Hire Offshore Executive Assistants for Chicago Businesses

Calendar & meeting orchestration

• • Own your calendar end to end, resolve conflicts, and protect deep-work blocks
• • Coordinate meetings across time zones with investors, board members, and customers
• • Prep agendas, send pre-reads, and circulate action items after every call

Travel & logistics planning

• • Book flights, hotels, ground transport, and visas through Navan or Concur
• • Build detailed day-by-day itineraries with backup plans and local contacts
• • Handle last-minute rebooking when flights are cancelled or meetings move

Stakeholder communication & gatekeeping

• • Triage inbound email, filter noise, and draft replies in your voice
• • Screen meeting requests against your real priorities, not just availability
• • Handle sensitive communications with board members, investors, and the press

Research & briefing prep

• • Build one-page briefings on every external meeting attendee and their context
• • Research companies, markets, and counterparties before key conversations
• • Compile board decks, quarterly update docs, and investor pre-reads

Light project & expense management

• • Track small internal projects, deadlines, and follow-ups across the exec team
• • Reconcile expenses in Expensify and chase receipts without needing reminders
• • Coordinate gifts, offsites, and personal logistics when work and life overlap

How much does it cost to hire an offshore executive assistant?

A full-time dedicated offshore executive assistant starts at $1,500 per month with Remoteria, rising to $2,200 for EAs with 5+ years supporting founders or C-suite. US-based EAs cost $75,000–$110,000 per year fully loaded, so you typically save 65–75%. The rate covers recruitment, scenario-based judgment interviews, onboarding, and ongoing account management.

How is an EA different from a general virtual assistant?

An EA is a senior role with judgment authority. A VA executes tasks you hand off; an EA decides which meetings are worth your time, drafts replies in your voice without constant check-ins, and handles sensitive board and investor communications. EAs in our network have prior experience supporting founders, CEOs, or managing partners directly and are paid for their discretion, not just their task throughput.

How do you handle confidentiality and board-level information?

Every EA signs a board-level NDA and IP assignment before receiving any access. For highly sensitive work we scope access narrowly — a separate email alias, limited calendar permissions, and shared drives rather than full inbox access — and log every document view. Most of our EAs have already handled cap tables, term sheets, and compensation data for other founders before we introduce them to you.

Can my EA make decisions without constantly asking me?

Yes, within a written decision authority document you co-author in week one. Typical authorities include rescheduling meetings under a cost threshold, approving expenses under a set dollar amount, drafting responses to routine external requests, and declining low-value meetings on your behalf. Anything outside the boundary goes to a Slack DM with a recommended answer, so you usually just reply "yes."

What happens if my EA is sick or on leave?

You get backup coverage within 4 hours. Because every EA maintains a living operations doc in Notion with calendar rules, contact lists, active projects, and decision authorities, a backup EA from our bench can step in and run the basics the same day. For planned leave we introduce the backup two weeks ahead so the handoff is clean, and your free replacement guarantee runs through the first 30 days if the fit is wrong.

How does timezone work between Chicago and an offshore virtual assistant?

Your offshore hire typically overlaps your morning, from roughly 9am CT to 3pm CT. That covers the bulk of your inbox, vendor calls, and team stand-ups. Anything async — reports, research, data cleanup — runs overnight and is waiting when you get in.

Do you work with Chicago trading firms, logistics companies, and manufacturers?

Yes. Most Chicago clients are in trading and fintech in the Loop, logistics operators around O'Hare, industrial distributors in the suburbs, and SaaS startups in Fulton Market. We match roles to specific workflows like trade ops, dispatch support, and AP/AR for mid-market businesses.

How fast can a Chicago business get an offshore hire started?

Chicago owners tend to want tight timelines and clear deliverables, and we run on that pace. Book a 15-minute call, send us the role, and we shortlist 3 vetted candidates in 5 business days. Most Chicago clients interview on day 6 and onboard by day 10.

How does offshore hiring compare to Chicago's local talent market?

Chicago talent is cheaper than NYC or SF but the prop trading and consulting ecosystem keeps the operational floor higher than people expect. A mid-level analyst in the Loop closes at $75,000–$95,000 base, and trading support roles near LaSalle now routinely cross $110,000. Offshore hiring delivers a comparable analyst or operations skill profile in 5 business days at roughly 35 percent of loaded Chicago cost. The bigger value for Midwestern owners is retention — offshore hires do not get poached into Citadel or Jump Trading every 18 months the way local Loop talent does.

Do Chicago businesses have any special requirements for offshore hires?

Offshore contractors are not US tax residents, so Chicago businesses do not withhold federal or Illinois state income tax, do not pay Illinois unemployment insurance, and do not file W-2s for these workers. The standard form is a W-8BEN collected at engagement (not a W-9, which applies only to US persons) governed by an independent contractor agreement. Illinois workers' compensation requirements do not apply to non-US workers performing services entirely outside the state. Most Chicago clients route payments through us, so they never deal with international wires or Cook County payroll filings directly.