Executive Assistant

Role overview

Boldly is seeking experienced executive assistants for remote part-time and full-time opportunities. The company supports leaders across nonprofit, finance, venture capital, technology, and upscale dining environments, and works with Fortune 500 organizations, nonprofit teams, senior executives, and business owners. This is a long-term remote role designed for professionals who want flexible work and meaningful client partnerships.

This position has been fully remote from the start. Work is structured around regular business hours, with no evening or weekend shifts.

Key responsibilities

The executive assistant will provide high-level administrative support and help executives stay organized, responsive, and efficient. Duties may include calendar management, meeting coordination, travel planning, inbox management, expense tracking, and communication support.

• Keep schedules and calendars organized and up to date
• Arrange meetings, conferences, and travel logistics
• Book flights, hotels, and related travel items
• Protect the executive’s time by handling correspondence, drafting documents, researching information, and placing calls on their behalf
• Oversee multiple executive email inboxes
• Track and manage expenses
• Assist with customer and supplier communication
• Handle additional executive administration tasks as needed

Candidate profile

Applicants should bring deep senior-level administrative experience and be comfortable supporting several high-level leaders in a fast-moving environment. The ideal candidate is proactive, adaptable, highly organized, technology confident, and committed to delivering excellent work with a positive and collaborative attitude.

Boldly values flexibility, respect, kindness, transparency, and a workplace culture where team members can thrive while balancing personal responsibilities.

Required experience and skills

• At least 7 years of direct, hands-on experience in a role such as executive assistant, virtual assistant, or senior administrative assistant
• Previous senior administrative support experience in a fast-paced setting with multiple executives
• Strong proficiency with Google Workspace, Office 365, Zoom, and similar productivity tools
• Ability to manage multiple priorities and switch tasks efficiently
• Excellent organization and time management abilities
• Quick to learn new systems and tools
• Strong interpersonal and written communication skills
• Comfort working independently and meeting deadlines under pressure
• Analytical, solution-focused mindset

Compensation and benefits

The hourly pay rate is $30, with regular pay increases over time. Total compensation also includes benefits such as employer-matched 401(k) coverage.

• W-2 employee status
• 100% remote work
• Flexible scheduling within normal business hours
• Part-time work starting at 20 hours per week, with the option to remain part-time or move to full-time
• 401(k) with employer match
• Paid time off, including vacation, sick leave, holidays, and parental leave
• Technology stipend
• Wellness events
• Ongoing coaching and support from a team leader

About the company culture

Boldly is a woman-owned, remote-first company founded in 2012. Its team includes parents, military spouses, caregivers, and others who value flexible work arrangements. The company emphasizes inclusion, belonging, and a supportive environment where people can build rewarding careers without sacrificing personal commitments.

The organization has been recognized as a Great Place to Work for five consecutive years and has received honors from Fortune, Entrepreneur, Color Magazine, Military Friendly, FlexJobs, and Flexa.

Additional information

The company is hiring for multiple part-time and full-time roles across several industries, including nonprofit, finance, venture capital, technology, and casual fine dining.