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IslandWood Research Hub

Comprehensive organizational analysis • Updated November 2025

Executive Overview

Organization Snapshot

  • Mission: Experiential environmental education, equity, and climate literacy
  • Founded: 2002 by Debbi and Paul Brainerd
  • Location: 250-acre campus on Bainbridge Island, WA + Seattle-area programs
  • Scale: Serves 30,000 students annually across 50 school districts and 250 schools
  • Status: 501(c)(3) nonprofit | EIN: 31-1654076
  • Key Partnership: Graduate program with University of Washington College of Education

Revenue Model

  • School programs and education services
  • Teacher professional development
  • Donor philanthropy and major gifts
  • Wedding and event venue rentals (starting at $56,000)
  • State grants (recently eliminated - see Strategic Context)

Leadership Analysis

Executive Team

Megan Karch - Chief Executive Officer

Tenure: Since 2018 (7 years)

  • Previous Role: CEO of FareStart (18-year tenure)
  • Key Achievement: Led FareStart's significant expansion addressing homelessness in Greater Seattle
  • Current Focus: Scaling impact, community partnerships, sustainable nonprofit models
  • Advocacy: Co-Legislative Chair of Washington Outdoor School Coalition (WOSC)
  • Board Service: PCC Community Markets Board member

Kathy Kalstrup - Chief Operating Officer

Tenure: Joined 2024 (New hire - prospective manager)

  • Background: Executive roles in tech and professional services
  • Previous Companies: Aon, Hewitt Associates, Milliman, Fresh Consulting
  • Education: BS in Actuarial Science, University of Illinois
  • Relocated: Moved to Bainbridge Island in 2020
  • Community Engagement: Board member of Housing Resources Bainbridge; Vice President, Bainbridge Island Rowing
  • Focus: Organization-wide operations, systems, and process improvement

Jennifer Kim - Vice President of Philanthropy

Tenure: Joined 2019 (6 years)

  • Experience: 25+ years of fundraising leadership
  • Previous Roles: Director of Major and Planned Gifts at Virginia Mason; Development Officer at Mayo Clinic; Development Director at Eagle Bluff Environmental Learning Center; Director of Individual Giving at Seattle Children's Home
  • Credentials: BA from Willamette University; Certificate in Fundraising Management (UW); Certified Fundraising Executive (CFRE)
  • Enterprise: Founder and Director of Operations, Philanthropy Works (fundraiser training)
  • Focus: Donor strategy, major gifts, philanthropic operations
  • Residency: Lives on Bainbridge Island

Additional Leadership

  • Brenda Hamilton - Director of Finance
  • Tori di Lillo - Event Sales and Planning Manager
  • Director of People & Culture - HR, culture, training, organizational development
  • Director of Urban School Programs - Seattle-area educational initiatives
  • Director of Youth & Family Programs - School programs, camps, community learning
  • Major Gifts Director - Donor relations and CRM/integrations

Board of Directors

Size: 20-member Board (2024/25)

Current Focus: Engaged in strategic planning process to:

  • Clarify the change IslandWood wants to be in the world
  • Further measure organizational impact
  • Structure a sustainable financial future for the next 20 years

Current Board Leadership

Ellie Fields
Board Chair

CEO & Co-founder, Ridge AI

  • • Formerly Chief Product & Engineering Officer at Salesloft (sales workflow platform with AI)
  • • Previous experience at Tableau and Microsoft
  • • Board Chair focused on connecting people to nature and environmental stewardship
Camille Gibson
Board Secretary

CEO, The Real Coconut Products Co.

  • • 32 years at General Mills, VP of Marketing for Cheerios, Wheaties, Nature Valley, Cascadian Farms
  • • Retired from General Mills in 2015 after distinguished career
  • • Named Adweek "Brand Genius" and Fast Company's "100 Most Creative People in Business"
  • • Known for groundbreaking diverse family marketing campaigns
Marguerite Kondracke
VP at Large

Social Entrepreneur & Retired CEO, America's Promise

  • • 40-year career in public, private, and nonprofit sectors focused on education and families
  • • Former CEO of America's Promise (founded by Colin Powell)
  • • Co-founded Bright Horizons, largest provider of workplace child care
  • • Duke University graduate, serves on Duke Board of Trustees
  • • UW Foundation Board & UW Global Health Leadership Council member

Current Board Members

Laura Clise

Founder & CEO, Intentionalist | Senior Advisor, Impact Finance Center

Platform supporting diverse local businesses. Previously led sustainability at Weyerhaeuser. Also serves on Athlete Ally board.

