Remote Executive Assistant & Ops Partner (AI-Savvy)

Inside Out Hiring

United States

Remote

USD 22,000 - 28,000

Full time

14 days+

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Job summary

Inside Out Hiring is seeking a proactive Executive Assistant to serve as the operational right-hand partner for a veteran entrepreneur. This remote role supports a Wisconsin-based leader from LATAM or South Africa, handling digital transformation, research, and communications.

You will leverage Claude and other AI tools to turn handwritten notes into structured workflows, draft collateral, and enable projects to move smoothly. Fluency in English and 3+ years of executive support are required.

Qualifications

3+ years as an Executive Assistant or similar supporting founders or C-suite.
Flawless written and spoken English with strong prioritization and time-management.
Strong proficiency with AI tools, especially Claude, for research and workflow development.
Highly proactive, self-directed, organized, and capable of guiding a traditional business into digital workflows.

Responsibilities

Manage executive workflow and priorities; maintain task lists and follow-up systems.
Coordinate operations and follow-ups with vendors, contractors, and partners; assist with project quotes.
Conduct AI-assisted research and draft communications, SOPs, and dashboards.
Coordinate personal appointments and family logistics to reduce mental load for the owner.
Document SOPs, build repeatable processes, and identify operational efficiencies.