About Always Dream

At Kristi Yamaguchi’s Always Dream, we ensure children have access to high-quality books in the home and meaningful family engagement support. Through our Always Reading™ program, we partner with Title I schools in Northern California and Hawaiʻi to serve Pre-K, TK, and Kindergarten students and their families—building joyful reading routines that lay the foundation for lifelong literacy. With a current budget of $3.1M and projected growth to $4.2M, we are entering an exciting phase of expansion and long-term sustainability.

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

• 8–10+ 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