Audrey Haberman

CEO, Sheri and Les Biller Family Foundation

Joined foundation 2021 from The Giving Practice (11 years). Focus on supportive care, workforce development, social impact theatre, public education.

Sara Moorehead

Retired SVP Cooperative Affairs, BECU | Community Volunteer

Retired from BECU 2019 after 6 years leading community engagement. Currently End-of-Life Doula. Lives on Bainbridge Island.

Sara Otepka

Board Member

Experience with Restore Hyper Wellness, Big Blue Swim School, Level 5 Capital Partners, CorePower Yoga.

Ed Thomas

Managing Partner, Deloitte Seattle Office (former)

Leads Strategic Client Program. Board/advisor roles: Social Venture Partners, Seattle Foundation, Equal Opportunity Schools, Powerful Schools, Business Partnership for Early Learning.

Dr. Dan Meyer

Retired Dentist, Scientist & Educator

International advisory experience: WHO, FDI World Dental Federation, ISO, UN Environment Programme, EPA, CDC, NIH, FDA. Lives on Bainbridge Island.

Ben Nimmergut

VP Engineering Functions, Washington State Design Centers

Engineering leadership focused on design center operations.

Chasity Malatesta

Educator, Facilitator & Equity Advocate

Multinarratives LLC. Education consultant, community connector, speaker on equity and inclusion.

Ty Cramer

Community Volunteer | Board Chair, Lakeside School

Mother of six. Former Childbirth Educator and doula. UW Foundation Board (Undergraduate Academic Affairs). UW Global Health Leadership Council.

Howard Wollner

Chairman, NPR Foundation | Board Member, NPR Inc.

Board member Contemporary Jewish Museum (San Francisco). BA History (Georgetown), MBA (Seattle University).

Beth

Strategic Planning & Non-Profit Leadership

20+ years experience. MBA Marketing (UCLA), BS Finance/Accounting (UC Berkeley). Expertise: investment real estate, consumer products (Nestle USA, Clorox), education, arts. Bainbridge Art Museum board.

Katherine Schuitemaker

15-Year Board Member | Former Board Chair

Former Board Chair of Washington Technology Industry Association (14 years member, 2 years chair). Passionate about ensuring world-changing ideas achieve sustained success.

Fraser Black

Managing Partner, Pioneer Square Investments

25+ years angel investor/advisor to early-stage businesses and nonprofits. 35+ years financial/general management: ONYX Software, Ashton-Tate, Salomon Brothers.

Martha Kongsgaard

Lawyer | Philanthropist | Environmental Advocate

Board and executive committee member. Chaired major IslandWood capital campaigns including expansion. Co-founded Kongsgaard-Goldman Foundation (environmental/social justice/arts in PNW).

Dave Goldberg

President, Mithun | AIA Fellow

Lead designer of IslandWood's 250-acre campus (LEED Gold). Board member since 2011. Mithun won 2023 AIA Architecture Firm Award (highest AIA honor).

Yoko Okano

Founding Partner, First Row Partners

Venture capital firm. Stanford University. Board member Sustain Music (using music to connect genres, people, spaces). Based in Seattle.

Board Emeritus Members

Debbi Brainerd
Co-Founder

Co-founded IslandWood with husband Paul in 1999. Former Board Chair. Also former Board Chair of Bloedel Reserve. Remains actively involved.

Dwight Sutton
Emeritus

Retired Mayor of Bainbridge Island. Retired professor, UW School of Medicine (Otolaryngology, Head and Neck Surgery). Former director/senior scientist, Virginia Mason Research Center. Bainbridge Open Space Commission.

Kim Ackerley
Emeritus

Partner and Co-Founder of Ackerley Partners, LLC. President and Executive Director of The Ginger and Barry Ackerley Foundation.

Dr. Pat Wasley
Emeritus

Former Dean, UW College of Education (2000-2012).

