Building a Remote-First Company? Your First Hire Should Be an EA
You’ve decided to build a remote-first company. Smart move. You get access to global talent, reduced overhead costs, and the kind of operational flexibility that makes traditional office-bound competitors look like they’re moving in slow motion.
But here’s where most remote-first founders get the hiring sequence completely backwards. They start with developers, salespeople, or marketers… The roles that feel most directly connected to revenue.
Meanwhile, they’re drowning in the operational complexity that comes with coordinating a distributed team, and wondering why everything feels so much harder than it should.
Here’s the counterintuitive truth we’ve learned from hundreds of remote-first companies: your first hire shouldn’t be the person who builds your product or sells it. It should be the person who builds the operational foundation that lets everyone else do their best work.
That person is an Executive Assistant. But not the kind you might be imagining.
Why Remote-First Changes Everything About Early Hiring
Traditional startups can get away with operational chaos longer because proximity masks inefficiency. When everyone’s in the same room, you can shout across the office to clarify a miscommunication or grab someone for a quick decision. Informal coordination happens naturally.
Remote work doesn’t have that luxury. Every interaction requires intention. Every process needs documentation. Every communication gap that would be a minor annoyance in an office becomes a productivity black hole when your team is distributed across continents.
Most founders underestimate this operational overhead until they’re spending 40% of their time on coordination tasks that add zero business value. You’re not building a company… You’re managing the logistics of having a company.
The founders who scale remote-first successfully recognize this early and solve it strategically. They don’t just hire people to do the work; they hire someone to create the systems that make the work possible.
The Hidden Costs of Poor Remote Operations
Before we dive into solutions, let’s be honest about what’s really at stake when remote operations go sideways:
Decision latency becomes a growth killer.
Simple decisions that should take minutes stretch into days because the right people can’t connect efficiently. Your competitive advantage dies in coordination overhead.
Information silos fragment your team.
Important context lives in someone’s head or is buried in a Slack thread from two weeks ago. New hires spend weeks figuring out what everyone else already knows.
Meeting fatigue destroys productivity.
Without efficient async processes, everything becomes a meeting. Your team spends more time talking about work than doing it.
Time zone conflicts create bottlenecks.
Projects stall because key stakeholders are never online simultaneously. Your global talent advantage becomes a coordination nightmare.
Communication overhead scales exponentially.
Adding each new person creates exponentially more communication paths. A five-person team has 10 communication relationships; a ten-person team has 45.
These aren’t abstract problems, but they have real costs. We’ve seen companies burn through six months of runway just on operational inefficiency that could have been solved with the right early hire.
What Makes an EA Different in a Remote-First Context
When most people hear “Executive Assistant,” they picture someone answering phones and scheduling meetings. But in a remote-first company, an EA becomes something closer to a Director of Operations who happens to start by supporting the founder.
Here’s what that actually looks like:
They become your distributed team’s nervous system.
While you focus on product and market, they ensure information flows efficiently between team members who never see each other face-to-face.
They turn your communication chaos into scalable systems.
Instead of important updates living in random Slack threads, they create documentation standards and communication rhythms that work across time zones.
They protect your decision-making bandwidth.
Remote work generates more decisions per day than office work… where to document things, how to communicate updates, when to schedule across time zones. A great EA handles the operational decisions so you can focus on strategic ones.
They become your company’s memory system.
In remote teams, institutional knowledge can’t live in hallway conversations. Your EA documents processes, captures decisions, and ensures nothing critical gets lost when people aren’t physically present.
The First 90 Days: Building Remote Operations That Scale
Week 1-2: Infrastructure and Systems Setup
Your EA immediately tackles the operational foundation that most founders spend months cobbling together:
- Sets up proper communication channels with clear purposes (not just “general” Slack channels where everything gets lost)
- Implements basic project management systems that work across time zones
- Creates documentation templates and standards
- Establishes file organization and access protocols
You’re already spending less time on “where did we put that document” and more time on actual business decisions.
Week 3-6: Communication Rhythms and Process Documentation
This is where the magic happens. Your EA creates the operational rhythms that make remote work feel coordinated instead of chaotic:
- Implements async update systems so decisions don’t wait for meetings
- Documents your decision-making criteria so they can handle routine calls
- Creates onboarding templates for future hires
- Establishes regular communication cadences that keep everyone aligned
By week six, your company feels organized in a way that would have taken you months to achieve alone.
Week 7-12: Scaling Preparation and Advanced Operations
Now your EA is thinking ahead to the challenges you’ll face as you grow:
- Creates hiring workflows and interview coordination systems
- Implements customer communication standards and templates
- Sets up vendor management and procurement processes
- Develops crisis communication protocols
Three months in, you have operational systems that most companies don’t develop until they have 20+ employees.
Is This You? (Signs You Need EA-First Hiring)
Not sure if this approach makes sense for your situation? Here are some indicators that EA-first hiring could dramatically accelerate your growth:
You’re spending more time coordinating work than doing work.
If you’re constantly scheduling meetings, chasing down information, or explaining the same context to different people, operational overhead is killing your productivity.
Your team asks the same questions repeatedly.
This usually indicates poor information systems rather than poor people. The right EA creates documentation and communication flows that eliminate repetitive questions.
Simple projects take forever due to coordination complexity.
When basic tasks require extensive back-and-forth across time zones, you need better async systems and communication protocols.
You’re hesitant to hire because onboarding feels overwhelming.
