Boldly
Boldly is a bootstrapped, New York-based subscription staffing company (legal entity Worldwide101 Inc.) that supplies US-based W2 remote executive assistants with 10-15 years of experience to enterprise leaders, SMBs, solopreneurs, and non-profits via monthly subscription plans.
- Company typePrivate
- Founded2012
- HeadquartersNew York, United States
- Headcount101–250
- GTM typeB2B
- OfferingServices
What Boldly does
Boldly, operating through its legal entity Worldwide101 Inc. (founded 2012, headquartered in New York with a UK office in Towcester), is a premium subscription staffing company that provides remote executive assistants and adjacent administrative services to enterprise leaders, small businesses, solopreneurs, and non-profits. Its core offering is a month-to-month subscription for fractional or full-time EAs (10-15 years of experience minimum), delivered by US-based W2 employees — a structure that internalizes employment compliance and removes 1099 misclassification risk from the client. Boldly extends beyond the core EA product into nine service modules covering administration, project management, marketing and social media, customer service, bookkeeping, multilingual support, and personal support, and operates Schedule Assist, a proprietary scheduling tool integrated with Google and Microsoft calendars that the company claims is 55% faster than manual scheduling.
The business is run as a sales-led, consultative motion: prospective clients connect by phone, review candidate profiles, and meet the proposed EA before subscribing, with dedicated account managers and backup coverage supporting retention. Pricing is quote-based, billed monthly in advance, with annual increases in March and October, 2.9% card fees, and ACH as the standard method. The company is bootstrapped (no external funding disclosed), led by Founder/CEO Sandra Lewis alongside CEO Bill Harrison and COO Sharyanne McSwain, and has accumulated a multi-year record of workplace awards (Great Place to Work, Fortune Best Workplaces) and named enterprise customers including Ginkgo Bioworks, Permira, and 99Designs.
Revenue is generated entirely through recurring monthly subscriptions on multi-year client relationships, supported by light content marketing (blog, email newsletter) and earned media (Forbes, ABC News, FlexJobs). AI tooling (Otter.ai, Zapier) is used by EAs to enhance productivity rather than as a standalone product, and the firm has no disclosed patents, proprietary ML models, or external investment.
Boldly firmographics
Firmographics- Name
- Boldly
- Legal name
- Worldwide101 Inc.
- Website
- https://boldly.com
- Company type
- Private
- Founded year
- 2012
- Operating status
- Operating
- Headcount range
- 101–250 employees
- Short description
- Boldly is a bootstrapped, New York-based subscription staffing company (legal entity Worldwide101 Inc.) that supplies US-based W2 remote executive assistants with 10-15 years of experience to enterprise leaders, SMBs, solopreneurs, and non-profits via monthly subscription plans.
- Ownership category
- akta.pro rank
Boldly industry classification
Industry- Product category
- Executive Assistant Staffing
- NAICS
- Temporary Help Services (561320), Temporary Help Services (56132), Office Administrative Services (56111), Office Administrative Services (5611)
- SIC
- Services-Employment Agencies (7361), Services-Help Supply Services (7363), Services-Facilities Support Management Services (8744)
- akta.pro primary industry
- Clerical & Customer Support Temp Staffing (BPACACAC)
- akta.pro secondary industry
- VIP/White-Glove & Executive Support (BPAAABAL)
Keywords
Where Boldly is headquartered
LocationHeadquarters
- HQ city
- New York
- HQ country
- United States
- HQ region
- North America
Offices2 records
Markets served
Boldly business model
Business model- GTM type
- B2B
- Offering type
- Services
- Cost components
- Personnel, Operations, Marketing or Sales, Technology or R&D, Others
Revenue model
- Subscription Staffing - Monthly Plans: Monthly subscription plans for fractional or full-time remote executive assistants. Plans are billed in advance on a month-to-month basis with automatic renewal. Pricing varies by hours assigned, with part-time fractional plans as the advertised standard. Full-time staff (more than 130 hours/month) incur higher hourly billing rates.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Subscription | Monthly | Part-time/Fractional Plans |
Go-to-market motion2 records
Distribution channels2 records
Marketing channels3 records
Boldly product offering
Product offeringCore offering
Boldly provides premium remote executive assistants on a monthly subscription basis, staffed by US-based W2 employees with 10+ years of experience. Clients subscribe to fractional or full-time support and receive matched, vetted assistants across administration, project management, marketing, customer service, bookkeeping, multilingual, and personal support functions. The service is delivered through a consultative matching process and includes access to proprietary tools such as Schedule Assist.
Product overview
Boldly is a premium subscription staffing company offering a unified platform of remote executive assistant services. The core offering consists of Executive Assistants and Subscription Staffing, supported by a complementary scheduling tool called Schedule Assist. The service portfolio spans nine distinct service modules: Administration, Project Management, Marketing & Social Media, Customer Service, Bookkeeping, Multilingual Support, and Personal Support. All services are delivered by US-based W2 employees working remotely, with a focus on experienced professionals (10+ years) available on flexible fractional plans.
Differentiator
Problem solved
Functional benefit
Products and services
- Executive Assistants Premium remote executive assistants with 10+ years of experience providing high-level administrative, strategic, and personal support to leaders and executives at companies of all sizes.
