Vice President of Development

Vice President of Development

Full-Time, Exempt, $120,000 – $200,000 Annualized Salary (Bonus Eligible), Hybrid (Up to 4 days a week in person), Full benefits from Day 1

Organization Overview

Breaktime (www.breaktime.org) is a 501(c)(3) non-profit working to break the cycle of young adult homelessness by equipping young adults with the job and financial security they need to establish housing security. Our vision is a world without young adult homelessness. By providing employment, wraparound services, and financial support, Breaktime ensures that every young person has the tools they need to achieve job, financial, and long-term housing security.

Breaktime prides itself on our supportive, flexible, and rewarding work environment. We offer valuable benefits such as unlimited paid time off, Summer Fridays, 401k matching, 100% employer-paid health, dental, and vision insurance, Flexible Savings Accounts, and flexible hybrid work. Breaktime is rapidly expanding as an organization, and we believe there are significant opportunities for advancement.

The Opportunity

Breaktime is seeking a strategic, relationship-driven, and deeply committed Vice President of Development to lead our next chapter of revenue growth and ensure the long-term financial sustainability of our mission.

At its core, this role has three major responsibilities: personally generating significant philanthropic revenue, leading the Development team as a strong, coordinated revenue engine, and serving as an organization-wide leader who supports the CEO, the Board of Directors, and the Executive Leadership Team.

As Breaktime continues to grow, the VP will build scalable revenue streams, develop a robust new-donor pipeline, steward high-priority donor relationships, both new and existing, strengthen institutional and government funding strategies, and help embed a strong culture of development across the organization. We are seeking a high-energy, experienced fundraising leader with a proven track record of securing six- and seven-figure gifts, managing a comprehensive development function, and building the systems, relationships, and team practices needed to raise $10 million or more annually.

What You Will Do

Major Gifts & Revenue Generation, 50%

• Build, manage, and grow your own portfolio of major donors and funding opportunities, leading the full relationship cycle from prospect identification through cultivation, solicitation, and stewardship.
• Proactively identify and cultivate new donor relationships, building a strong major gifts pipeline that expands Breaktime’s philanthropic reach regionally and nationally.
• Partner closely with the CEO on high-priority donor strategy, helping to steward existing CEO-held relationships while thoughtfully growing them over time.
• Serve as Breaktime’s lead major gifts strategist, personally securing six- and seven-figure gifts and helping the organization meet or exceed ambitious annual revenue goals.
• Create and execute a thoughtful donor retention strategy that deepens loyalty, grows multi-year commitments, and strengthens long-term philanthropic partnerships.

Development Team Leadership & Revenue Operations, 30%

• Lead, coach, and support a high-performing Development team, creating a culture of collaboration, accountability, learning, and shared ownership for revenue results.
• Ensure the full Development function operates as a single, coordinated revenue engine spanning major gifts, institutional giving, corporate partnerships, government funding, events, donor communications, and development operations.
• Provide executive oversight for Breaktime’s institutional giving and government grants strategy, ensuring a strong and competitive pipeline of foundation, corporate, and public funding.
• Serve as a strategic advisor on local, state, and federal government funding opportunities, supporting compliance, relationship-building with civic partners, and alignment with Breaktime’s programmatic goals.
• Partner with the Senior Director of Communications to ensure donor-facing messaging, campaigns, annual reports, and public relations efforts are aligned with Breaktime’s brand and fundraising strategy.
• Strengthen development systems, processes, and CRM data practices so that Salesforce is accurate, reliable, and used effectively to track progress, assess performance, and inform revenue strategy.
• Uphold the highest standards of ethical fundraising, transparency, donor confidentiality, and responsible stewardship of contributed revenue.

Executive Leadership & Board Engagement, 20%

• Serve as a key member of the Executive Leadership Team, helping translate organizational strategy into clear priorities, strong execution plans, and sustainable revenue growth.
• Act as a strategic partner to the CEO, providing thought partnership, fundraising strategy, and the tools needed to advance Breaktime’s highest-priority donor and institutional relationships.
• Equip the CEO and Board members with customized briefings, compelling talking points, and tailored engagement strategies that support high-stakes donor conversations.
• Partner with the CEO to engage, activate, and expand the Board of Directors, strengthening their fundraising capacity and helping create accountability around giving goals.
• Collaborate closely with the AVP of Finance and Operations to forecast revenue, manage the development budget responsibly, and support strong financial planning across the organization.

