Director of Development

Ryan Mahoney

Why this role is hard · Ryan Mahoney

At this level, fundraisers need to move beyond being individual stars and start building things that stick around after they leave. You want someone who can land a six-figure gift on Tuesday morning, then by Wednesday afternoon walk a junior staffer through handling a donor complaint without jumping in and taking over. The tricky part is finding real evidence they've done both. Most candidates either have great numbers because they rode a well-known organization's coattails, or they've managed people but never actually carried their own portfolio through a rough patch. What you're really hiring for is someone who can sit with discomfort: they don't automatically agree when a donor pushes back, they can tell a board member no when the timing would hurt a community partnership, and they genuinely listen to understand rather than just waiting to talk.

Core Evaluation

Critical questions for this role

The competency and attitude questions below are where the hiring decision is made. They run in the live interview rounds and are calibrated to the level selected above.

20 Competency Questions

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  1. Discipline

    Development Infrastructure and Governance

  2. Job requirement

    Board Governance and Leadership

    Manages board giving campaigns and personal solicitation tracking; orients new board members to fundraising roles; staffs development committee meetings and prepares governance materials.

  3. Expected at Mid

    At this level, board engagement is primarily supportive, with the manager operating under guidance to track giving campaigns, orient new members, and staff development committee meetings. This guided approach ensures baseline board participation and meeting effectiveness without overextending tactical bandwidth away from core revenue and retention goals.

Interview round: Cross-Functional Partnership

Describe how you have prepared or supported board members to participate in fundraising.

Positive indicators

  • Mentions individual coaching or pairing strategies
  • Describes matching requests to specific strengths
  • References board members who grew in comfort over time
  • Acknowledges that not all participation looks the same

Negative indicators

  • Made identical asks of all board members
  • Provided no support or guidance for fundraising activities
  • Ignored board member discomfort or non-participation
  • Focused only on dollars raised not engagement quality

12 Attitude Questions

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Active Listening

The disciplined practice of fully concentrating on, understanding, and accurately interpreting verbal and non-verbal information from others before responding, while simultaneously creating psychological safety that encourages disclosure of tacit knowledge, emotional subtext, and politically sensitive information that shapes strategic decisions.

Interview round: Recruiter Screen

Give an example of translating information between two groups who understood an issue very differently—perhaps donors and program staff, or board and frontline team.

Positive indicators

  • Describes specific language or concepts they bridged
  • Notes misunderstanding they prevented
  • Mentions when they brought parties together directly

Negative indicators

  • Simplified to point of distortion
  • Favored one side's framing
  • Positioned themselves as sole interpreter

Supporting Evaluation

How candidates earn the selection conversation

The goal is to reduce effort for everyone by collecting more useful signal before adding more interviews. Lightweight application prompts and structured screens help the panel focus live time on the candidates most likely to succeed.

Stage 1 · Application

Filter at the door

Runs the moment a candidate hits Submit. Disqualifying answers end the application; everything else is captured for review.

Video-Response Questions

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Application Screen: Video Response

You are presenting a proposed corporate sponsorship to the board, but several trustees insist on accepting funding from a developer with a history of displacing BIPOC tenants in your service area. The revenue is critical for this quarter’s targets. How would you navigate this conversation to uphold your organization’s anti-displacement mission while preserving the relationship and addressing the financial pressure?

Candidate experience

REC
0:42 / 2:00
1Record
2Review
3Submit

Response time

2 min

Format

Recorded video

Stage 2 · Resume Screening

Read the resume against fixed criteria

Reviewers score every application that clears the door against the same criteria. Stronger reviews advance to live interviews; weaker ones are archived without further screening.

Resume Review Criteria

8 criteria
Evidence of tracking qualified prospects through defined cultivation stages, executing disciplined touchpoint sequences, and advancing relationships from identification to solicitation using CRM tools.
Evidence of designing, launching, and optimizing monthly giving programs or stewardship journeys that include automated upgrade paths, retention tracking, and timely impact reporting.
Evidence of managing institutional grant pipelines, coordinating multi-departmental submissions, tracking compliance deadlines, and aligning program outcomes with funder reporting requirements.
Evidence of defining and enforcing CRM data standards, implementing deduplication protocols, and establishing forecasting accuracy benchmarks to maintain audit-ready revenue reporting.

