Director of Digital Strategy and Systems

IslandWood • Bainbridge Island, WA

56d • $145,000 - $165,000 • Onsite

About The Position

IslandWood 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 IslandWood’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 IslandWood’s systems connect, evolve, and support the organization’s goals while ensuring sustainability, alignment, and continuous improvement.

Requirements

• Proven experience leading digital transformation, enterprise system integration, and business process optimization with a demonstrated ability to both strategize and implement solutions directly.
• Demonstrated success in managing complex technology ecosystems comprising diverse platforms and cross-functional initiatives.
• Strong project management, communication, and stakeholder engagement skills.
• Strategic thinker who can translate vision into actionable plans and measurable outcomes.
• Demonstrated success in sustained change of leadership and cross-functional collaboration.
• Excellent communication skills with the ability to explain technical concepts to non-technical audiences.
• Experience with Salesforce administration or oversight of similar CRM and related platforms including hands-on configuration, customization, and integration.
• Demonstrated ability to train and empower non-technical staff in the effective use of software, including productivity suites like Microsoft Office.
• A pragmatic, resource-conscious approach to technology, with experience identifying and implementing high-impact solutions within budget constraints.
• Demonstrates sound decision-making under pressure, quickly diagnosing issues and problem-solving in a proactive manner
• Demonstrates excellent judgement and ability to juggle multiple competing priorities
• Must pass child safety screening
• Must be able to comply with and maintain a smoke-free and drug-free work environment

Responsibilities

• Develop and execute a forward-looking digital and technology strategy aligned with IslandWood’s mission and priorities.
• Lead IslandWood’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 IslandWood’s portfolio of business applications, including Salesforce, Marketing Cloud Account Engagement, Active Network, Volunteer Hub, Eventbrite, Sage/Intact FormAssembly, and related integrations leveraging and optimizing our use of MS Office (Teams, SharePoint, Outlook, OneDrive, etc.)
• Ensure applications are aligned, integrated, and optimized to support effective data management and efficient cross and intra-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 with system administrators to ensure high performance, cost effectiveness, and reliability.
• Actively identify and address integration points between diverse platforms (e.g., Salesforce, SAGE, EventPro) to streamline data flow and reduce manual effort.
• Develop and implement a knowledge management strategy that organizes, digitizes, and maintains institutional information in accessible and intuitive ways.
• Define and document standard business processes, ensuring that technology solutions reflect and reinforce these standards.
• Lead user training, adoption, and change management initiatives for both new and existing systems; digital tools and workflows are effectively used, and improvements are sustained.
• Collaborate with cross-functional teams to identify opportunities for automation, streamlined communication, and improved collaboration
• Oversee and coordinate outsourced IT partners responsible for infrastructure, security, and support, ensuring performance aligns with contracts and organizational standards. This role focuses on optimizing software applications and data systems, while infrastructure is managed by external partners.
• Partner with the IT Technician on day-to-day tech and operational needs, ensuring technology supports events, programs, and daily operations.
• Collaborate with Communications and Web teams to maintain the technical performance and integration of IslandWood’s digital platforms.
• Ensure all systems and data are secure, compliant, and aligned with best practices.

Benefits

• 100% IslandWood paid Medical, or a low employee contribution option offered
• 100% IslandWood paid Dental and Vision option
• HSA with IslandWood contribution (based on qualifying medical plan)
• Life/AD&D, Short and Long-term Disability Insurance paid by IslandWood
• 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
• IslandWood 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).

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 51-100 employees