Chief Administrative Officer

House of Possibilities Inc • Easton, MA

7h • $115,000 - $130,000

About The Position

We are seeking a strategic, collaborative, and operations-minded Chief Administrative Officer (CAO) to lead our administrative engine, ensure high-performing vendor partnerships, and empower our internal support team. Unlike traditional internal operational roles, the CAO at House of Possibilities oversees a modern, outsourced administration model. Rather than managing large in-house departments, you will drive strategy, service level agreement (SLA) performance, and compliance across our external service providers in Finance/Accounting, Human Resources, and IT. You will also directly manage and mentor our high-performing internal team, including a Contracts Specialist, HR Coordinator, and Administrative Support staff, ensuring our day-to-day infrastructure runs seamlessly in support of our mission.

Requirements

• Strategic, collaborative, and operations-minded leadership.
• Experience managing outsourced administration models.
• Proficiency in driving strategy, SLA performance, and compliance across external service providers (Finance/Accounting, HR, IT).
• Experience directly managing and mentoring internal teams.
• Knowledge of contract and grant governance, including state contracts, billing schedules, vendor agreements, and regulatory reporting.
• Experience in financial and budgetary coordination, including annual budgeting, financial analysis, audit preparations, and tax filings.
• Experience in facilities and risk management, including physical facilities, lease agreements, space planning, vendor maintenance contracts, and workplace safety protocols.
• Experience with IT and data compliance, including maintaining secure systems, technical support, and data privacy standards (e.g., HIPAA).

Responsibilities

• Serve as the primary relationship manager for outsourced partners across Finance, HR, and IT. Oversee contract performance, enforce SLAs, evaluate service quality, and drive cost-efficiencies.
• Directly supervise, coach, and support the internal administrative team (Contracts Specialist, HR Coordinator, and Administrative Support), fostering a supportive, high-accountability culture.
• Oversee state contracts, billing schedules, vendor agreements, and regulatory reporting in compliance with Massachusetts human services standards.
• Partner closely with our external accounting firm to facilitate annual budgeting, financial analysis, audit preparations, and tax filings.
• Manage physical facilities, lease agreements, space planning, vendor maintenance contracts, and workplace safety protocols.
• Collaborate with our outsourced IT provider to maintain secure systems, robust technical support, and strict compliance with data privacy standards (e.g., HIPAA).

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed