Executive Assistant to Founder | AI-Driven Ops & Scheduling

Inside Out Hiring; United States; Remote; USD 28,000 - 33,000; Full time

Job summary

Inside Out Hiring seeks an Executive Assistant to support the founder across a multi-location dental practice group. You will own day-to-day administration, manage emails, calendar scheduling, and follow-ups while organizing vendor and policy documentation for scalable operations.

You will use Claude for AI-driven workflows, dashboards, and automation, providing clear daily updates and facilitating communication with managers and staff as the role expands.

Qualifications

• Prior experience working as an Executive Assistant or Chief of Staff supporting a senior executive or founder is required.
• Fluent written and verbal English communication skills, with the ability to interact professionally and clearly with the executive and staff.
• Experience using or training on AI tools such as Claude for email management, workflow automation, and dashboard creation, or strong aptitude and willingness to be trained on these tools.
• Operations experience is a plus, as the role may expand to include light operations support over time.
• Demonstrated ability to work independently, exercise sound judgment and proactively surface priorities without close supervision.
• Strong organizational skills with experience managing detailed records such as policy or vendor documentation.

Responsibilities

• Calendar & Scheduling: Manage the executive's calendar across platforms, schedule meetings, and send reminders to keep commitments on track.
• Inbox Management: Triage incoming email, draft responses, flag priority items, and ensure timely follow-up on outstanding threads.
• Vendor & Policy Administration: Organize and maintain records such as insurance policies and vendor agreements, tracking renewal dates, costs, and payment requirements in a structured format.
• Task Follow-Up: Track action items delegated by the executive, follow up with staff or external parties, and report status proactively.
• AI-Enabled Workflow Support: Use Claude and related tools to build dashboards, automate repetitive processes, and organize information for easier executive decision-making.
• Executive Reporting: Provide structured start-of-day and end-of-day updates summarizing priorities, progress, and blockers.
• Cross-Team Coordination: Liaise with managers and administrative staff to gather information and support delegated projects as the role expands.

Skills

Executive support

English proficiency

AI tools (Claude)

Operations experience

Independent work

Organizational skills

Tools

Claude AI

Gmail / Calendar apps

Google Meet

Spreadsheet & dashboards

Job description

Inside Out Hiring seeks an Executive Assistant to support the founder across a multi-location dental practice group. You will own day-to-day administration, manage emails, calendar scheduling, and follow-ups while organizing vendor and policy documentation for scalable operations.

You will use Claude for AI-driven workflows, dashboards, and automation, providing clear daily updates and facilitating communication with managers and staff as the role expands.