Does the resume show relevant prior work experience?

Does the cover letter or personal statement convey clear relevance and familiarity with the job?

Does the resume indicate required academic credentials, relevant certifications, or necessary training?

Is the resume complete, well-organized, and free from formatting, spelling, and grammar mistakes?

Stage 3 · During Interviews

Where the hire is decided

Interview rounds use the competency and attitude questions outlined above, then add tests, work simulations, and presentations that reveal deeper evidence about how the candidate thinks and works.

Presentation Prompt

Prepare a short deck walking us through a fundraising campaign or major gift stewardship journey you designed or managed. Discuss how you integrated participatory feedback loops, navigated cross-functional constraints, and measured success beyond immediate revenue.

Format

deck-and-walkthrough · 20 min · ~2 hr prep

Audience

Hiring panel (Director of Development, Senior Program Lead, Data/CRM Manager)

What to prepare

  • 3-5 slides outlining the campaign context, your approach to stakeholder alignment, boundary-setting decisions, and outcome metrics.
  • Brief speaker notes to guide your walkthrough.

Deliverables

  • A 3-5 slide deck and a structured verbal walkthrough.

Ground rules

  • Use only work you are permitted to share. If past work is confidential, adapt it to a hypothetical but realistic scenario.
  • Focus on your decision-making, tradeoffs, and communication strategy rather than polished marketing assets.
  • Do not create new strategic plans; reflect on existing or simulated past execution.

Scoring anchors

Exceeds
Transparent about constraints, shows iterative learning from feedback, strong stakeholder alignment, and clear data-to-decision linkage.
Meets
Coherent narrative, addresses core requirements, proposes reasonable boundary-setting, and includes relevant metrics.
Below
Vague on decision rationale, ignores friction or feedback loops, focuses only on top-line revenue, or lacks measurable outcomes.

Response time

20 min

Positive indicators

  • Clearly articulates rationale for pacing, scope boundaries, and cross-functional handoffs.
  • Demonstrates how participatory or donor feedback was operationalized into campaign adjustments.
  • Shows disciplined use of data to inform next steps, donor upgrade pathways, and retention metrics.
  • Acknowledges friction points and explains how they navigated competing stakeholder priorities.

Negative indicators

  • Presents a linear success narrative without acknowledging tradeoffs, friction, or resource constraints.
  • Defers to leadership for all boundary-setting decisions rather than modeling tactical autonomy.
  • Lacks clear linkage between campaign activities and measurable retention or revenue outcomes.
  • Over-relies on top-line metrics while ignoring donor sentiment or community alignment.

Work Simulation Scenario

Scenario. A high-net-worth prospect is ready to commit $500,000 for a community land acquisition project, but they are demanding a rushed, highly visible site visit with current residents next week to finalize the gift. The board chair is pushing you to schedule it immediately to close before the fiscal quarter ends. You know this violates your organization's resident dignity and safety protocols, and it would compromise your established moves management timeline.

Problem to solve. Navigate a conversation with the board chair to protect community boundaries, preserve the donor relationship, and establish a realistic, ethical cultivation timeline without jeopardizing the gift or board support.

Format

stakeholder-roleplay · 35 min · ~2 hr prep

Success criteria

  • Demonstrates active listening to the chair's fiscal urgency and revenue pressure
  • Clearly articulates the ethical and operational risks of a rushed site visit
  • Proposes a concrete alternative that satisfies donor due diligence while honoring resident consent protocols
  • Maintains professional courage by setting firm boundaries without alienating board leadership

What to review beforehand

  • Standard major gift moves management phases (identification, qualification, cultivation, solicitation, stewardship)
  • Our organization's community engagement and resident consent guidelines
  • Basic board-fundraising committee dynamics and fiduciary expectations

Ground rules

  • This is a live 1:1 conversation; treat it as a real-time stakeholder discussion
  • Focus on how you frame tradeoffs, listen, and set boundaries in the moment
  • You are not expected to draft a formal memo or policy document during the session

Roles in scenario

Eleanor Vance, Board Chair and Fundraising Committee Lead (skeptical_stakeholder, played by leadership)

Motivation. Secure the $500k commitment before quarter-end to stabilize cash flow and demonstrate fundraising momentum to the full board

