Senior Director, Development

About Career Pathways Initiative

Career Pathways Initiative (CPI) is a fast-growing nonprofit that helps first-generation, low-income (FGLI) college students build the skills, networks, and confidence to launch successful careers.

Through partnerships with leading universities and employers, CPI provides career coaching, professional development, networking opportunities, and access to internships and full-time employment. Our students are exceptionally talented. They simply have not had the same access to career networks and opportunities as many of their peers. CPI exists to change that.

The Opportunity

CPI is seeking an entrepreneurial and experienced Senior Director of Development to lead and grow our fundraising efforts during an important stage of organizational growth.

Reporting directly to the Founder & CEO, this individual will build and manage a comprehensive development program that currently supports approximately $1.5 million in annual fundraising, with significant opportunity for growth.

This is a hands-on leadership role for someone who enjoys both strategy and execution. The Senior Director will cultivate and secure major gifts, expand foundation and institutional support, develop new donor relationships, lead donor engagement efforts, and build the systems and infrastructure necessary to support CPI's continued growth.

What You'll Do

• Develop and execute a comprehensive fundraising strategy across major gifts, individual giving, foundations, institutional funding, and corporate philanthropy.
• Build and manage a strong pipeline of donors and prospects, from identification and cultivation through solicitation and stewardship.
• Personally manage a portfolio of major donors and secure significant philanthropic investments.
• Partner closely with the Founder & CEO and Board on donor cultivation, fundraising strategy, and relationship development.
• Lead foundation and grant fundraising, including prospect research, proposal development, reporting, and relationship management.
• Develop compelling cases for support and donor communications that demonstrate CPI's mission, growth, and impact.
• Lead donor cultivation, stewardship, recognition, and fundraising events.
• Select and implement a donor CRM and establish effective development processes, reporting, analytics, and stewardship systems.
• Establish fundraising goals and metrics and provide regular development updates to leadership and the Board.
• Help build CPI's development team and capabilities as the organization grows.

What We're Looking For

• 10+ years of progressive fundraising experience, including leadership experience.
• A strong track record of fundraising success and building trusted relationships with donors and other stakeholders.
• An entrepreneurial, hands‑on leader who is equally comfortable setting strategy and executing the work.
• Experience working in a growing organization and building processes, systems, or programs from the ground up.
• Excellent communication and relationship‑building skills, with the ability to engage effectively with donors, executives, board members, and external partners.
• Strong organizational skills and the ability to manage multiple priorities in a fast‑moving environment.
• Strong experience with donor CRM systems.
• Bachelor's degree required.

Experience in higher education, workforce development, youth development, or a related field is preferred. Experience building a development function within a growing nonprofit and/or a CFRE credential is also a plus.

Compensation & Benefits

CPI offers a flexible hybrid work environment based in the Boston/Cambridge area, with approximately 20% travel for donor meetings, conferences, and organizational events.

• a healthcare stipend
• paid vacation and sick time
• paid holidays
• professional development support

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