Chief Administrative Officer

Chief Administrative Officer (CAO)

Reports To

President and Chief Executive Officer

Location

Portland, ME (on-site- relocation assistance provided)

FLSA Status

Exempt

Department

Executive / Administration

Position Summary

The Chief Administrative Officer (CAO) leads people operations and provides leadership, coaching, and cross-functional alignment to the Technology, Client Services, and Accounting functions. This role gives the President and CEO a trusted partner who helps these functions operate in an aligned, disciplined way as the company scales to support roughly 120 employees serving regulated clients in healthcare and financial services markets.

Key Responsibilities

Human Resources & People Operations

• Own HR strategy, policy, and programs: recruiting support, onboarding, performance management, compensation administration, and employee relations.
• Ensure compliance with federal, Maine, and applicable multi-state employment law.
• Partner with department leaders on workforce planning, staffing levels, and organizational design.
• Oversee benefits administration, broker relationships, and annual open enrollment.
• Own HRIS and related people-systems administration.

Leadership & Coaching of Key Functional Leaders

Vendor & Procurement Management

• Own non-production vendor relationships and procurement processes.
• Negotiate and manage contracts for administrative services (insurance, benefits brokers, office vendors, professional services).
• Monitor vendor performance, costs, and renewal timelines.

Cross-Functional Systems & Process Administration

• Serve as executive owner for administrative governance of business systems (NetSuite, HubSpot, Jira/Tempo), ensuring processes and access controls support the business.
• Standardize administrative processes and reporting across the company.
• Identify and lead process-improvement initiatives as the company scales.

Executive Partnership

• Serve as a trusted advisor to the President and CEO on organizational, people, and administrative matters.
• Represent the administrative function in leadership meetings and planning.
• Lead special projects and initiatives as assigned by the President and CEO.

Qualifications

• Bachelor's degree in Accounting, Finance, Business Administration, or a related field; MBA or relevant advanced degree a plus.
• 10 years of progressive leadership experience spanning finance and general management
• Demonstrated track record as a CFO for a small to mid sized company or senior financial leader, ideally including experience leading finance and administration across multiple related or affiliated entities simultaneously.
• Experience in manufacturing, production, or other operationally intensive environments, and comfort operating in regulated or high-scrutiny industries (healthcare, financial services, or similarly mission-critical sectors) — including through periods of rapid growth or crisis — both strong pluses.
• Demonstrated experience coaching and aligning a cross-functional group of leaders — including technology, client services, and finance/accounting — without formal line authority over them.
• Strong grounding in HR practices, employee relations, and applicable employment law.
• Experience with business systems such as NetSuite, HubSpot, and Jira/Tempo (or comparable ERP/CRM/PM tools) a plus.
• Exceptional judgment and discretion; comfortable operating with a high degree of autonomy.
• Strong written and verbal communication skills; ability to influence and align diverse functional leaders.
• CPA, CFA, or equivalent finance credential a plus.

Core Competencies

• Strategic and operational thinking
• Discretion and integrity handling sensitive information
• Change management and process improvement
• Cross-functional collaboration
• People leadership and team development
• Resilience and sound judgment under pressure, ambiguity, or rapid change