5-10 years of experience in administrative leadership roles
Proven track record of managing outsourced service providers
Strong background in compliance and regulatory reporting
Experience with financial management and budgeting
Excellent team leadership and coaching abilities
Responsibilities
Serve as primary manager for outsourced finance, HR, and IT partners
Supervise and coach internal administrative team to ensure high performance
Oversee compliance with state contracts and billing schedules
Coordinate annual budgeting and financial analysis with accounting firms
Manage physical facilities and ensure workplace safety protocols
Collaborate with IT provider on data privacy and technical support
Benefits
Flexible work arrangements
Opportunities for professional development
Supportive work culture focused on accountability
Access to health and wellness resources
Engagement with a mission-driven team
Full Job Description
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.
Key Responsibilities
Vendor & SLA Management: 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.
Team Leadership & Coaching: Directly supervise, coach, and support the internal administrative team (Contracts Specialist, HR Coordinator, and Administrative Support), fostering a supportive, high-accountability culture.
Contract & Grant Governance: Oversee state contracts, billing schedules, vendor agreements, and regulatory reporting in compliance with Massachusetts human services standards.
Financial & Budgetary Coordination: Partner closely with our external accounting firm to facilitate annual budgeting, financial analysis, audit preparations, and tax filings.
Facilities & Risk Management: Manage physical facilities, lease agreements, space planning, vendor maintenance contracts, and workplace safety protocols.
IT & Data Compliance: Collaborate with our outsourced IT provider to maintain secure systems, robust technical support, and strict compliance with data privacy standards (e.g., HIPAA).
