Executive Director

Ryan Mahoney

Ryan Mahoney

Director of Product, FirstWho

“This is the level where charm becomes dangerous. A Strategic Executive Director needs to raise millions while knowing when to walk away from bad money. They need to build partnerships with corporations and governments without becoming their mouthpiece. They need to scale systems while keeping the board from micromanaging operations. The hardest part is finding someone who can do all this with genuine cultural humility, not performative allyship. You want someone who has failed publicly and learned from it, not someone whose resume is a smooth upward line. The $2-15M budget means they have survived the startup chaos but have not yet been cushioned by large infrastructure. They still remember what it feels like to make payroll by Tuesday.”

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Competency Questions

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Governance, Risk & Organizational Excellence

Focuses on scaling organizational infrastructure across multi-site operations, ensuring fiduciary compliance for $2–15M budgets, building senior leadership capacity, and establishing governance systems that support strategic pivots and diversified revenue generation.

Board Governance & Fiduciary Oversight

Manages board recruitment, orientation, and development cycles; implements governance policies, ensures timely regulatory filings, and facilitates committee structures to optimize board performance.

Interview round: Strategic Leadership & Operations

Walk me through a period when you and your board disagreed on a significant strategic direction. How did you navigate that?

Positive indicators

  • Cites specific governance documents or bylaws
  • Acknowledges board's ultimate authority
  • Describes one-on-one cultivation of key members

Negative indicators

  • Blames board for being 'out of touch'
  • Describes going around or circumventing board
  • Suggests board should 'stay out of operations' as sole strategy

Attitude Questions

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Active Listening

The disciplined practice of fully concentrating on, understanding, and retaining what others communicate—verbal and non-verbal—while suspending internal response formulation, judgment, or solution-seeking until comprehension is complete. For Executive Directors, this involves creating conditions where diverse stakeholders feel genuinely heard across power gradients, translating between functional languages, and surfacing latent meaning that shapes effective organizational decision-making.

Interview round: Strategic Leadership & Operations

Describe a time when listening carefully to someone you initially disagreed with changed your understanding of a situation.

Positive indicators

  • Describes specific techniques or mindset for listening
  • Names what they learned that they had not considered
  • Acknowledges difficulty of staying open

Negative indicators

  • Framed other person as finally seeing their point
  • Described listening as tactic to persuade
  • No actual change in position or understanding

Progression Framework

This table shows how competencies evolve across experience levels. Each cell shows competency at that level.

Governance, Risk & Organizational Excellence

5 competencies

CompetencyJuniorMidSeniorPrincipal
Board Governance & Fiduciary Oversight

Supports board operations by preparing meeting materials, managing logistics, and documenting decisions; learns foundational governance protocols, conflict-of-interest policies, and basic nonprofit law compliance.

Manages board recruitment, orientation, and development cycles; implements governance policies, ensures timely regulatory filings, and facilitates committee structures to optimize board performance.

Leads governance transformation initiatives, redesigns board composition for strategic diversity, navigates complex multi-jurisdictional regulatory environments, and manages high-stakes fiduciary crises.

Shapes sector-wide governance standards and best practices; serves as trustee for external institutions and philanthropic entities; influences public policy, regulatory frameworks, and legal structures affecting nonprofit operations.

Financial Stewardship & Sustainability

Assists in budget monitoring, accounts payable processing, and financial report preparation; learns nonprofit accounting standards (FASB), restricted fund management, and basic financial controls.

Develops organizational budgets, manages cash flow forecasting, oversees audit preparation, implements internal financial controls, and manages diversified revenue portfolios including grants and earned income.

Architects complex financial sustainability models, manages reserve strategies and investment portfolios, navigates sophisticated funding mechanisms (program-related investments, social bonds), and leads financial risk management.

Designs sector-level financial innovations and funding collaboratives; leads transformative capital campaigns and endowment strategies; advises on systemic changes to nonprofit funding infrastructure and economic models.

Organizational Capacity & Culture

Supports human resource processes, coordinates training logistics, assists in DEI initiative implementation, and maintains organizational documentation and internal communications.

Leads talent acquisition and development programs, manages performance systems, drives organizational culture change initiatives, and oversees diversity, equity, and inclusion strategy implementation.

Architects organizational design and change management strategies, leads executive team development, institutionalizes equitable practices across all operations, and manages complex union or multi-site workforce structures.

Shapes sector capacity building standards and leadership development models; leads field-wide organizational effectiveness research; advises on mergers, alliances, and network governance structures; influences workforce policy.

Risk Management & Regulatory Compliance

Assists in risk assessment documentation, maintains compliance checklists, and supports data collection for insurance renewals and regulatory audits.

