Project Place Director of Social Enterprise

About Project Place

Project Place promotes a community of hope and opportunity for homeless and low-income individuals by providing the skills, education and resources needed to obtain and sustain employment and housing. For over 50 years, Project Place has been a resource for individuals who are experiencing homelessness in Boston. Through innovative programming, including social enterprises, we facilitate individuals' successful transition to economic self-sufficiency. Comprehensive programming consists of classroom instruction, credentialing, case management services, housing and job placement, retention, and employment services.

About This Role

As Director of Social Enterprise, you will hold one of the most mission-critical roles at Project Place—serving as both a business leader and a champion for client transformation. This position sits at the very heart of our work: creating dignified pathways to employment for individuals facing homelessness and barriers to opportunity. Every day, you will witness firsthand how meaningful work changes lives, as our clients build confidence, develop professional skills, and take steps toward economic stability through our employment social enterprise. .

Your success in this role will directly determine the futures of dozens of individuals each year. You will lead businesses that are not just revenue generators, but transformational spaces where people who have been excluded from the workplace discover their own capability and worth. The relationships you build with corporate and government partners will create opportunities for our clients. The operational decisions you make will ensure quality training experiences. The team you develop will include graduates of our programs who return as mentors and supervisors, embodying the long-term impact of this work.

This is a role for someone who sees business as a vehicle for social change—who understands that financial sustainability and human dignity are not competing priorities, but rather interdependent goals. You will need entrepreneurial skills and business acumen to ensure our enterprises thrive financially. But what will make you successful here is a deep, unshakeable commitment to the belief that every person deserves a chance to experience financial mobility through meaningful work.

You will lead Project Place's entire social enterprise portfolio—overseeing revenue-generating businesses that provide on-the-job training and skill development while contributing to organizational sustainability. Working as a key member of our Senior Leadership Team, you will develop growth strategies, cultivate partnerships, manage operations across multiple business lines, and ensure seamless integration with our education and reentry programs. Your ability to balance our dual bottom line—profitability and participant success—will be fundamental to Project Place's impact and long-term sustainability.

A Note About Leadership Transition

The Director of Social Enterprise will initially report to the Director of Finance and Social Enterprises. Over the coming year, as the current Director transitions toward retirement, you will shift to reporting directly to the Executive Director. This transition period will provide valuable institutional knowledge and relationship continuity while you assume full operational authority from day one.

What You'll Do

Strategic Leadership, Business Development & Sales

• Develop and implement comprehensive multi-year social enterprise growth strategy aligned with Project Place's mission
• Personally drive business development and sales efforts to grow customer base and generate revenue
• Build and maintain strategic relationships with private sector businesses, corporate partners, and institutional customers through direct engagement
• Cultivate and manage relationships with city and state government contacts to secure contracts and expand public sector partnerships
• Identify, evaluate, and launch new social enterprise opportunities that advance both financial sustainability and participant impact with the goal of increasing skills developed and number of clients served
• Represent Project Place at industry conferences, business networking events, and community forums
• Develop compelling sales proposals and presentations that communicate the value proposition of our social enterprises
• Serve as a member of the Senior Leadership Team, supporting organizational growth aligned with mission, vision, and values

Program and Business Operations

• Oversee daily operations of all social enterprises, ensuring operational efficiency, high-quality service delivery, and financial performance
• Directly supervise Social Enterprise Directors providing coaching and performance management
• Partner closely with other departments to ensure seamless integration of training and support services
• Establish and enforce quality standards, operational procedures, and customer service protocols
• Ensure enterprises provide meaningful work experiences that build client skills, confidence, and employment readiness
• Manage relationships with a team that includes Project Place program graduates serving in supervisory and mentorship roles

Financial Management & Accountability

• Lead budgeting, forecasting, and financial planning processes for all enterprise activities
• Manage profit and loss (P&L) for each social enterprise line, ensuring financial sustainability and revenue growth
• Monitor financial performance proactively and implement corrective actions—raising concerns before they become problems
• Develop pricing strategies, cost structures, and financial models for existing and new ventures
• Track key financial metrics including gross margin, operational costs, and revenue per client
• Present regular financial reports to Senior Leadership Team and Board of Directors
• Think strategically about how enterprise revenue supports the organization's overall sustainability

