1099 Executive Assistant Jobs in Raleigh, NC (NOW HIRING)

Executive Assistant / Office Manager

AI Company, Cary, North Carolina (On-Site, Full-Time)

ABOUT THE ROLE

We're looking for an experienced Executive Assistant / Office Manager to support our CEO and help run our Cary, NC office. This is a hybrid role: part strategic right-hand to the CEO, part operational backbone of the office. It's built for someone with real seniority and judgment — not an entry-level administrative position.

You'll work in-office, alongside the CEO when he's on-site and independently managing the office and staff when he's traveling.

IMPORTANT — PLEASE READ BEFORE APPLYING

This is a full-time, on-site position in Cary, NC.

• 1099 Independent Contractor (not W-2)
• No remote work
• No hybrid work
• No relocation assistance
• Must already reside in the Raleigh-Durham-Cary area

Work Authorization

This is a 1099 Independent Contractor position.

• Employer sponsorship is not available
• US Citizens and Green Card / Permanent Residents are eligible
• TPS, U4U are eligible
• H-1B is not eligible, as it requires a W-2 employer-sponsor relationship
• The STEM OPT extension is not eligible, as it requires W-2 employment with an E-Verified employer

THIS ROLE IS NOT ENTRY-LEVEL

This position requires at least 10 years of experience as an Executive Assistant, Office Manager, or similar senior support role. Candidates without that depth of experience will not be considered — the role requires the maturity and judgment to work directly with a CEO and to manage staff and office operations independently.

WHAT YOU'LL OWN

1. Executive Time & Priority Management
2. Own the CEO's schedule to maximize his effectiveness — filtering out low-value distractions, protecting time for high-priority work, and making sure his time consistently goes to what matters most.
3. Strategic Project Management
4. Help drive the company's strategic objectives forward by learning and implementing the CEO's execution methodology across the leadership team. You'll be responsible for making sure every manager and executive is actually following the process — not just aware of it.
5. Staff Communication & Meeting Readiness
6. Be a trusted point of contact for staff — listening to problems, helping resolve what you can, and escalating what you can't. You'll coach staff on how to prepare for meetings with the CEO and how to run those meetings effectively, so his time with them is high-value.
7. Communication Bridge / Content Creation
8. Sit in on meetings, understand the CEO's intent from notes and conversations, and translate that into clear communication for the team — effectively serving as the bridge between the CEO and staff.
9. Travel & Logistics
10. Handle all travel arrangements — flights, car rentals, points/upgrades, itineraries — with genuine creative problem-solving, not just booking the first available option. AI tools are welcome and encouraged for these tasks.
11. Office Management & Admin
12. Run the day-to-day business of the Cary office: benefits and health insurance administration, payroll support, facilities, working with the accountant to keep filings and business documents current, and general office administration.

WHAT WE'RE LOOKING FOR

• 10+ years of experience as an Executive Assistant, Office Manager, or similar senior support role.
• Genuine maturity and professionalism — comfortable working closely with a CEO and other senior executives, and comfortable managing staff independently.
• Experience with basic business operations in the US: payroll, benefits and health insurance administration, and working with an accountant on filings and compliance documents.
• Strong, creative problem-solving skills, especially around travel logistics.
• Comfortable using AI tools to support day-to-day tasks.
• Excellent communication skills — able to translate a CEO's intent into clear guidance for a team, and able to coach others on effective communication.
• Speaking Ukrainian is a plus.

WORK ARRANGEMENT

• Contract Type: 1099 Independent Contractor
• Schedule: Full-Time Hours
• Location: On-Site — Cary, NC (remote and hybrid are NOT available)
• Compensation: $50,000 per year
• Experience: 10+ years

You'll be in the office consistently, including when the CEO is traveling — at those times, you're responsible for keeping an eye on staff and keeping office operations running.

HIRING PROCESS

1. Apply on Indeed
2. Complete a 35-45 minute online assessment
3. Video interview
4. Final interview with the CEO

HOW TO APPLY

After submitting your resume, you will receive a link to a screening assessment (35-45 minutes). Candidates who complete the assessment are prioritized for review.

Direct assessment link: https://forms.gle/djb26qefNtt9UUjj8

Please complete the assessment within 48 hours to keep your application active.

Pay: $48,000.00 - $50,000.00 per year

• Work Location: In person