Senior Development Manager, Major Gifts

About Freedom Reads

Freedom Reads builds handcrafted wooden libraries for prison cellblocks across the country, placing curated collections of books directly in the spaces where incarcerated people live. Founded by MacArthur Fellow Reginald Dwayne Betts, Freedom Reads has installed more than 500 libraries in over 50 prisons across 15 states. We are entering a period of significant organizational growth, including preparation for a comprehensive campaign launching publicly in 2027.

Position Summary

The Senior Development Manager, Major Gifts, is a frontline fundraiser responsible for independently managing a portfolio of 75–100 individual donors and prospects, cultivating relationships, and making direct solicitations at the $25,000–$250,000 level. This position serves as a strategic thought partner to the Chief Development Officer on moves management, pipeline development, and campaign readiness. The Senior Development Manager also staffs the CDO and CEO for top-tier donor engagements while personally owning cultivation and solicitation across a significant portion of the individual giving portfolio.

This is a senior hire that requires independent judgment, comfort with high-value solicitations, and the ability to build lasting relationships with philanthropically motivated individuals. As Freedom Reads prepares for a major comprehensive campaign, this position will play a central role in building the donor pipeline and establishing the cultivation infrastructure needed for campaign success.

Essential Functions

Portfolio Management & Solicitation (50%)

• Manage a personal portfolio of 75–100 individual donors and prospects, maintaining active cultivation plans and regular contact cycles.
• Conduct independent solicitations for gifts and multi-year pledges ranging from $25,000 to $250,000, including developing ask strategies, preparing proposals, and closing gifts.
• Develop and execute individualized moves management plans for each assigned prospect, with clear milestones from identification through stewardship.
• Prepare donor briefing materials for CDO and CEO meetings, attend donor meetings as appropriate, and ensure timely follow-up on all action items.
• Track and report on portfolio activity, pipeline value, and progress toward annual and campaign fundraising goals.

Strategy & Campaign Support (25%)

• Serve as a strategic thought partner to the CDO on individual giving strategy, prospect prioritization, and pipeline analysis.
• Contribute to campaign planning activities, including prospect identification, rating and screening, gift range chart development, and feasibility assessment preparation.
• Collaborate with the CDO on board member engagement strategies, including supporting trustees in their fundraising activities and managing trustee prospect lists.
• Identify opportunities for donor cultivation events, parlor meetings, and site visits; manage logistics and follow-up for assigned events.

Stewardship & Donor Relations (15%)

• Design and execute personalized stewardship plans for major donors in the assigned portfolio, including impact reports, acknowledgment communications, and recognition opportunities.
• Coordinate with program staff to gather stories, data, and outcomes that support donor engagement and demonstrate impact.
• Ensure accurate and timely gift processing, acknowledgment, and documentation in the CRM system.

Team Collaboration & Operations (10%)

• Participate in development team meetings, pipeline reviews, and forecasting sessions.
• Mentor and support junior development staff as the team grows.
• Contribute to the development and refinement of fundraising systems, templates, and processes that support a scaling organization.

Required Qualifications

• Minimum 7 years of progressive development experience, with at least 4 years in a frontline major gifts fundraising role.
• Demonstrated track record of personally soliciting and closing five- and six-figure gifts from individual donors.
• Experience managing a portfolio of 50+ donors/prospects with documented cultivation and solicitation activity.
• Strong interpersonal skills and comfort engaging with high-net-worth individuals, executives, and board members.
• Excellent written and verbal communication skills, including the ability to produce compelling donor proposals, case statements, and briefing documents.
• Proficiency with CRM/donor management systems and moves management tracking.
• Ability to work independently, manage competing priorities, and exercise sound judgment with minimal supervision.
• Commitment to Freedom Reads’ mission and the belief that access to literature is a fundamental right.

Preferred Qualifications

• Experience in social justice, criminal justice reform, arts and culture, or education-focused organizations.
• Prior involvement in a comprehensive or capital campaign, including feasibility studies and campaign pipeline development.
• Experience working with or staffing a founder/CEO in donor meetings.
• Familiarity with prospect research tools and wealth screening platforms.
• Experience with multi-year pledge structures and planned giving conversations.

Compensation & Benefits

Compensation Range:

The salary range for this position is $100,000–$120,000, commensurate with experience. Freedom Reads offers a competitive benefits package. This position is available as hybrid (Hamden, CT headquarters) or fully remote for exceptional candidates.

Benefits:

• As a full-time employee, you will be eligible to participate in the employee benefit program
• offered by Freedom Reads as follows:
• Paid Time Off – 20 Days of PTO accrued throughout the calendar year, which will be prorated
• from your start date.
• Holiday Pay – 12 paid holidays per year.
• Health, dental, and vision benefits.
• $30 monthly phone stipend.
• Employer-paid Employee Assistance Program (EAP), life insurance, vision, and long-term disability
• coverage.
• Retirement plan with 3% employer-paid safe harbor contribution, beginning after the first 3 months of employment.
• Freedom Reads offices are closed between Christmas and New Year’s Day, inclusive.

To Apply

Please submit a resume and cover letter describing your major gifts fundraising experience, including specific examples of gift solicitations you have led and closed. Applications will be reviewed on a rolling basis.

• As a full-time employee, you will be eligible to participate in the employee benefit program
• offered by Freedom Reads as follows:
• Paid Time Off – 20 Days of PTO accrued throughout the calendar year, which will be prorated
• from your start date.
• Holiday Pay – 12 paid holidays per year.
• Health, dental, and vision benefits.
• $30 monthly phone stipend.
• Employer-paid Employee Assistance Program (EAP), life insurance, vision, and long-term disability
• coverage.
• Retirement plan with 3% employer-paid safe harbor contribution, beginning after the first 3 months of employment.
• Freedom Reads offices are closed between Christmas and New Year’s Day, inclusive.