Research Note: Board information compiled from publicly available sources including IslandWood website, LinkedIn profiles, news articles, and nonprofit databases. Complete financial/compensation data available in Form 990 filings (Section VII).

⚠️ Organizational Health Signals

Employee Review Findings (2023-2024):

  • "Turnover seems high. Expect a new CEO periodically."
  • Multiple reviews reference upper management concerns
  • Recent COO hire (2024) may signal operational restructuring

This indicates potential organizational transition or culture challenges worth exploring in interview process.

Financial Health

Financial Overview

EIN: 31-1654076

Classification: Classified as a school by IRS (June 2023 filing)

Form 990 Availability

Public financial documents available through:

  • ProPublica Nonprofit Explorer: projects.propublica.org/nonprofits/organizations/311654076
  • Charity Navigator: charitynavigator.org/ein/311654076
  • GuideStar: Forms 990 for 2022, 2023, 2024 available (requires free account)
  • IslandWood Website: islandwood.org (posted their 2020 Form 990 directly)

Note: Detailed financial data (revenue, expenses, assets) for 2022-2024 requires accessing the PDF Form 990 documents through the sources above. Extracted summary data not publicly displayed in nonprofit databases at time of research.

Revenue Streams

1. Educational Programs

School overnight programs, day programs, teacher professional development serving 30,000 students annually across 50 school districts

2. Philanthropic Support

Major gifts, donor campaigns, and philanthropic operations led by VP of Philanthropy Jennifer Kim

3. Event Venue Rentals

Wedding pricing starts at $56,000 for multi-day celebrations on 250-acre property. Described as earned revenue supporting mission.

4. State Grants (ELIMINATED - See Strategic Context)

Previously received Outdoor Learning Grants from WA State - now zeroed out in latest budget

5. Graduate Program Partnership

Partnership with University of Washington College of Education. IslandWood provides $500/month stipend to graduate students ($5,000 per calendar year per student)

Financial Documents

Annual Reports

IslandWood's annual reports provide comprehensive overviews of programs, impact, and financial health.

IRS Form 990 Tax Filings

Form 990 documents provide detailed financial information including revenue, expenses, assets, executive compensation, and program activities.

Form 990 Schedules (Detailed Breakdowns)

Individual schedules provide detailed information on specific aspects of the organization's finances and operations.

Note: All financial documents are publicly available records. Annual reports provide narrative context and program highlights, while Form 990 documents contain detailed financial data required by the IRS for tax-exempt organizations.

Financial Analysis: A Three-Year Trajectory

Based on analysis of FY22, FY23, and FY24 financial documents, IslandWood presents a complex financial picture: strong underlying assets supporting an educational mission, offset by persistent operational deficits that require strategic attention.

📈 Revenue Growth: Steady Upward Trajectory

IslandWood has demonstrated consistent revenue growth over the three-year period:

FY22
$3.43M
FY23
~$3.5M
+2% growth
FY24
~$3.8M
+8.6% growth

Three-year growth: $370,000 increase (10.8% cumulative) demonstrates organizational resilience and growing community support despite external challenges including pandemic recovery and state funding uncertainty.

💰 Revenue Composition: Diversified Income Model

FY22 data reveals a balanced revenue portfolio reducing dependency on any single source:

Program Services Revenue53%
$1,815,937

School programs, education services, teacher professional development, and event venue rentals

Contributions & Grants44%
$1,500,765

Philanthropic support, major gifts, foundation grants, and individual donations

Investment Income2%
$84,763
Other Revenue1%
$28,360

Strategic Strength: The near-equal split between earned revenue (53%) and philanthropic support (44%) demonstrates both mission sustainability through direct services and strong community confidence in the organization's value.

⚠️ Operating Results: Persistent Deficits with Improving Trend

Despite revenue growth, IslandWood has operated at a deficit for three consecutive years, though the situation shows improvement:

FY22
-$185,733
Revenue: $3.43M | Expenses: $3.62M
FY23
Small deficit
Revenue: ~$3.5M | Expenses: ~$3.6M
FY24
-$100,000
Revenue: ~$3.8M | Expenses: ~$3.9M

Positive Signal: Deficit Reduction

The deficit has decreased by approximately 46% from FY22 to FY24 (from -$186K to -$100K), indicating management's focused attention on financial sustainability. However, expenses continue to track closely with revenue growth, suggesting structural cost challenges that require ongoing strategic attention.

