Executive Administrative Assistant

Role overview

Boldly is recruiting remote executive administrative professionals for long-term placements across a range of sectors, such as nonprofit, finance, venture capital, technology, and casual fine dining. The company has operated entirely remotely from the start and is looking for experienced assistants who want flexible work while contributing meaningfully to the leaders they support.

As a Boldly employee, you will provide high-quality administrative support to executives at established Fortune 500 companies, nonprofits, senior leaders, and business owners. Assignments are matched based on your preferences and organizational values, and the work is designed to build lasting, productive partnerships.

Work arrangement

This is a 100% remote role with no night or weekend schedule. Full-time employees are expected to be available for 40 hours per week during business hours. The role is also referenced as available in part-time and full-time formats.

Key duties

• Keep executive calendars organized and appointments up to date
• Coordinate meetings, conferences, and business travel
• Book flights, hotels, and other travel arrangements
• Protect executive time by handling correspondence, drafting letters and documents, researching information, and placing calls on their behalf
• Oversee several executive email inboxes
• Track and manage expenses
• Support customers and suppliers as needed
• Handle additional executive administrative tasks as required

Candidate profile

Boldly is looking for a proactive, detail-focused, and adaptable executive assistant with a positive outlook and strong communication skills. The ideal candidate is comfortable working independently, learns new systems quickly, and thrives in a fast-moving environment. A strong sense of professionalism, flexibility, and a service mindset are essential.

The company emphasizes respect, kindness, transparency, flexibility, and inclusion. It also highlights support for military spouses, caregivers, parents, and others who need remote and flexible work arrangements.

Experience and skills needed

Applicants must have at least 7 years of direct, hands-on experience as an executive assistant or senior administrative assistant supporting one or more executives. General administrative work done as part of another role does not satisfy this requirement.

Candidates should be highly proficient with modern workplace tools and able to manage many priorities while maintaining strong organization, time management, writing quality, and interpersonal communication. The role also calls for independence, solution-oriented thinking, and comfort working under deadlines.

Compensation and benefits

The position pays $30 per hour and includes periodic pay increases over time. Full-time employees receive W2 employment status, employer-paid medical, dental, vision, and life insurance, a 401(k) with matching contributions, paid vacation and sick leave, paid holidays, paid parental leave, a technology stipend, and ongoing mentoring and support from a team leader.

Company culture and recognition

Boldly describes itself as a woman-owned, remote-first employer established in 2012, with a culture centered on belonging, diversity, equity, and inclusion. The company says it has been certified as a Great Place to Work for five consecutive years and has received recognition from Fortune, Entrepreneur, Color Magazine, Military Friendly, FlexJobs, and Flexa for workplace quality and flexibility.

Application notes

The company states that 7 years of executive assistant experience is the minimum requirement and that candidates without this background cannot be considered. It also expects applicants to maintain an up-to-date LinkedIn profile. Military spouses are especially encouraged to apply, and candidates should explain clearly in their resume how their experience aligns with the role’s requirements.