Constraints

  • The donor has a tight travel window and expects immediate access to see impact
  • The board has expressed impatience with 'slow' cultivation processes
  • You must maintain board trust while protecting program staff and residents

Tensions to introduce

  • Question whether resident consent protocols are causing unnecessary delays
  • Emphasize the financial risk of losing the donor if they feel stalled
  • Push for at least a limited, controlled visit if a full one is denied

In-character guidance

  • Maintain a professional, fiscally-driven tone focused on organizational stability
  • Acknowledge ethical concerns but prioritize revenue urgency and board expectations
  • Respond to clear alternatives with pragmatic skepticism before conceding if the logic is sound

Do not

  • Do not solve the boundary-setting problem for the candidate
  • Do not escalate hostility or become personally dismissive of ethical concerns
  • Do not volunteer information about donor preferences unless directly asked
  • Do not coach the candidate on what to say or how to structure the timeline

Scoring anchors

Exceeds
Reframes the rushed visit as a retention risk, surfaces the donor's actual decision drivers through targeted questions, and delivers a phased, consent-aligned alternative that satisfies fiscal urgency while strengthening long-term major gift process integrity.
Meets
Acknowledges board pressure, clearly states the ethical boundary around resident visits, proposes a reasonable compromise timeline, and maintains professional composure throughout the exchange.
Below
Yields to board pressure to schedule the visit, uses dismissive or defensive language, fails to articulate the long-term cultivation impact of compromising consent, or offers no concrete alternative to the rushed timeline.

Response time

35 min

Positive indicators

  • Listens actively to the chair's fiscal concerns before responding, checking for understanding
  • Clearly separates board pressure from donor expectations, articulating specific risks to community trust and long-term retention
  • Proposes a structured alternative (e.g., virtual briefing, staff-led tour, phased consent process) that respects both timelines and dignity
  • Maintains a firm, respectful boundary without apologizing for ethical standards or over-promising

Negative indicators

  • Defers to board pressure and agrees to compromise resident safety protocols
  • Fails to ask clarifying questions about the donor's actual motivations or travel constraints
  • Uses vague or defensive language that escalates tension without offering a viable path forward
  • Frames ethical boundaries as bureaucratic obstacles rather than strategic retention assets

Progression Framework

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

Development Infrastructure and Governance

5 competencies

CompetencyJuniorMidSeniorPrincipal
Board Governance and Leadership

Prepares board meeting materials and minutes for development committee; tracks board giving compliance and assists with board member orientation.

Manages board giving campaigns and personal solicitation tracking; orients new board members to fundraising roles; staffs development committee meetings and prepares governance materials.

Leads board development committee and governance relationships; recruits new board members with giving capacity; manages board fundraising expectations and training.

Shapes board strategy for organizational leadership and fundraising excellence; serves as key advisor to Board Chair; designs governance models that ensure sustainable philanthropic leadership.

Data Analytics and CRM Governance

Enters data with high accuracy and attention to hygiene standards; runs standard reports and assists with list pulls under supervision.

Manages CRM configurations and user permissions; develops custom reports and dashboards; ensures data integrity across integrated systems to support segmentation and forecasting.

Leads data governance strategy and policy development; implements predictive modeling and advanced analytics; manages CRM integrations and data migrations.

Architects organizational data infrastructure; establishes ethical data use policies and privacy frameworks; leverages AI and machine learning for donor insights and predictive fundraising.

Development Operations and Compliance

Processes gifts according to compliance standards and gift acceptance policies; maintains filing systems and assists with audit preparation.

Manages gift processing team and daily operations; ensures audit readiness and regulatory compliance; develops standard operating procedures for revenue handling and restricted gift tracking.

Leads operations strategy including risk management and compliance frameworks; oversees development budget and vendor management; ensures international compliance if applicable.

Architects operational infrastructure for organizational scale; establishes compliance standards across jurisdictions; drives operational excellence through process automation and lean methodologies.

Equity and Community-Centric Practices

Participates in equity training and supports community listening sessions; assists with diverse vendor identification and accessibility compliance in communications.

Implements community-centric fundraising frameworks; ensures diverse representation in marketing materials; manages inclusive donor communications and accessibility standards to meet equity audit milestones.