💪 Balance Sheet: Exceptional Financial Foundation

Despite operating deficits, IslandWood maintains a remarkably strong financial position (FY22 data):

Total Assets
$11.57M
Total Liabilities
$578K
5% of assets
Net Assets
$10.99M
95% equity ratio

Financial Cushion: With nearly $11 million in net assets, IslandWood has substantial reserves to weather financial challenges. This strong balance sheet provides:

  • Multi-year runway to address operating deficits
  • Capacity to invest in strategic initiatives and infrastructure improvements
  • Financial credibility with donors, grantmakers, and lending institutions
  • Flexibility to navigate economic downturns and funding disruptions

🎯 Strategic Implications

The Sustainability Challenge

While the strong asset base provides breathing room, persistent deficit spending is unsustainable over the long term. At the current FY24 deficit rate of $100,000/year, net assets would erode by $1 million over a decade—manageable given the $11M base, but concerning if deficits don't continue to improve or worsen due to state funding elimination.

Board's 20-Year Planning Imperative

The board's current focus on "structuring a sustainable financial future for the next 20 years" is directly addressing this challenge. With state Outdoor Learning Grants eliminated, the organization must either:

  • Increase revenue through expanded philanthropy, higher program fees, or new earned income streams
  • Reduce expenses through operational efficiencies and process optimization
  • Both - the most likely path forward
Digital Strategy as Financial Lever

The Director of Digital Strategy & Systems role becomes mission-critical in this context:

  • Revenue enablement: Optimized CRM and donor management systems to increase philanthropic efficiency and major gift pipeline development
  • Cost reduction: Process automation and system integration to reduce administrative overhead
  • Data-driven decisions: Integrated financial and operational data enabling board and leadership to make informed strategic choices
  • Scale without proportional costs: Technology enabling IslandWood to serve more students while controlling expense growth

Bottom Line: IslandWood is financially strong but operationally strained. The organization has the assets and community support to succeed long-term, but requires strategic transformation to align expenses with sustainable revenue—making this an opportune moment for impactful digital systems work.

Strategic Context & Current Challenges

🚨 CRITICAL: Washington State Funding Elimination (2025)

The Washington State Legislature zeroed out the Outdoor Learning Grants program in the latest budget.

Impact by the Numbers:

  • Previous Funding: $20 million in last two-year budget (doubled from prior cycle)
  • New Allocation: $0 for new grants
  • Remaining Funds: Only ~$1.4 million leftover to support 50-60 highest-need schools in 2025-26
  • Schools Affected: Approximately 730 schools signed up for 2024-25; ~790 expected to apply for 2025-26
  • Example Impact: Bellingham School District lost $190,125 in subsidies (out of $200,000 total cost for all 5th graders)
  • Casualties: Vancouver Public Schools anticipates eliminating outdoor school entirely due to funding cuts

Strategic Implications for IslandWood:

  • Significant revenue loss from school program subsidies
  • Need to pivot to alternative funding models
  • Increased pressure on philanthropy and major gifts operations
  • Potential reduction in student reach and equity mission
  • Board's 20-year sustainability planning becomes even more critical

Advocacy & Public Stance

Washington Outdoor School Coalition (WOSC)

  • CEO Megan Karch serves as Co-Legislative Chair of WOSC
  • Focused on advocating for fully funded outdoor school experiences for every Washington student
  • Public stance on state funding cuts demonstrates organizational commitment to advocacy
  • Strong brand visibility in Seattle environmental education space
  • Emphasis on equity, access, and climate literacy in public messaging

2024/25 Strategic Priorities

Board and leadership currently engaged in strategic planning to:

  • Clarify Impact: Define the change IslandWood wants to be in the world
  • Measure Success: Develop stronger impact measurement frameworks
  • Financial Sustainability: Structure sustainable financial model for next 20 years
  • Donor Diversification: Reduce dependency on state funding
  • Program Impact: Maintain student reach despite budget constraints

