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 $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

• It is not basic admin or routine tasks
• It is not a role you can combine with another full‑time job or side gigs
• It is not a role for those who struggle with or avoid technology
• It is not a stepping‑stone or training position; it is for career Executive Assistants already operating at a high level

We believe experienced professionals should not have to sacrifice flexibility to do meaningful,…