- Subscription Staffing Monthly subscription-based staffing service providing fractional or full-time remote assistants as W2 employees, with flexible plans from part-time to full-time support and no long-term commitment.
- Administration Services Executive admin support including word processing, diary management, to-do list management, and CRM management for business operations.
- Project Management Services Virtual project management support including developing project plans, coordinating freelancers, managing timelines, researching vendors, and tracking budgets.
- Marketing & Social Media Services Marketing administration and social media support including marketing automation, email newsletters, blog writing, content scheduling, and social media analytics.
- Customer Service Virtual customer service support handling customer enquiries, order processing, inventory management, invoice processing, and refund handling.
- Bookkeeping Services Remote bookkeeping support including expense entry, invoicing, reconciliation, accounts payable/receivable, reporting, credit control, and payroll.
- Multilingual Support Services Subscription-based multilingual staffing supporting translation, call screening, travel arrangements, appointment setting, and customer service across multiple languages.
- Personal Support Services Personal assistant support for busy executives including appointment booking, travel planning, gift buying, research, expense claims, and event planning.
Quantifiable outcome
- 55% faster scheduling with Schedule Assist tool
- +2 more outcomes
Companies that use Boldly
Customer profileNamed customers8 records
Segments11 records
Ideal customer profiles2 records
Boldly technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Integration8 records
AI capability3 records
Feature3 records
Boldly partnerships and signals
Strategic signalScale indicators2 records
Recent moves6 records
Expansion highlights6 records
Boldly competitors and assessment
Company assessmentDirect peers
- BELAY: BELAY is a US-based virtual staffing company that provides remote executive assistants, bookkeepers, and marketers on a subscription basis—directly competing with Boldly's EA, bookkeeping, and project management service modules for the same SMB and enterprise leader customer base.
- Time Etc: Time Etc is a UK-founded virtual assistant service that matches executives with experienced remote assistants—closely overlapping Boldly's UK and US customer bases and the premium fractional EA subscription model.
- Prialto: Prialto provides managed virtual executive assistant and admin support teams, primarily for mid-market and enterprise clients—directly comparable to Boldly's subscription staffing model and multi-EA enterprise offering.
- MyOutDesk: MyOutDesk offers remote executive assistants and virtual support staff for real estate, mortgage, and other professional services—a direct competitor in the subscription remote EA staffing category with overlapping service modules.
- Wing Assistant: Wing Assistant provides dedicated remote executive assistants and virtual support on a subscription model—closely comparable to Boldly's premium remote EA offering, though with different staffing geographies.
- Equivity: Equivity offers subscription-based virtual paralegal, executive assistant, and bookkeeping services—directly competitive with Boldly's enterprise-focused admin and bookkeeping service modules.
Broad incumbents
- Upwork: Upwork is the largest freelance marketplace for virtual assistants and administrative contractors—a broad incumbent that overlaps with Boldly's SMB and solopreneur segment but lacks Boldly's compliant W2 staffing model and curated executive-level talent.
- Robert Half International: Robert Half is a global staffing and consulting firm with dedicated administrative and executive support placement—a broad incumbent whose traditional temp staffing and direct hire businesses overlap with Boldly's subscription EA model.
Regional players
- Wood Personnel Services: Wood Personnel Services provides office admin, clerical, and executive-support staffing across the Mid-South US—regionally comparable to Boldly's staffing model but without the premium remote-first subscription positioning.
Emerging players
- Fiverr: Fiverr operates as a marketplace for freelance executive assistants and virtual admin services—serving a similar SMB audience but without Boldly's W2 staffing, premium talent curation, and enterprise account management layers.
Market position
Strengths4 records
Weaknesses5 records
Competitive moat4 records
Key risks5 records
Key highlights7 records
Customer concentration
Boldly social profiles
Digital presenceBoldly compliance and trust
Trust signalCompliance15 records
Boldly financial estimates
Financial estimateRevenue estimate
Valuation estimate
Boldly leadership team
Management profileNumber of profiles
Profiles6 records
Boldly funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Boldly M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Boldly
What does Boldly do?
Boldly provides premium remote executive assistants on a monthly subscription basis, staffed by US-based W2 employees with 10+ years of experience. Clients subscribe to fractional or full-time support and receive matched, vetted assistants across administration, project management, marketing, customer service, bookkeeping, multilingual, and personal support functions. The service is delivered through a consultative matching process and includes access to proprietary tools such as Schedule Assist.
Is Boldly a public or private company?
Boldly is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was Boldly founded?
Boldly was founded in 2012. It employs 101 to 250 people.
Where is Boldly based?
Boldly is headquartered in New York, United States, in the North America region.
How does Boldly make money?
One revenue line is on record: subscription Staffing - Monthly Plans.
Who are Boldly's main competitors?
Direct peers on record are BELAY, Time Etc, Prialto, MyOutDesk, Wing Assistant and Equivity. Broad incumbents are Upwork and Robert Half International. Wood Personnel Services is listed as a regional player. Fiverr is listed as an emerging player.
Does Boldly have an API?
No public API is recorded for Boldly.
What industry is Boldly in?
Boldly's product category is Executive Assistant Staffing. Its primary akta.pro industry code is BPACACAC, Clerical & Customer Support Temp Staffing, with a secondary code of BPAAABAL, VIP/White-Glove & Executive Support. Its NAICS code is 561320 and its SIC code is 7361.