Programs & Impact

Core Educational Programs

School Overnight Program

  • Audience: 4th-6th grade students and teachers
  • Format: Multi-day immersive experiences on 250-acre Bainbridge Island campus
  • Focus: Hands-on learning in nature, science enthusiasm, team leadership, environmental stewardship
  • Reach: Primary program serving majority of 30,000 annual students
  • Reopening: Resumed after pandemic with strong advocacy for universal access

Urban Programs

  • Locations: Brightwater Center (Woodinville), South Plant (Renton), Duwamish River, Seattle parks
  • Focus: Broadening "environment" to include urban systems and human impacts on ecosystems
  • Goal: Expanding access to nature-based learning beyond island campus
  • Reach: Serves Seattle-area schools and communities

Teacher Professional Development

  • Focus: Climate literacy and community-based teaching
  • Goal: Multiplying impact by training educators to integrate environmental education
  • Format: Workshops, training programs, ongoing support

Youth & Family Programs

  • Offerings: Nature programming, camps, community learning opportunities
  • Audience: Families and youth outside of formal school partnerships
  • Goal: Expanding environmental education access to broader community

Graduate Program Partnership

University of Washington Partnership

Official Name: IslandWood Graduate Program in Education for Environment and Community

Program Structure:
  • Duration: 10-month graduate residency (late August - mid June)
  • Credential: Completes first year of UW Master's in Education; fulfills prerequisites for Master's in Teaching in Elementary Education
  • Partnership: UW College of Education (top-ranked program)
  • Location: Based on 250-acre Bainbridge Island campus (35-minute ferry from Seattle)
Curriculum:
  • Graduate-level coursework in environmental education through justice-oriented lens
  • Biweekly outdoor teaching experiences
  • 1:1 mentoring for graduate students
Financial Support:
  • Stipend: $500/month during 10-month program ($5,000 per calendar year per student)
  • Application: Dual application to both IslandWood and UW M.Ed. program required

Strategic Value: This partnership positions IslandWood as a nationally recognized leader in environmental education with academic credibility and pipeline for high-quality educators.

Impact Metrics

30,000
Students Served Annually
250
Schools Participating
50
School Districts
2,000,000+
Hours of Nature-Based Learning Since Founding

Campus & Facilities

  • Primary Campus: 250-acre learning center on Bainbridge Island
  • Features: Living classroom with diverse ecosystems, overnight facilities, event spaces
  • Sustainability: Living Machine water treatment system demonstrating environmental stewardship
  • Multi-Use: Educational programs + wedding/event venue generating earned revenue
  • Access: 35-minute ferry ride from downtown Seattle

Competitive Landscape

IslandWood operates within a competitive but collaborative ecosystem of Pacific Northwest environmental education nonprofits. Key organizations in the space:

NatureBridge

DIRECT COMPETITORPARTNER ORGANIZATION
  • Programs: Overnight environmental science programs in Olympic National Park (similar model to IslandWood)
  • Geographic Scope: National presence with programs in multiple national parks
  • Focus: Students spend multiple days immersed in nature within national parks
  • Family Programs: Connects families with Olympic National Park
  • Partnership: Listed as IslandWood partner organization
  • Differentiation: Focused on national park settings vs. IslandWood's dedicated campus

North Cascades Institute

DIRECT COMPETITOR
  • Founded: 1986 (16 years before IslandWood)
  • Recognition: Nationally recognized environmental education nonprofit
  • Focus: Empowering people to explore mountains, rivers, forests, and wildlife of Pacific Northwest
  • Facility: North Cascades Environmental Learning Center on Diablo Lake in North Cascades National Park
  • Partnership: Operates in partnership with National Park Service and City of Seattle
  • Key Program: Mountain School - nationally recognized program for 5th graders in North Cascades National Park
  • Adult Programs: Popular outdoor getaways whose fees help finance youth education programs (similar revenue model to IslandWood)
  • Specialty Programs: Teenage girls glacier study on Mount Baker; all-expense wilderness trips for low-income teens
  • Differentiation: Mountain/alpine focus vs. IslandWood's forest/island ecology

Wilderness Awareness School

RELATED COMPETITOR
  • Programs: Summer camps and youth nature programs in Pacific Northwest
  • Focus: Wilderness skills and nature connection
  • Differentiation: Skills-based outdoor education vs. IslandWood's science/climate literacy focus

