve, and support the organization’s goals while ensuring sustainability, alignment, and continuous improvement.

Title:

Director of Digital Strategy and Systems

Reports to:

Chief Operating Officer

Classification:
Full‑time/Exempt

Pay Range: $145,000 to $165,000 Annual

Work Schedule:

Monday-Friday

Work Location:

On-site/Bainbridge Island Campus

• 100% Island Wood paid Medical, or a low employee contribution option offered
• 100% Island Wood paid Dental and Vision option
• HSA with Island Wood contribution (based on qualifying medical plan)
• Life/AD&D, Short and Long‑term Disability Insurance paid by Island Wood
• Voluntary
  
  Employee Benefits:
  
  Life/Hospital/Critical Care Insurance, and Pet Insurance
• Employee Assistance program, Flexible spending accounts and 401k with employer match (after 6 months of employment)
• Variety of Employee Discounts
• Employee Discount for IW Summer Camps

Island Wood offers 3 weeks paid vacation, floating holidays, 10 annual paid holidays and 80 hours of paid annual sick leave (time‑off prorated during first year based on start date).

• Develop and execute a forward‑looking digital and technology strategy aligned with Island Wood’s mission and priorities.
• Lead Island Wood’s digital transformation, identifying opportunities to modernize, automate, and simplify business processes across departments.
• Establish and maintain clear systems of record, ensuring integration, logical data flows, and consistent use of information across platforms.
• Stay ahead of and evaluate emerging technologies and tools, including AI, focusing on practical applications and cost‑effective solutions that can advance mission delivery and improve user and customer experience.
• Partner with leadership to prioritize initiatives, manage the IT budget, and guide investment decisions in technology and systems.
• Serve as the primary advisor to the Leadership Team on technology‑related strategy, innovation, and organizational impact.

• Oversee, continuously improve, and hands‑on configure/manage Island Wood’s portfolio of business applications, including Salesforce, Marketing Cloud Account Engagement, Active Network, Volunteer Hub, Eventbrite, Sage/Intacct, Form Assembly, and related integrations, leveraging and optimizing our use of MS Office (Teams, SharePoint, Outlook, One Drive, etc.).
• Ensure applications are aligned, integrated, and optimized to support effective data management and efficient cross‑departmental workflows.
• Lead system governance and improvement of the organization’s data model, including taxonomy, integrations, and system hierarchy along with consistent protocols for development, change requests, and user access. Ensure proper standards are in place to establish and maintain data integrity.
• Partner with departments to design digital workflows that enhance impact—addressing pain points, replacing manual processes, and reducing duplication.
• Manage relationships with technology vendors, consultants, and partners, along with system administrators, to ensure high performance, cost effectiveness, and reliability.
• Actively identify and…