The Opportunity
Always Dream is seeking a strategic, relationship-driven leader to serve as our next Director of Philanthropy. The Director of Philanthropy is a senior leader reporting to the Executive Director and serving on the Leadership Team. This role is accountable for achieving annual contributed revenue goals aligned with our growth from $3.1M to $4.2M. The Director of Philanthropy leads all fundraising, development operations, and external communications efforts to ensure diversified and growing revenue year over year. Our philanthropy goal makes up about 70-75% of our revenue target; the remainder comes from fee-for-service contributions.
We are seeking a seasoned fundraiser who thrives in relationship-building, event-based fundraising, and major gifts strategy - someone who can think creatively about revenue generation while building the systems and accountability required to sustain growth. This role personally manages a portfolio of major donors (individual, corporate, foundation) and high-capacity prospects, and works closely with the Board of Directors, co-leading the Development Committee with the Executive Director.
What You Will Do
Key Responsibilities
1. Revenue Strategy & Major Gifts Leadership (35%)
- Develop and execute a multi-year fundraising strategy aligned with strategic plan goals, increasing annual revenue targets, and ensuring diversified revenue streams between individual, foundation, corporate, and event fundraising.
- Personally manage and grow a portfolio of approximately 60-90 qualified major donors and high-capacity prospects.
- Lead cultivation, solicitation, and stewardship efforts, including overseeing closing of multi-year and leadership-level gifts.
- Partner with the Executive Director and Founder Kristi Yamaguchi on top-tier donor relationships and solicitations.
- Design and oversee disciplined moves management systems and regular pipeline reviews.
- Identify and implement innovative revenue-generating strategies to diversify funding streams.
- Lead all fundraising events to ensure strong financial performance and meaningful donor engagement.
2. Development Operations & Performance Management (20%)
- Oversee development operations, including Salesforce database integrity, reporting, analytics, gift processing, and acknowledgments.
- Establish clear KPIs and performance metrics for revenue, donor engagement, and team outcomes.
- Collaborate with Finance on forecasting, revenue tracking, and budget alignment.
- Ensure ethical fundraising standards and donor privacy compliance.
- Implement systems that support long-term scalability and sustainability.
3. Team Leadership & Organizational Collaboration (20%)
- Lead, coach, and develop Development & Marketing team of three full-time staff.
- Set clear expectations and hold team members accountable to measurable goals.
- Conduct regular performance reviews and provide ongoing professional development.
- Foster a collaborative, results-driven team culture.
- Serve as a strategic advisor to the Executive Director and contribute to organizational planning as a member of the Leadership Team.
- Collaborate with the Director of Programs to ensure open communication & alignment.
4. Communications & Brand Leadership (15%)
- Lead an integrated marketing and communications strategy that elevates Always Dream’s visibility and leadership in family engagement and early literacy.
- Partner closely with the Communications & Marketing Manager to align storytelling, digital engagement, campaigns, and donor messaging.
- Oversee website, impact reporting, PR strategy, newsletters, and event communications.
- Monitor engagement metrics and refine strategies to strengthen donor acquisition and retention.
5. Board Engagement (10%)
- Co-lead the Board Development Committee and lead its subcommittees including the gala committees
- Equip board members with tools and strategies to support fundraising success.
- Provide regular revenue and pipeline updates to the Board.
- Support board recruitment strategies focused on philanthropic leadership and network expansion
What We’re Looking For
- 5+ years of progressive fundraising experience.
- Proven success securing major gifts and driving revenue growth.
- Strong people manager who builds accountable, high-performing teams.
- Experience working closely with boards and senior leaders.
- Strategic thinker who also enjoys executing.
- Skilled relationship builder comfortable engaging high-level donors.
- Experience with Salesforce or comparable CRM platforms.
- Deep personal integrity and sound judgment.
- Hybrid work environment with expectation to work from Danville office at least twice a month and as needed
- Ability to attend occasional evening and weekend meetings and/or events.
- Ability to travel to Hawaiʻi (no more than 20 days per year; typically 3-4 trips annually)
Benefits
- Medical/Dental/Vision Insurance: These benefits are provided at 100% coverage to full-time employees. If the employee has dependents, their dependents also receive 100% coverage.
- Connectivity Allowance: Full-time employees are eligible for $50 per month allowance for connectivity costs.
- 401K: Always Dream offers an employer sponsored 401K plan which employees are currently eligible for after one month of employment; Always Dream will match up to 3% upon enrollment.
- Vacation: 15 days (120 hours) per fiscal year; can accrue up to 22.5 days (180 hours)
- Sick: 80 hours granted at the beginning of each fiscal year; resets to 80 on July 1 annually
- Holidays & Paid Closure: 10 paid holidays per calendar year, paid summer closure the week of Independence Day, and paid winter closure from Christmas Eve through New Year’s Day