Leads DEI initiatives within development; redesigns processes to center community voice; coaches team on cultural competency and power dynamics in philanthropy.

Transforms organizational culture toward justice-centered philanthropy; designs systems that redistribute power to communities; leads sector advocacy on ethical fundraising and decolonizing wealth.

Impact Measurement and Evaluation

Collects program data and beneficiary stories for donor reports; assists with basic outcome tracking and data entry in evaluation systems.

Develops impact dashboards and reporting templates for donors; manages reporting schedules and ensures accuracy of outcome data in fundraising materials and grant reports.

Leads impact measurement strategy for the development function; designs theory of change for fundraising communications; manages external evaluation partnerships.

Architects organizational impact framework and learning agenda; influences funder measurement standards and practices; leverages evidence for policy advocacy and revenue diversification.

Revenue Strategy and Multi-Channel Execution

6 competencies

CompetencyJuniorMidSeniorPrincipal
Digital Fundraising and Marketing

Executes scheduled email campaigns, processes digital acknowledgments, and maintains content calendars; assists with social media posting and basic analytics reporting.

Optimizes digital conversion funnels and A/B testing for acquisition campaigns; manages broad-based giving days and peer-to-peer platforms; analyzes channel performance metrics to inform tactical adjustments.

Leads integrated digital strategy across email, web, and social platforms; oversees brand consistency in fundraising communications; manages agency and vendor relationships for digital execution.

Architects digital transformation strategy for the development function; pioneers emerging revenue channels including crypto and NFT philanthropy; establishes industry benchmarks for digital donor engagement.

Donor Retention and Stewardship

Processes gifts with high accuracy, generates acknowledgment letters, and maintains donor records; assists with stewardship event logistics.

Designs and manages donor recognition programs and impact reporting schedules; oversees donor societies and benefits fulfillment; conducts personalized stewardship outreach to improve retention metrics.

Leads donor experience and retention strategy; oversees comprehensive stewardship for principal donors; manages donor advisory boards and recognition councils.

Architects organizational donor centricity philosophy; designs innovative impact demonstration platforms; ensures equity in donor access and recognition across all giving levels.

Institutional and Corporate Funding

Researches foundation and corporate prospects; assists with proposal formatting, boilerplate language maintenance, and deadline tracking.

Manages grant calendar and submission workflows; writes complex narrative proposals and budgets; stewards institutional donor relationships through reporting and compliance management.

Leads corporate partnership and foundation strategy; negotiates multi-year funding agreements; manages funder consortiums and collaborative funding initiatives.

Shapes sector-wide funding collaborations and influences institutional funder priorities; secures transformational restricted and unrestricted funding; designs innovative funding mechanisms such as recoverable grants.

Integrated Communications

Drafts content for newsletters and campaign collateral; assists with cross-channel message scheduling and proofreading.

Manages integrated campaign calendars ensuring message alignment between development and marketing; coordinates cross-functional messaging for appeals and maintains consistent organizational narrative.

Leads integrated campaign strategy and narrative development; oversees brand storytelling for fundraising; manages executive communications and thought leadership content.

Architects organizational narrative strategy; influences sector messaging on key issues; leverages communications for policy advocacy and revenue generation at scale.

Major Gift Cultivation

Conducts donor research and supports stewardship activities; assists with event logistics and prepares briefing materials for senior staff.

Manages a portfolio of mid-level and major donors independently; conducts cultivation meetings, solicitation calls, and recognition activities with moderate supervision while maintaining disciplined moves management.

Directs major gift strategy for principal and leadership donors; manages senior volunteer leadership in peer-to-peer solicitation; closes six and seven-figure commitments.

Serves as primary relationship holder for institutional and principal funders; designs legacy and planned giving strategies; advises executive leadership on donor market positioning.

Strategic Revenue Planning

Assists in data collection for revenue forecasts and maintains planning documentation under direct supervision; supports data entry for pipeline management.

Manages segment-specific revenue targets and tactical planning for annual campaigns; independently analyzes historical trends to project quarterly income and allocate resources across donor segments.

Leads organization-wide revenue strategy development, including multi-year forecasting, scenario planning, and alignment with strategic goals; oversees pipeline health across all channels.

Architects transformational funding models and organizational sustainability strategies; serves as external thought leader on revenue diversification and influences sector-wide funding practices.