If bringing on new team members feels like more work than help, you need systematic onboarding processes that scale.
You work odd hours to accommodate global team coordination.
While some time zone overlap is inevitable, excessive coordination burden usually indicates inefficient systems rather than a necessary sacrifice.
The Compound Benefits of Getting This Right Early
Hiring an EA first solves immediate operational pain and creates compound advantages that accelerate everything else:
Future hires integrate faster.
Instead of spending weeks figuring out “how we do things here,” new team members have clear documentation and onboarding systems from day one.
Decision velocity increases exponentially.
With proper information systems and delegation frameworks, decisions happen in hours instead of days.
Communication overhead decreases as team size increases.
Most remote teams see communication complexity explode with growth. Proper systems actually make larger teams more efficient than smaller ones.
Company knowledge becomes institutional rather than individual.
When key information lives in documented systems rather than people’s heads, you’re less vulnerable to team changes and can scale more confidently.
Your operational systems become a competitive advantage.
While competitors struggle with remote coordination chaos, your team executes with the efficiency of a much larger, more mature organization.
What to Look for in a Remote-First EA
Not every EA can handle the operational complexity of building remote-first systems. Here’s what separates the right candidates from the rest:
Systems thinking over task completion.
Look for candidates who instinctively ask, “How can we make this better next time?” rather than just completing individual requests.
Experience with distributed teams.
Remote work requires different skills from office support. Prioritize candidates who understand async communication, digital collaboration tools, and time zone coordination.
Process documentation skills.
In remote teams, if it’s not documented, it doesn’t exist. Your EA needs to be naturally inclined toward creating clear, usable documentation.
Technology fluency.
Remote-first operations run on digital tools. Your EA should be comfortable learning new platforms and optimizing digital workflows.
Cultural bridge-building abilities.
Distributed teams need intentional culture creation. Look for candidates who can facilitate team connection across distance and difference.
Proactive communication style.
Remote work requires over-communication and anticipation. Your EA should default to sharing more context rather than less.
Common Mistakes to Avoid
We’ve seen hundreds of remote-first companies navigate this decision. Here are the most expensive mistakes to avoid:
Hiring for traditional EA skills instead of remote operational skills.
Calendar management and email organization are table stakes. You need someone who can build distributed team systems.
Treating your EA like a traditional assistant instead of an operational partner.
Give them authority to make decisions and implement systems. If you’re micromanaging your EA, you’re missing the point.
Underinvesting in their understanding of your business.
Your EA needs to understand your strategy and priorities to make good operational decisions. Share context generously.
Focusing on cost instead of capability.
The cheapest EA is rarely the most effective for building operational systems. Invest in a capability that can scale with your ambitions.
Build Your Remote-First Company, i.e, Operational Foundation
Here’s a practical framework for what your EA should tackle in their first 90 days:
1. Communication Infrastructure
- Establish clear channel purposes and usage guidelines
- Create async update rhythms that work across time zones
- Implement documentation standards and templates
- Set up information archiving and retrieval systems
2. Decision-Making Frameworks
- Document your decision criteria for common scenarios
- Create escalation paths for different types of decisions
- Establish approval workflows that don’t create bottlenecks
- Build delegation guidelines that increase team autonomy
3. Team Coordination Systems
- Design onboarding processes that work for remote hires
- Create project management workflows that provide visibility without micromanagement
- Implement regular team connection and culture-building practices
- Develop crisis communication and rapid response protocols
4. Scaling Preparation
- Build hiring and interview coordination systems
- Create vendor management and procurement processes
- Establish customer communication standards and templates
- Document company knowledge and institutional memory
The Long-Term Strategic Advantage
Companies that nail remote operations early don’t just survive, but develop competitive advantages that compound over time. When your operational systems are excellent, several things happen:
You can hire the best talent globally instead of locally.
While competitors limit themselves to geographic talent pools, you can recruit from anywhere because your systems make integration seamless.
You can scale faster with higher quality.
Adding new team members accelerates progress instead of creating coordination overhead.
You become more resilient and adaptable.
When your systems work remotely, you can handle any disruption. That goes for economic downturns, global events, or rapid scaling opportunities.
Your team becomes your competitive moat.
While competitors struggle with remote coordination, your team executes with efficiency and clarity that’s hard to replicate.
The founders who recognize this early and invest in operational excellence from day one often find themselves competing against much larger companies with better efficiency and speed.
The Bottom Line
Building a remote-first company isn’t just about hiring people who work from home. It’s about creating operational systems that turn distributed work from a challenge into an advantage.
Most founders approach this backwards. They hire for immediate revenue generation and then struggle with the operational complexity of coordinating distributed work. By the time they realize they need better systems, they’re already behind and playing catch-up.
The smart play is to hire your operational foundation first. Get an EA who understands remote-first operations and can build the systems that make everything else possible. Then add revenue-generating roles to a foundation that’s designed for distributed success.
Your first hire sets the operational DNA for everything that follows. Make it count.
The question isn’t whether you can afford to hire an EA first. It’s whether you can afford to build on a weak operational foundation while your remote-first competitors are building on a strong one.
Ready to Build Your Remote-First Foundation?
At Anywhere Talent, we specialize in matching remote-first founders with world-class executive assistants who understand the unique operational challenges of distributed teams. Through our rigorous vetting process, we find EAs who can build the systems and processes that turn remote work from a coordination challenge into a competitive advantage.
Let’s build your remote-first operational foundation from day one.
