Executive Assistant; Remote

If you're a career Executive Assistant who brings expertise, care, and genuine enthusiasm to your work — and you're ready for a remote role that respects both your talent and your life — we'd love to meet you.

We’re hiring experienced Executive Assistants who are ready to match their high-level skills with a role that gives them the flexibility to prioritize what matters most in their lives, without ever worrying about being called back into an office.

As a Boldly team member, you'll be a W2 employee supporting one or more executives in long-term partnerships and becoming a trusted strategic partner who helps them think ahead, protect their time, and operate at their best.

This role is best suited for career Executive Assistants who approach their work as a craft, operate with confidence and care, demonstrate exceptional attention to detail, and thrive in a flexible, remote work environment.

• Master complex calendars — true calendar tetris: multi-time-zone scheduling, competing priorities, and proactive planning to maximize executive focus
• Manage executive email inboxes with judgment, discretion, and polished communication
• Coordinate domestic and international travel — anticipating contingencies before they arise
• Build genuine rapport with clients — represent yourself and Boldly with warmth and confidence, earning trust quickly as a valued partner
• Anticipate needs and troubleshoot independently — you're the one who figures it out, not the one waiting for direction
• Prepare presentations, reports, and correspondence
• Manage expenses, projects, and administrative systems
• Navigate and leverage technology and AI tools responsibly and independently

The pay rate for this position is $27-$30 per hour with regular raises throughout your tenure. In addition to the hourly pay, total compensation includes benefits such as a 401(k) with employer match.

• 100% remote work, no nights or weekends
• Flexible schedule within regular business hours
• Medical, dental, vision, and life insurance
• 401(k) with employer match
• Paid time off and paid holidays
• Paid parental leave
• Ongoing mentorship and professional support from your Boldly Team Leader
• A people-first culture built on respect, transparency, and flexibility

You’ve spent years mastering your role as an EA. You communicate clearly and proactively, take ownership, and hold yourself to a high standard because details matter. You approach every interaction with kindness, carry confidence in your abilities, and build trust quickly — sustaining it over time.

At this point in your career, your #1 priority is to join a fully remote company that prioritizes flexibility in the workplace, and that promotes a culture of respect, kindness, and transparency.

• 7+ years of hands-on experience as an Executive Assistant or Senior Administrative Assistant providing true EA-level support (general administrative experience within another role does not meet the minimum qualifications for this position)
• Expert-level calendar management, including multi-time-zone scheduling and calendar strategy
• Skilled in coordinating travel and overseeing executive inboxes
• Proficient in Google Workspace and Microsoft 365, with the ability to adopt new technology and AI tools quickly
• Comfortable and professional on video calls (e.g., Zoom) when interacting with senior leaders and clients
• Clear, polished written and verbal communication that builds strong client relationships
• Proven ability to work independently, manage competing priorities, and stay organized without being prompted
• Location requirement: must reside in one of the 48 contiguous United States or in Alaska