Audubon Programs (Bird Alliance of Oregon, National Audubon Society)

RELATED COMPETITOR
  • Programs: SWIFTS Nature Summer Camp, Outdoor Naturalists (grades 6-8)
  • Focus: Bird conservation, Pacific Northwest ecosystems, wilderness skills
  • Format: Art, science experiments, games combined with regional explorations
  • Mission: Protecting birds and critical habitats using science, advocacy, education
  • Differentiation: Wildlife/bird conservation focus vs. IslandWood's broader environmental education

Competitive Positioning Analysis

IslandWood's Unique Advantages:

  • Dedicated 250-acre campus (vs. programs operating within national parks)
  • UW partnership providing graduate education pipeline and academic credibility
  • Proximity to Seattle (35-minute ferry) for easy school access
  • Multi-day overnight programs creating immersive experiences
  • Urban program expansion reaching students beyond island campus
  • Earned revenue diversification through high-end wedding/event venue
  • Climate literacy and equity focus aligned with contemporary educational priorities
  • Strong advocacy presence through Washington Outdoor School Coalition

Collaborative Ecosystem:

IslandWood partners with several "competitors" including NatureBridge, Pacific Education Institute, The Nature Conservancy, and Washington's National Park Fund. This indicates a collaborative rather than zero-sum market where organizations work together to expand outdoor education access statewide.

Strategic implication: Director of Digital Strategy & Systems role will likely involve cross-organizational collaboration and knowledge sharing within environmental education sector.

Key Strategic Insights

1. Digital Strategy & Systems Critical to Financial Sustainability

With state funding eliminated, IslandWood must maximize efficiency and diversify revenue. The Director of Digital Strategy & Systems role becomes mission-critical to:

  • Optimize donor management and philanthropic operations (CRM integration)
  • Streamline school registration and program management systems
  • Improve data integration to reduce operational costs
  • Enable data-driven decision making for the board's 20-year sustainability planning
  • Support Major Gifts Director with technology for donor relations

2. New COO = Operational Transformation Opportunity

Kathy Kalstrup joined as COO in 2024 with mandate for "organization-wide operations, systems, and process improvement." As prospective manager:

  • Likely open to digital transformation and modernization
  • Background in tech/consulting (Milliman, Fresh Consulting) suggests systems thinking
  • Fresh perspective on legacy processes creates change opportunity
  • Director of Digital Strategy & Systems will be key partner in operational transformation

3. Organizational Culture: Proceed with Awareness

Employee reviews mentioning turnover and management concerns warrant careful evaluation:

  • New COO hire may indicate response to operational/cultural challenges
  • Change management skills will be essential
  • Building trust and staff buy-in critical for digital adoption
  • Interview process: Explore org culture, staff engagement, change readiness

4. Mission Alignment Opportunity

IslandWood's focus on equity, climate literacy, and access to nature-based learning for under-resourced students provides strong mission alignment for values-driven candidates:

  • Technology as enabler of equity and access
  • Systems work directly supports reaching 30,000 students annually
  • Digital strategy can amplify advocacy and public education efforts
  • Climate-focused mission aligns with contemporary values

5. Urgency Factor: Financial Crisis Creates Implementation Imperative

State funding elimination creates urgency for digital transformation:

  • Board engaged in sustainability planning NOW
  • 730 schools losing subsidies = massive operational impact
  • Organization needs quick wins and demonstrable ROI from systems improvements
  • Candidate should be prepared to hit ground running with immediate impact
  • 90-day plan essential for establishing credibility and momentum

6. Data Integration as Organizational Backbone

Multiple systems across donor relations (CRM), school registration, operations, and program delivery create integration opportunity:

  • Major Gifts Director needs CRM/integration support
  • VP of Philanthropy overseeing donor strategy requires unified data view
  • School program directors need streamlined registration and tracking
  • Finance director needs integrated financial and operational data
  • Cross-departmental alignment through shared systems = candidate mandate

Recommended Interview Questions

Financial Sustainability & Strategy

  • How is the organization responding to the elimination of Washington State Outdoor Learning Grants? What's the financial impact, and what's the recovery plan?
  • What does the board's 20-year sustainability planning process look like, and how does digital strategy fit into that vision?
  • What are the current revenue targets for philanthropy, earned income (weddings/events), and program fees?
  • How is the organization thinking about donor diversification and major gifts pipeline development?

