Executive Assistant to Executive Director/Owner (Hybrid) HCBS In-Home Service Agency

T&T Cares•Boring, OR

6d•Hybrid

About The Position

T&T Cares LLC is a Medicaid-licensed Home and Community-Based Services (HCBS) agency providing Community Living Supports to individuals with intellectual and developmental disabilities across Oregon under ODDS/ODHS. Operating on a consumer-directed service model, the agency maintains a strong commitment to regulatory compliance, audit readiness, and durable internal systems that protect the individuals we serve, our workforce, and the integrity of our services. T&T Cares is seeking a highly capable Executive Assistant to provide comprehensive, confidential support to the Owner and Executive Director. This is a high-trust, high-autonomy position designed to extend the Director's capacity across the full range of executive responsibilities — operational, administrative, regulatory, and personal. The Executive Assistant serves as the primary point of coordination for the Director's calendar, correspondence, project pipeline, and stakeholder communications. Because the Director is an owner-operator whose professional and personal commitments are closely intertwined, this position includes coordinated management of both professional and personal scheduling. Discretion across both domains is essential. The position is hybrid in nature: primarily remote, with periodic in-state travel for client visits, staff meetings, training sessions, conferences, and engagements with state agencies. This role is best suited to a candidate who exercises sound independent judgment, maintains the highest standards of professionalism and confidentiality, and is energized by variety and ownership rather than narrowly defined scope.

Requirements

Minimum of three years of executive, administrative, or operations support experience, preferably in direct support of a founder, owner, or senior executive.
Excellent written and verbal communication skills.
Demonstrated organizational, prioritization, and project management capabilities.
High level of discretion, judgment, and professionalism in handling confidential matters.
Proficiency with Google Workspace, Microsoft Office, DocuSign, and cloud-based document management systems.
Willingness and capacity to learn agency-specific platforms, including eXPRS, Therap, Paychex Flex, Blaze, and JotForm.
Oregon residency, valid driver's license, reliable transportation, and current auto insurance.
Ability to travel periodically within Oregon.
Successful completion of a criminal background check and Oregon abuse registry clearance, as required for HCBS-affiliated personnel.
Dedicated home office environment suitable for confidential work, including high-speed internet and secure handling of PHI.

Nice To Haves

Prior experience within an HCBS, Medicaid, healthcare, social services, or nonprofit setting.
Familiarity with Oregon ODDS/ODHS programs, OAR compliance, or services for individuals with intellectual and developmental disabilities.
Experience supporting executives in regulated or compliance-driven industries.
Comfort working within a small, owner-led organization in which responsibilities evolve alongside the needs of the business.

Responsibilities

Manage the Director's professional and personal calendars, ensuring alignment across business priorities and personal commitments.
Triage incoming communications, identify items requiring the Director's attention, and respond directly to matters within scope.
Prepare meeting materials, agendas, briefings, and follow-up summaries.
Maintain the Director's task list and proactively surface priorities, deadlines, and dependencies.
Draft, format, and finalize professional correspondence, internal memoranda, formal letters to state agencies, HR documentation, and policy materials.
Maintain consistency of voice and presentation across all communications issued under the Director's name.
Support document execution and records management through DocuSign, JotForm, Dropbox, and Blaze.
Serve as a liaison among internal departments — Human Resources, Payroll and Billing, Client Supports, and Administration — to advance executive priorities.
Coordinate with external stakeholders, including case managers, CDDPs, state agencies, vendors, and partner organizations.
Monitor regulatory deadlines, credential renewals, training requirements, and other time-sensitive obligations.
Arrange in-state travel, accommodations, and itineraries.
Coordinate logistics for personal commitments that intersect with the Director's professional availability.
Provide on-site support at meetings or events as required.
Handle protected health information (PHI), personnel records, investigation files, and sensitive personal matters in strict accordance with HIPAA and agency policy.
Maintain confidentiality across all professional and personal matters encountered in the course of this role.