Executive Director

The Caleb Group Seeks Executive Director

Founded in 1992, The Caleb Group (“Caleb”) is a regional nonprofit affordable housing organization that acquires, develops, preserves, and manages service-enriched affordable housing for households with low to moderate incomes. Through the efforts of on-site service coordinators, its intentional programming, and the community centers associated with each property, Caleb strives to create positive, supportive, and encouraging communities where residents are offered the resources and programs needed to help stabilize and improve their lives. 

Currently overseeing 1,300 affordable housing units in more than 34 communities in Maine, New Hampshire, Massachusetts, and Connecticut and guided by its 2023-25 strategic plan, Caleb has been overseen by the Sawyer family since it was founded by Warren, Joan, and Debbie Sawyer. Having transitioned to an external interim leader since Debbie Sawyer’s retirement as Executive Director in June 2024, Caleb is now poised to hire a permanent external leader. More information on Caleb’s history can be found here, and a list of the communities served can be located here. 

Operating out of its headquarters in Lynn, MA, Caleb has a geographically dispersed staff of 75 and an annual operating budget of approximately $25 million, inclusive of property management expenses. Caleb is overseen by a 10-member Board of Directors comprised of industry and community leaders, some of whom have long histories with the organization.

Opportunity Going Forward 

The Executive Director will have the opportunity to lead a well-established and -respected mission-driven organization with deep roots and strong partnerships throughout New England. Guided by its belief that a clean, safe living environment is integral to a stable life and a positive, supportive factor in helping people thrive, key responsibilities for the Executive Director include: 

• Navigating the transition from a family-led nonprofit to one that is externally led ensuring that existing strong relationships with partners, collaborators, lenders, and government officials are maintained and grown.
• Strengthening partnerships with other housing organizations, landowners, and political entities to continue to position Caleb as a go-to New England developer during a time when housing is a key local, state, and national priority.
• Collaborating with the Board of Directors to complete the implementation of the 2023-25 strategic plan, refine impact measurements particularly regarding resident services, recruit additional board members, strike the right balance between governance and management, and shepherd the organization through development of its next strategic plan.
• Evaluating Caleb's overall financial health and regularly communicating this to the Board along with information regarding the long-term cash flow projections for each property.
• Upgrading, professionalizing, and modernizing its internal operations, systems, processes, and technology and to improve staff efficiency and customer service.
• Actualizing an organizational structure that maximizes staff contributions and enhances organization-wide collaboration to achieve project goals in a professional, efficient, and mission-driven environment.
• Championing the implementation of human resource strategies to recruit, onboard, and retain high-quality staff willing to make long-term commitments to Caleb. 

• Improving communication protocols and processes so all Caleb staff members are well-informed and empowered to contribute to Caleb’s success.

   

Profile of the Ideal Candidate

Preferred Experience:

• A minimum of seven years of senior leadership, or equivalent experience, with a preference for those who have led an organization focused on housing and/or real estate development, with an emphasis on affordability. 
• Knowledge of and passion for real estate, community, and/or economic development.
• Exposure to the New England housing market would be advantageous.

Skills and Qualities:

Visionary and Strategic Change Agent with Industry and Financial Expertise

• Visionary and strategic thinker with the ability to see the big picture, and, when required, be a change agent willing to recommend needed reforms while respecting the organization’s history.
• Charismatic and energetic with the ability to inspire excitement and drive participation.
• Strong financial acumen and understanding of the complexities of real estate development and affordable housing finance, specifically LIHTC.
• Systems thinker with a business-like mentality who can balance risk-taking with long-term sustainability.          

Experienced Leader of People and Culture

• A compassionate, fair, approachable, and supportive leader, a skilled listener who can create a work culture that is humane and collaborative across all teams and who can implement human resource best practices. 
• Skilled at evaluating and creating an organizational structure that is firm, yet fluid, to allow Caleb to support past growth and consider new opportunities. 
• Expert teambuilder able lead a diverse group of professionals working together on all aspects of the Caleb Mission including development, resident services, construction, asset management and finance.
• Experienced in hiring, onboarding, overseeing, motivating, and developing professional staff.
• Strong leadership acumen with experience activating and empowering a strong senior leadership team to collectively foster a culture where all staff are held to high and equal levels of accountability. 
• Experience growing and sustaining a strong Board of Directors.

Networker and Relationship Builder with Excellent Communication Skills

• Nonpartisan networker able to build strong and lasting relationships with lenders, partners, landowners, etc. and demonstrate the political and negotiation skills needed to advance Caleb’s strategic initiatives.
• A skilled public spokesperson with the ability to engage others and to tell Caleb’s unique story.
• A present and accessible leader to stakeholders in existing Caleb communities to understand, reflect on, and meet residents’ needs and in new locations to promote future development opportunities. 
• Transparent and open-minded communicator, both internally and externally, with a willingness to listen and engage diverse audiences.

Compensation and Benefits:

This is a full-time, salaried, exempt position with a starting salary range of $190,000 to $220,000, commensurate with experience and qualifications. Caleb also offers a comprehensive and generous benefits package which includes health, dental, vision, group life and disability insurances, health savings accounts, a retirement plan, and generous time off. Caleb will consider a variety of hybrid work scenarios.