Develops enterprise risk management protocols, manages insurance portfolios, implements internal control systems, and leads compliance reviews across human resources, finance, and program operations.

Architects organization-wide risk frameworks, navigates complex regulatory landscapes (501c3 compliance, lobbying restrictions, international regulations), and leads crisis management and business continuity planning.

Establishes sector risk benchmarks and standards; influences policy to create favorable operating environments; manages multi-entity risk portfolios across federated structures or networks; leads field-wide resilience initiatives.

Sector Infrastructure & Research

Consumes sector research and reports, participates in data collection for field studies, maintains literature databases, and supports internal knowledge management systems.

Collaborates with academic institutions and research intermediaries, contributes organizational data to sector datasets, utilizes research findings for strategic planning, and manages internal evaluation and learning agendas.

Partners with research institutions on major field-building studies, leads organizational knowledge management and learning systems, serves on advisory committees for sector research, and translates research into practice innovations.

Funds and directs large-scale sector research initiatives, shapes nonprofit data infrastructure and open data standards, leads collective impact measurement and knowledge networks, and influences research policy and funding priorities.

Mission Strategy & External Engagement

5 competencies

CompetencyJuniorMidSeniorPrincipal
Community Philanthropy & Participatory Practice

Supports community outreach and engagement logistics, documents community input and feedback, assists in participatory process coordination, and maintains relationships with community liaisons.

Designs participatory grantmaking processes and community advisory structures, manages power-sharing agreements and governance models, facilitates community-led evaluation and strategic planning processes.

Institutionalizes community governance models within organizational structures, leads complex multi-stakeholder coalitions, manages participatory budgeting at scale, and ensures accountability to community stakeholders.

Scales participatory philanthropy and democratic funding models across the sector, influences funder practices toward community control, leads field convenings on power shifting, and advances policy frameworks for community-led development.

Digital Transformation & Data Strategy

Manages digital tools and platforms (CMS, CRM), supports data entry and hygiene, maintains basic cybersecurity protocols, and assists with social media and digital communications.

Leads digital transformation initiatives, optimizes CRM and data systems for fundraising and programs, manages cybersecurity and data privacy compliance, and oversees technology vendor relationships and digital strategy implementation.

Architects enterprise technology strategy and data governance frameworks, leads complex system integrations and migrations, ensures digital equity and accessibility across programs, and manages organizational data infrastructure and analytics.

Shapes sector digital infrastructure standards and data collaboratives, leads multi-organizational technology initiatives, influences tech policy and digital rights frameworks, and advances field-wide cybersecurity and data governance practices.

Impact Measurement & Evaluation

Collects and organizes program data, administers surveys and interviews, assists in database management, and supports basic reporting and data visualization for internal and external stakeholders.

Manages evaluation frameworks and performance measurement systems, leads program learning cycles and improvement processes, designs logic models and theories of change, and balances formative and summative evaluation approaches.

Architects organizational impact strategy and evaluation infrastructure, oversees complex multi-site evaluations, integrates participatory methods with rigorous research standards, and leads organizational learning cultures.

Advances field-wide evaluation standards and methodologies, leads collective impact measurement across sectors, influences funder evaluation practices and reporting standards, and shapes evidence-based policy agendas.

Resource Mobilization & Development

Supports grant writing and proposal development, manages donor databases and stewardship activities, assists with fundraising events, and learns donor relations protocols and ethical fundraising standards.

Leads major donor cultivation and solicitation, manages institutional funder relationships, develops comprehensive fundraising strategies across multiple revenue streams, and supervises development staff and campaigns.

Architects diversified revenue models including social enterprise and innovative financing, leads transformational capital campaigns, manages complex funder consortia, and integrates fundraising with strategic mission advancement.

Transforms sector funding models and philanthropic practices; establishes funding collaboratives and pooled funding instruments; influences donor behavior, public giving policies, and macro-level resource flows to the sector.

Strategic Advocacy & External Relations

Supports advocacy campaigns through research and logistics, tracks legislation and policy developments, manages coalition communication lists, and learns 501c3 lobbying and electioneering rules.

Leads advocacy strategies and campaign management, builds and maintains coalition partnerships, manages government and media relations, and develops strategic communications for policy influence.

Architects multi-year advocacy campaigns and movement building strategies, navigates complex political and regulatory landscapes, leads cross-sector coalitions, and integrates grassroots and grasstops organizing approaches.

Shapes public policy and social movements at systemic levels, leads cross-sector tables and field coalitions, influences electoral and legislative agendas, and advances structural changes to benefit the sector and communities served.