Executive Assistant

Role overview

Boldly is seeking an experienced career executive assistant to provide long-term support to senior leaders in the tech sector. This is a fully remote position with a flexible schedule during business hours and no evening or weekend shifts. The role is with Boldly as an employee supporting senior executives at established Fortune 500 companies.

Core duties

• Handle complex executive calendars with a strategic approach.
• Coordinate meetings, conferences, and travel plans.
• Book flights, hotels, and related travel arrangements.
• Save executive time by reviewing and routing messages, preparing correspondence and documents, gathering and analyzing information, and making calls on the executive’s behalf.
• Oversee multiple executive email inboxes.
• Track and manage expenses.
• Support customers and suppliers as needed.
• Carry out additional executive administrative tasks when required.

Candidate profile

The ideal candidate brings at least 7 years of direct experience supporting one or more executives in an executive assistant or senior administrative assistant capacity. Experience must be hands-on and in a true executive support role; general administrative work performed as part of another position does not meet the requirement. The role suits someone who wants to work for a remote-first company that values flexibility, respect, kindness, and transparency.

You should be a dependable team player with strong communication skills, a positive attitude, and a genuine desire to help others succeed. You’ll need to combine technology with a personal touch, stay proactive and flexible, and maintain a high standard of accuracy and professionalism.

Requirements and skills

• Minimum 7 years of direct executive assistant or senior administrative assistant experience supporting one or more executives.
• Advanced proficiency with tools such as Google Workspace, Microsoft Office 365, Zoom, and similar productivity platforms.
• Comfort juggling multiple priorities and shifting tasks efficiently.
• Strong organization and time management abilities.
• Ability to pick up new software and systems quickly.
• Excellent interpersonal communication skills.
• Strong written communication.
• Ability to work independently and meet deadlines under pressure.
• Problem-solving mindset.

Benefits

• W2 employment status for full-time employees.
• Medical, dental, vision, and life insurance with 100% of premiums covered by Boldly.
• 401(k) plan with employer match.
• Paid time off, including vacation and sick leave.
• Paid holidays.
• Paid parental leave.
• Technology stipend.
• Ongoing mentoring and support from a Boldly Team Leader.

Compensation

The pay for this role is $30 per hour, with regular raises over time. Total compensation also includes benefits such as the 401(k) match.

Culture and company background

Boldly promotes a career model that supports personal responsibilities and life choices. Its team includes parents, military spouses, caregivers, and people with varied life circumstances who benefit from flexible remote work. The company is woman-owned and committed to diversity, equity, and inclusion. Founded in 2012, Boldly has operated as a remote-first company since the beginning and has built extensive expertise in leading remote teams.

The company has been recognized as a Great Place to Work for five consecutive years and has also been included in Fortune Magazine’s “50 Best Small Workplaces,” Entrepreneur Magazine’s Entrepreneur 360 list of “Best Entrepreneurial Companies in America,” and Color Magazine’s top Inclusive Workplaces. It has also been named among the Top 10 Military Spouse Friendly Employers by Military Friendly, listed by FlexJobs as a Top 100 Company to Watch, and accredited by Flexa as a truly flexible employer.

Additional information

Boldly hires highly skilled executive assistants for both full-time and part-time roles. This position is based in the United States and is 100% remote.