Boldly Premium Subscription Staffing

Who we are

Boldly is a premium subscription-staffing company offering long-term remote executive-assistant and senior-administrative support to Fortune 500 companies, non-profits, and high-level executives. Legal entity: Worldwide101 Inc., dba Boldly Premium Subscription Staffing. Founded in 2012 as a remote-first company — and 100% remote ever since. Offices at 295 Madison Ave., 12th Floor, New York, NY 10017 and Pury Hill Business Park, Towcester, Northants, NN12 7LS (UK).

How it works

Boldly hires senior, experienced executive assistants (and adjacent roles like project management, bookkeeping, multilingual support and marketing/social-media support) as W2 employees — not 1099 contractors. Team members typically support 1-3 clients on long-term engagements (often 2-3 years per client), with new matches based on skills and personality fit. Crucially, candidates meet with prospective clients to confirm mutual fit before engagement begins.

Pay & benefits

The full-time executive-assistant role is paid at $30/hour with regular tenure-based raises. Full-time employee benefits explicitly listed by Boldly include:

• W2 employment status (not 1099)
• Medical, dental, vision and life insurance with 100% of premiums paid by Boldly
• 401(k) with employer match
• Paid time off (vacation/sick) and paid holidays
• Paid parental leave
• Technology stipend
• Ongoing mentoring and support from a Boldly Team Leader

Schedule expectations

Boldly requires availability Monday-Friday during US business hours, with both morning and afternoon availability each working day, minimum 4 hours/day. Full-time = 32-40 hr/week; part-time = ≤31 hr/week.

Recognition

Boldly has been certified a Great Place to Work for 5 consecutive years, and has been named to Fortune Magazine's "50 Best Small Workplaces", Entrepreneur Magazine's "Entrepreneur 360 List", Color Magazine's Top Inclusive Workplace list, Military Friendly's Top 10 Military Spouse Friendly Employers, and FlexJobs Top 100 Companies. Accredited by Flexa as a truly flexible employer.

Diversity commitment

Boldly is a woman-owned business and is intimately familiar with the challenges women and minorities face in the workplace. The team includes parents, military spouses, caregivers, and others for whom remote/flexible work is not a perk but a necessity. Fostering a thriving company culture where everyone has a sense of belonging and enjoys coming to work is our #1 priority. Boldly is committed to maintaining a diverse, equitable and inclusive workplace for all.

Hiring process notes

Boldly considers LinkedIn to be the foundation of every applicant's professional online presence; all candidates that wish to apply must have an up-to-date LinkedIn profile (applications without a functional link directing to a LinkedIn profile are automatically declined). The application asks candidates to provide authentic, AI-free responses about why they want to work for Boldly and why they'd be a good fit. Boldly is committed to hiring military spouses and is named as part of Military Friendly's Top 10 Military Spouse Friendly Employers.