Squared Away
Squared Away is a US-based, bootstrapped professional services firm that provides dedicated executive and personal assistant support to founders, executives, startups, and VC firms, delivered remotely by a curated workforce of military spouses on tiered monthly subscriptions.
- Company typePrivate
- Founded2019
- HeadquartersKailua, United States
- Headcount101–250
- GTM typeB2B
- OfferingServices
What Squared Away does
Squared Away is a US-based, fully remote professional services company that provides dedicated executive and personal assistant support to founders, executives, startups, and venture capital firms, staffed by a workforce of military spouses. Founded in 2019 by CEO Michelle Penczak — herself a military spouse frustrated by the employment disruptions of frequent relocations — the company addresses a dual market need: portable, flexible careers for the military spouse community and reliable, US-based administrative talent for time-constrained business leaders. The core product matches each client with a dedicated military spouse assistant drawn from a pool of 1,000+ vetted members, with the broader team functioning as a shared knowledge layer for backup coverage and specialized expertise.
The service is organized into six functional sub-products (Scheduling and Travel Planning, Marketing and Social Media Management, Startup & VC Support, Time Optimization, Finance Optimization, and General Admin) and is delivered on a subscription basis across four tiers — Starter (15 hours/month at $600–$900), Team (25 hours at $1,000–$1,500), Executive (50 hours at $2,000–$3,000), and Premier (75 hours at $3,000–$4,500) — with pricing modulated by assistant tenure. The technology layer combines the human delivery model with third-party AI tools used for research, scheduling, document management, and communications; integrations include Canva, Planoly, QuickBooks, Gusto, and HubSpot. Ancillary revenue-adjacent assets include the Squared Away Community platform, The Delegation Dispatch newsletter (24k+ subscribers), and the Beyond Orders podcast. The company is privately held, bootstrapped, and headquartered in North Carolina with no disclosed external institutional funding.
Squared Away firmographics
Firmographics- Name
- Squared Away
- Legal name
- Squared Away
- Website
- https://gosquaredaway.com
- Company type
- Private
- Founded year
- 2019
- Operating status
- Operating
- Headcount range
- 101–250 employees
- Short description
- Squared Away is a US-based, bootstrapped professional services firm that provides dedicated executive and personal assistant support to founders, executives, startups, and VC firms, delivered remotely by a curated workforce of military spouses on tiered monthly subscriptions.
- Ownership category
- akta.pro rank
Squared Away industry classification
Industry- Product category
- Virtual Assistant Services
- NAICS
- Office Administrative Services (56111)
- SIC
- Services-Help Supply Services (7363)
- akta.pro primary industry
- Workforce Time, Attendance & Scheduling Administration (BPAAAIAI)
- akta.pro secondary industry
- Errand Running & Task Assistance (HSACAIAB)
Keywords
Where Squared Away is headquartered
LocationHeadquarters
- HQ city
- Kailua
- HQ country
- United States
- HQ region
- North America
Offices1 record
Markets served
Squared Away business model
Business model- GTM type
- B2B
- Offering type
- Services
- Cost components
- Personnel, Operations, Technology or R&D, Marketing or Sales, Others
Revenue model
- Subscription-based Assistant Services: Monthly subscription model with tiered pricing based on hours of service per month. Packages range from 15 hours to 75 hours monthly, with pricing varying by assistant tier (experience level). Billing is monthly with automatic renewal.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Subscription | Monthly | Starter: 15 hours/month with Tier 1 assistant |
| Subscription | Monthly | Team: 25 hours/month with Tier 1 assistant |
| Subscription | Monthly | Executive: 50 hours/month with Tier 1 assistant |
| Subscription | Monthly | Premier: 75 hours/month with Tier 1 assistant |
Go-to-market motion3 records
Distribution channels3 records
Marketing channels6 records
Squared Away product offering
Product offeringCore offering
Squared Away provides subscription-based executive and personal assistant services staffed by US-based military spouses. Clients are matched with dedicated assistants who provide scheduling, travel planning, marketing, social media management, inbox management, bookkeeping, and general administrative support on monthly plans ranging from 15 to 75 hours. The service model is team-based, with every client drawing on the broader Squared Away network for backup coverage, and is augmented by AI tools for research, scheduling, document management, and communication.
Product overview
Squared Away is a professional services company providing AI-augmented personal assistant support staffed by US-based military spouses. The core offering is the Military Spouse Assistant Services, a team-based model where clients are matched with dedicated assistants who draw on shared community knowledge and AI tools. The service is organized into distinct functional sub-products: Scheduling and Travel Planning, Marketing and Social Media Management, Startup & VC Support, Time Optimization (inbox management and CRM), Finance Optimization (bookkeeping via QuickBooks and Gusto), and General Admin. The company also offers a Leadership Community for client networking and growth, a newsletter (The Delegation Dispatch), and a podcast (Beyond Orders). Pricing is structured across four tiered hourly plans (Starter, Team, Executive, Premier) ranging from 15 to 75 hours per month, with three experience-based assistant tiers affecting hourly rates. AI is positioned as a force multiplier for the human assistants rather than a standalone product.