Team Development & Supervision

• Build and lead a high-performing team, providing direct supervision to enterprise directors
• Recruit, hire, train, and develop staff committed to both business excellence and social mission
• Make decisive personnel decisions when team members are not meeting expectations
• Model a culture of innovation, collaboration, and mission-driven business practice
• Build staff capacity through teaching—help team members understand concepts like gross margin, pricing strategy, and financial decision-making
• Work effectively with team members who are industry experts and bring lived experience, recognizing they may have different educational backgrounds but tremendous field knowledge

Measurement, Evaluation & Impact Reporting

• Establish and track key performance metrics for both financial outcomes and social impact results
• Use data insights to drive continuous improvement and optimize business and program performance
• Monitor grant deliverables proactively and problem-solve when targets are at risk
• Prepare compelling impact reports demonstrating the value and effectiveness of our social enterprise model
• Track and manage client wage budgets and operational expenses

Qualifications

There are innumerable ways to learn, grow, and excel professionally. We respect this when we review applications and take a broad look at the experience of each applicant. We want to get to know you and the unique strengths you will bring to the work. This said, we are most likely to be interested in your candidacy if you can demonstrate the majority of the qualifications and experiences listed below.

Required

• 7+ years of progressive experience in business operations, entrepreneurship, or social enterprise management
• Deep commitment to social justice and the ability to balance business performance with participant development and dignity
• Demonstrated success in business development, sales, or partnership cultivation—you must have a proven track record of identifying and securing new business
• Proven success managing profit or loss (P&L) or revenue-generating ventures with accountability for financial performance
• Strong analytical skills, including budgeting, forecasting, financial analysis, and understanding of key business metrics
• Analytical mindset and comfort with data-driven decision-making
• Experience managing teams and providing direct supervision to multiple reports
• Excellent leadership, communication, and strategic planning skills
• Ability to build relationships across diverse stakeholder groups—from corporate executives to government officials to frontline staff to clients with lived experience
• Entrepreneurial mindset with ability to identify opportunities, take calculated risks, and drive innovation
• Comfort with change, ability to pivot quickly, and resilience in an entrepreneurial nonprofit environment

Preferred

• Experience in social enterprise, transitional employment, or mission-driven business environments
• Experience in nonprofit operations that function like a business (e.g., logistics including warehouse and delivery operations, food service, outdoor cleaning and janitorial services)
• Knowledge of workforce development, transitional employment, or job training programs
• Experience working with individuals experiencing homelessness, barriers to employment, or involvement in the justice system
• Familiarity with government contracting processes and public sector partnerships
• Track record of launching or scaling new business ventures or product lines
• Comfort teaching and developing others—ability to translate complex business concepts into understandable lessons for staff and clients

Compensation & Benefits

The salary range for this position is $95,000 to $110,000 and is commensurate with experience. Project Place offers a comprehensive benefits package that includes:

• Health insurance (vision & dental), and life and long-term disability insurance
• 401k plan with employer match
• Paid time off, beginning at 3 weeks per year in the first year of employment
• Professional development opportunities

Work Environment

This position is full-time with availability for occasional evening and weekend work and is located at Project Place Headquarters in the South End neighborhood of Boston. The role requires 4 days per week in the office, with flexibility for remote work one day per week. This role also requires regular presence at enterprise work sites to maintain connection with operations and staff.

Timeline and Hiring Process

We will review and respond to all applications received. Candidates elected to advance through the process can expect:

• Initial screening with Positively Partners
• Hiring manager interview with the current Director of Social Enterprises and the Executive Director
• Business strategy presentation or exercise with senior program leadership
• In-person interview day including senior leadership panel and meet-and-greet with direct reports
• Comprehensive reference check process

Expected start date is late January/early February 2026.

How to Apply

To apply for this position, please submit a resume and thoughtfully written cover letter through our online portal. We will review and respond to all applications received. In your cover letter, please specifically address your experience with business development/sales and your understanding of or experience with social enterprise or mission-driven business models. For confidential inquiries or assistance completing the application, please contact mcarlton@positivelypartners.org.

Equal Opportunity Statement

Project Place is an equal opportunity employer and we encourage candidates of color, women, LGBTQ+, low-income, and non-college degree holders to apply. Project Place prohibits unlawful discrimination against any employee or applicant for employment based on race, color, religion, sex, gender identity, age, national origin, genetic characteristics, disability, status as a special disabled veteran or veteran, marital status, sexual orientation, sexual identity or any other basis prohibited by law.

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