Who You Are

• A Strategic Revenue Leader: You know how to turn ambitious fundraising goals into clear plans, strong relationships, and measurable results. You can see the big picture, but you are also willing to roll up your sleeves and move the work forward.
• A Confident Relationship Builder: You are comfortable leading high-level donor conversations, making meaningful asks, and closing major gifts. You know how to build trust with high net-worth individuals, institutional funders, civic partners, and other key stakeholders.
• A Mission-Driven Storyteller: You can translate Breaktime’s mission into a compelling case for support. You know how to connect donors to the young adults we serve in a way that is honest, respectful, and grounded in impact.
• A Team Builder and Revenue Operator: You know how to lead a development team that works together as one coordinated revenue engine. You bring structure, accountability, coaching, and data-informed decision-making to help the team perform at its best.
• A Government and Institutional Funding Strategist: You understand the complexity of foundation, corporate, and public-sector funding. You know how to support strong proposals, build relationships with civic and institutional partners, and ensure funding opportunities align with organizational priorities.
• A Trusted Executive Partner: You bring sound judgment, strong communication, and a collaborative leadership style. You can support the CEO, Board, and Executive Leadership Team with the strategy, preparation, and follow-through needed to advance Breaktime’s revenue goals.
• An Inclusive Leader: You put diversity, equity, inclusion, and belonging into practice every day. You know how to build a team where people from all backgrounds feel respected, supported, and able to do their best work. Above all, you are deeply committed to supporting the diverse young adults in Breaktime’s programs and making sure their voices are heard.

This Role May Not Be the Right Fit If

This role may not be the right fit if you are looking for a position that is mostly behind the scenes or removed from direct fundraising. The VP of Development will personally build donor relationships, make meaningful asks, and help close significant gifts.

You may also find this role challenging if you prefer strategy without hands-on execution. This leader will need to move comfortably between donor conversations, team leadership, revenue operations, Board engagement, and cross-functional partnership.

This role is best suited for someone who is energized by ambitious revenue goals, hands-on leadership, and the opportunity to help shape Breaktime’s next stage of growth.

Reports to: Chief Executive Officer

Supervisory: Up to 5 direct reports

Qualifications & Experience

• Minimum of 10 years of progressive development and fundraising experience with a focus on major gifts.
• Minimum of 5 years in a senior management role with direct oversight of staff and departmental budgets.
• Demonstrated experience managing a comprehensive development department that raises $10 million or more annually.
• Proven and highly quantifiable track record of personally securing 6 and 7-figure major gifts.
• Proven success designing and closing a multi-million dollar capital campaign, or scaling a fundraising department during a period of rapid organizational growth.
• Strong financial acumen with the ability to partner seamlessly with HR and Finance on budgeting, forecasting, and revenue tracking.
• Familiarity with CRM data architecture, ideally utilizing Salesforce.
• Preferred: Prior experience in human services, workforce development, or youth homelessness.
• Preferred: Certified Fund Raising Executive (CFRE) credential.

Breaktime carefully considers a wide range of compensation factors, including but not limited to prior experience, skills, expertise, location, internal equity, and other considerations permitted by law. The comprehensive remuneration details, inclusive of benefits, will be communicated upon finalization of the employment offer.

We value and welcome equivalent lived and professional experience. Research suggests that qualified women, marginalized identities, Black, Indigenous, and/or Persons of Color (BIPOC), may self-select out of opportunities if they don’t meet 100% of the job requirements. We believe in diversity and inclusivity at Breaktime, and encourage candidates from various backgrounds to apply if they believe they have the necessary skills to thrive in this role.

Breaktime champions radical inclusion. We strive to be an organization where everyone feels welcome, particularly those who are most often excluded and discriminated against. As an Equal Opportunity Employer, Breaktime does not discriminate in its employment decisions on the basis of housing status, race, color, gender, national origin, age, religion, creed, disability, veteran’s status, sexual orientation, gender identity, gender expression, or any other basis that would be in violation of any applicable federal, state, or local law.

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Breaktime prides itself on our supportive, flexible, and rewarding work environment. We offer valuable benefits such as unlimited paid time off, Summer Fridays, 401k matching, 100% employer-paid health, dental, and vision insurance, Flexible Savings Accounts, and flexible hybrid work.