Systems & Technology Current State

  • What systems are currently in place for CRM, donor management, school registration, and operations?
  • What are the biggest pain points with current technology and processes?
  • What integrations exist today, and what are the gaps?
  • What's the technology budget, and how are tech investments currently prioritized?
  • What does the IT/tech team structure look like? Who would I be working with?

Organizational Culture & Change Readiness

  • What's the organizational appetite for change and digital transformation?
  • How would you describe staff comfort level with technology and new systems?
  • What change management approaches have worked well (or not worked) in the past?
  • I noticed the COO role is new (2024) - how is the operational transformation going so far?
  • Can you describe the organization's approach to cross-departmental collaboration?

Role Expectations & Success Metrics

  • What would success in this role look like in the first 90 days? First year?
  • What are the highest priority systems or processes that need attention immediately?
  • How do you envision this role evolving as digital infrastructure matures?
  • What's the relationship between this role and the Major Gifts Director regarding CRM/integration work?
  • What decision-making authority would I have for technology choices and vendor selection?

Leadership & Team Dynamics

  • Kathy, what brought you to IslandWood as COO, and what are your top operational priorities?
  • How does the executive team work together, and what's the communication cadence?
  • What's your management style, and what do you value most in direct reports?
  • How does this role interact with program directors, finance, and philanthropy teams?

Research Methodology & Sources

Research Approach

This analysis compiled publicly available information from multiple sources including:

  • IslandWood official website and leadership bios
  • News articles and press releases (2024-2025)
  • Washington state legislative and budget documents
  • Nonprofit financial databases (ProPublica, Charity Navigator, GuideStar)
  • University of Washington College of Education partnership information
  • Employee reviews and organizational reputation sources
  • Competitive organization websites and programs
  • Social media and professional networking profiles

⚠️ Research Limitations

  • Detailed financial data (revenue, expenses, assets) for 2022-2024 requires accessing PDF Form 990s through nonprofit databases
  • Complete board member roster not publicly available in web research (available in Form 990 filings)
  • Internal organizational culture assessment based on limited employee review data
  • Specific technology stack and systems architecture not publicly documented
  • Historical turnover data and specific leadership transitions not fully available

Recommended Next Steps

1. Access Form 990 Financial Documents

Obtain detailed financial data for 2022-2024 from:

  • ProPublica Nonprofit Explorer: View IslandWood 990s
  • GuideStar: Create free account to access recent filings
  • Review: Total revenue, expenses, assets, liabilities, key personnel compensation, program vs. admin costs

2. Network with IslandWood Connections

  • Reach out to UW College of Education contacts who work with the graduate program
  • Connect with environmental education professionals in Seattle area
  • Explore LinkedIn connections to current or former IslandWood staff
  • Attend Washington Outdoor School Coalition events if possible

3. Develop Role-Specific Positioning

Based on this research, position yourself as:

  • "Digital Backbone for Mission" architect who connects technology to educational impact
  • Change agent who can navigate organizational transition with COO partnership
  • Pragmatic implementer who delivers quick wins while building sustainable infrastructure
  • Mission-driven technologist passionate about equity, access, and environmental education

4. Prepare 90-Day Plan Framework

Given financial urgency, develop preliminary 90-day plan to demonstrate readiness:

  • Days 1-30: Discovery (systems audit, stakeholder interviews, quick wins identification)
  • Days 31-60: Strategy (integration roadmap, priority ranking, resource planning)
  • Days 61-90: Implementation kickoff (first integration, staff training, success metrics)

5. Visit Campus (If Possible)

If opportunity arises before final interviews, visit the Bainbridge Island campus to:

  • Experience the mission firsthand
  • Understand operational context and physical infrastructure
  • Meet staff informally and gauge culture
  • Demonstrate genuine interest and commitment

Research completed: November 2025
For: Director of Digital Strategy & Systems role exploration
Status: Autonomous research compilation - comprehensive organizational analysis