Deputy Director

About Central Square BID

The Central Square Business Improvement District (CSBID) is a 501(c)(3) nonprofit organization established in 2019 to enhance, promote, and support the Central Square Cultural District in Cambridge, MA. We strengthen Central Square through clean and safe services, public realm management, placemaking, economic development, and deep community partnerships.

Position Summary

The Deputy Director / COO is a senior executive responsible for the operational health, financial stability, and internal organizational systems of CSBID. Reporting directly to the Executive Director, the Deputy Director oversees daily operations, manages resources and cross-departmental projects, and translates strategic priorities into executable plans. This role is being established to strengthen operational systems, improve organizational efficiency, and support the organization's long-term financial sustainability as CSBID grows.

The ideal candidate is highly organized, proactive, and detail-oriented — someone who balances strategic thinking with hands-on execution and brings strong communication, financial acumen, and genuine energy to the work.

Key Responsibilities

Operational Leadership & Execution

• Oversee day-to-day operations of the organization, ensuring reliability, clarity, and accountability
• Develop and refine operational systems, workflows, and standard operating procedures
• Lead planning and coordination across departments to ensure commitments are delivered on

time and within budget

• Partner with the Executive Director to align operational execution with strategic priorities
• Act as Executive Director in their absence

Financial Management & Discipline

• Lead the annual budget process from planning through execution and reporting
• Oversee monthly financial tracking, forecasting, and variance analysis
• Strengthen financial discipline to reduce surprises, reinforce sustainability, and protect reserves
• Identify opportunities to optimize costs, strengthen margins, and expand diversified revenue

streams

• Lead planning and management of the annual financial audit and budget formulation
• Ensure sound internal controls, account reconciliations, and compliance across all financial

operations

• Supervise accounts payable, accounts receivable, cash management, and grant-related financial functions

Team & Organizational Leadership

• Supervise staff and contractors across departments, ensuring clarity of roles and performance

expectations

• Strengthen performance management systems to support staff development and

accountability

• Conduct regular supervision meetings and annual performance reviews
• Improve internal communications, collaboration, and organizational alignment
• Support recruitment, onboarding, and training in partnership with the Executive Director

Project Prioritization & Capacity Management

• Maintain and oversee the organization's master project plan, aligning initiatives with realistic

timelines and organizational capacity

• Assess organizational readiness before launching new initiatives
• Promote execution discipline — ensuring existing commitments are delivered before additional expansion is pursued

Institutionalization & Risk Management

• Strengthen internal documentation, knowledge systems, and operational redundancy to reduce organizational risk
• Support compliance across contracts, grants, HR, insurance, and reporting requirements
• Increase organizational resilience during personnel transitions and unexpected events

Board Operations, Governance & Executive Support

• Serve as the primary internal lead for board operations, governance systems, and executive support
• Partner with the Executive Director and Board leadership to maintain a clear annual governance calendar — meetings, committee cycles, audits, budgets, and strategic milestones
• Prepare and coordinate board materials, dashboards, and financial reports in a consistent and

professional format

• Support board committees — Finance, Governance, and others — with agendas, follow-up, and execution tracking
• Ensure board decisions are translated into clear internal priorities and operational follow-through
• Strengthen compliance with bylaws, policies, and governance best practices

Qualifications & Experience

Required

• 8+ years of progressive operational leadership — ideally in nonprofits, BIDs, municipal partnerships, or complex civic organizations
• Demonstrated track record managing budgets, finances, and operational systems with real dollar accountability
• Strong project management and organizational design skills
• Experience supervising teams and improving internal processes
• Proficiency with Salesforce or comparable CRM/task management systems

Preferred

• Experience leading operations in a BID, city agency, CDC, urban planning organization, or similar institution
• Comfort with financial forecasting, performance dashboards, and board reporting
• Ability to work collaboratively with external stakeholders — municipal partners, boards, and funders

Compensation & Benefits

Salary range: $120,000 – $135,000

Performance incentive program available for exceptional results.

• 100% employer-paid individual health insurance with partial dependent coverage
• Dental and vision coverage
• 3–4 weeks PTO plus sick time and standard holidays
• $2,000–$5,000 annual professional development budget — IDA, conferences, coaching, executive development

How to Apply

Application deadline: Tuesday April 21st, 2026 at 5:00 PM — no extensions.

Send the following to hello@centralsq.org:

• Resume — PDF preferred
• Cover letter — tell us specifically why this role and why Central Square BID

We will acknowledge all applications and move quickly. First-round screening calls begin the week of April 28th.

No phone calls please. Email hello@centralsq.org for all questions.

100% employer-paid individual health insurance with partial dependent coverage

• Dental and vision coverage
• 3–4 weeks PTO plus sick time and standard holidays
• $2,000–$5,000 annual professional development budget — IDA, conferences, coaching, executive development

English