Differentiator
Problem solved
Functional benefit
Products and services
- Military Spouse Assistant Services
Quantifiable outcome
- 15-40 hours saved monthly per client
- +4 more outcomes
Companies that use Squared Away
Customer profileNamed customers7 records
Segments4 records
Ideal customer profiles3 records
Squared Away technology and API
TechnologyTechnology focussed No
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
Integration5 records
AI capability3 records
Feature5 records
Squared Away partnerships and signals
Strategic signalScale indicators12 records
Recent moves6 records
Expansion highlights5 records
Squared Away competitors and assessment
Company assessmentDirect peers
- BELAY: BELAY is one of the largest US-based virtual assistant and remote staffing companies serving executives and small businesses. It is the most direct competitor to Squared Away, offering similar subscription-based executive, marketing, and bookkeeping assistant services.
- Prialto: Prialto provides managed virtual assistant services for executives and small teams, with dedicated assistants and team-based support. Its subscription model and emphasis on integrated team coverage closely mirrors Squared Away's approach.
- Time Etc: Time Etc is a UK/US virtual assistant services company offering subscription-based executive and business support. It targets the same executive and founder customer base with a comparable tiered service model.
- Wing Assistant: Wing Assistant provides dedicated virtual assistants for startups, executives, and small businesses globally. Its subscription-based dedicated-assistant model and target customer segments overlap directly with Squared Away.
- MyOutDesk: MyOutDesk provides virtual assistant staffing for real estate, executives, and small businesses. It offers a similar subscription-based model with dedicated assistants sourced from a vetted talent pool.
- ClearDesk: ClearDesk offers dedicated offshore virtual assistants for e-commerce, marketing, and administrative tasks for SMBs and executives. It competes in the same dedicated-assistant subscription segment as Squared Away.
- Double: Double (formerly Delegate) provides executive assistants specifically to founders and tech executives, often via staffing from the Philippines. Its subscription model and tech/startup customer base overlap with Squared Away's executive and VC segments.
- Magic: Magic provides on-demand virtual assistants for executives, founders, and busy professionals via a subscription model. It overlaps with Squared Away's personal/executive assistance offering and target persona.
Broad incumbents
- Upwork: Upwork is the largest freelance marketplace, hosting thousands of virtual assistants and executive assistants. While it offers a broader service mix and self-serve model, it competes for the same customer dollars and serves as a substitute for Squared Away's bundled offering.
- Fiverr: Fiverr is a global freelance marketplace offering virtual assistant, admin, and executive support services. As a broad incumbent, it competes on price and flexibility against Squared Away's dedicated, subscription-based assistant model.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat4 records
Key risks7 records
Key highlights7 records
Customer concentration
Squared Away social profiles
Digital presenceSquared Away financial estimates
Financial estimateRevenue estimate
Valuation estimate
Squared Away leadership team
Management profileNumber of profiles
Profiles7 records
Squared Away funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Squared Away 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 Squared Away
What does Squared Away do?
Squared Away provides subscription-based executive and personal assistant services staffed by US-based military spouses. Clients are matched with dedicated assistants who provide scheduling, travel planning, marketing, social media management, inbox management, bookkeeping, and general administrative support on monthly plans ranging from 15 to 75 hours. The service model is team-based, with every client drawing on the broader Squared Away network for backup coverage, and is augmented by AI tools for research, scheduling, document management, and communication.
Is Squared Away a public or private company?
Squared Away is a private company. It is classified as founder individual operated bootstrapped and is currently operating.
When was Squared Away founded?
Squared Away was founded in 2019. It employs 101 to 250 people.
Where is Squared Away based?
Squared Away is headquartered in Kailua, United States, in the North America region.
How does Squared Away make money?
One revenue line is on record: subscription-based Assistant Services.
Who are Squared Away's main competitors?
Direct peers on record are BELAY, Prialto, Time Etc, Wing Assistant, MyOutDesk, ClearDesk, Double and Magic. Broad incumbents are Upwork and Fiverr.
Does Squared Away have an API?
No public API is recorded for Squared Away.
What industry is Squared Away in?
Squared Away's product category is Virtual Assistant Services. Its primary akta.pro industry code is BPAAAIAI, Workforce Time, Attendance & Scheduling Administration, with a secondary code of HSACAIAB, Errand Running & Task Assistance. Its NAICS code is 56111 and its SIC code is 7363.