Hiring the right executive assistant (EA) can make or break a founder’s productivity. At Strivo, we know that you don’t just need help—you need someone who thinks like you, acts fast, and can anticipate what’s next. That’s why our vetting, hiring, and training process isn’t just detailed—it’s elite.

In this behind-the-scenes look, you’ll learn exactly how we identify top-tier talent, equip them to thrive in high-pressure startup settings, and turn them into strategic partners who help founders lead with clarity and focus.

Why We Don’t Hire Freelancers or Generalists

Let’s start with what we don’t do.

We don’t pull from gig platforms or slap together a list of virtual assistants with vague titles and shallow skills. And we definitely don’t believe in generalists who are “okay at everything.” Why?

Because founders don’t need okay—they need outstanding.

Strivo EAs are:

• Dedicated full-time professionals
  
• Trained specifically for startup and C-suite environments
  
• Vetted for executive-level communication, prioritization, and problem-solving
  

By focusing on elite specialists instead of jack-of-all-trades freelancers, we ensure our EAs are built for strategic delegation—not just task completion.

Our Multi-Step Vetting Process

Our vetting process is rigorous by design. We’re not just looking for someone who can book meetings or sort inboxes—we’re looking for proactive thinkers, master communicators, and steady partners who can handle chaos with a calm mindset.

Here’s how our vetting process works.

Application & Experience Screening

Every candidate starts with a comprehensive application that goes far beyond a basic resume.

We look for:

• Previous EA or Chief of Staff experience
  
• Exposure to fast-paced startup environments
  
• Strong written and verbal communication skills
  
• Career trajectory that signals commitment and growth
  

We specifically screen out candidates with only general VA experience or short-term freelance gigs.

Situational Testing & Simulation Tasks

Next, candidates are given real-world simulations that test how they would operate in typical (and atypical) startup scenarios.

They’re asked to:

• Prioritize a cluttered schedule filled with overlapping meetings
  
• Write a sensitive email on behalf of a founder
  
• Identify bottlenecks in a founder’s current workflow
  
• React to urgent reschedules or investor requests
  

These exercises allow us to assess how well candidates think on their feet, communicate under pressure, and problem-solve proactively.

Final CEO-Centric Interview

The last step is a final video interview that mimics the founder-EA dynamic.

Here, we evaluate:

• Executive presence and demeanor
  
• Communication clarity
  
• Ability to listen, distill, and act
  
• Cultural alignment with startups and high-growth teams
  

Only candidates who demonstrate thoughtfulness, empathy, initiative, and confidence make the final cut.

Intensive Training for Real Startup Environments

Once vetted, our new hires aren’t just thrown into the deep end. They enter our proprietary Strivo EA Training Program—a structured onboarding experience designed to simulate real-world startup challenges.

Our training covers:

• Calendar triage and optimization strategies
  
• Founder inbox systems and tools (Superhuman, Gmail, Slack, etc.)
  
• Asynchronous communication frameworks
  
• Executive reporting and team coordination
  
• Time-blocking for founder productivity
  
• Energy-based scheduling and prioritization
  
• Advanced documentation and SOP creation
  

We don’t teach assistants how to assist. We teach them how to become extensions of a founder’s brain.

Training is led by operations pros who’ve supported CEOs, YC founders, and venture-backed execs. The goal? To ensure every EA we place shows up like an experienced operator from Day 1.

Continuous Development and Feedback Loops

At Strivo, training doesn’t stop at onboarding.

We believe in continuous growth—and that means giving every EA regular access to:

• Monthly performance reviews
  
• Peer mentoring and cohort learning
  
• Founder feedback surveys
  
• Access to new tools, strategies, and time-saving hacks
  

We also use internal metrics to track every EA’s responsiveness, quality of work, and ability to adapt. If someone’s not meeting the bar, we either coach them up or replace them with someone who will exceed expectations.

Our ongoing development process ensures that Strivo EAs don’t just stay good—they get better every quarter.

What Makes a Strivo EA Different

What truly sets a Strivo EA apart? Let’s break it down:

1. Strategic Thinking:
They don’t wait for instructions. They see patterns, ask better questions, and help founders think bigger by freeing up mental space.

2. Tech Fluency:
Our EAs are fluent in the tools you already use—Google Workspace, Notion, Slack, Trello, Calendly, Zoom—and can onboard new platforms quickly.

3. Founder Empathy:
Every Strivo EA is trained to understand founder psychology: the highs, the pressure, the decision fatigue. That insight fuels better partnership and trust.

4. Clear, Confident Communication:
You won’t get vague messages or delays. You’ll get clear updates, proactive nudges, and communication that sounds like you wrote it yourself.

5. Results-Driven:
Our assistants are obsessed with outcomes, not just activity. They’ll spot inefficiencies, fix broken systems, and bring real ROI to your calendar and communication flow.

Founder Onboarding: Setting Up for Success from Day One

Hiring a world-class executive assistant is only half the battle. The other half? Making sure the founder is equipped to delegate, communicate, and collaborate with confidence.

At Strivo, we invest just as much in your onboarding as we do in your EA’s. Why? Because we’ve seen firsthand that even the best assistant can only succeed if the founder sets the right foundation.

Here’s what our founder onboarding includes:

Personalized Delegation Playbook

We help you map out exactly what to offload first—calendar management, inbox zero strategies, investor follow-ups, recurring meetings, and more. It’s not about dumping tasks. It’s about building a system.

Communication Preferences & Style Mapping

Hate Slack pings after 7 p.m.? Want updates every Friday instead of daily check-ins? We document your communication style and embed it into your EA’s onboarding plan, so you’re never overwhelmed or micromanaging.

Founder Time Audit

We do a quick audit of your current calendar and work week to spot inefficiencies, redundant meetings, or admin black holes where time is getting lost. This allows your EA to step in with confidence and make immediate impact.

Trust-First Onboarding Flow

You’ll never be left guessing what to do with your EA. We guide both of you through a structured 30-day plan that fosters trust, clarity, and aligned outcomes. No awkward starts. Just a clean runway for takeoff.

This founder-centric approach ensures that by the time your EA is up to speed, you’re just as ready to lead more strategically—and finally stop doing the $25/hour tasks that distract from your million-dollar decisions.

FAQs About Our Executive Assistants

How long does it take to match with a Strivo EA?
On average, it takes 5–10 business days after onboarding to match with your EA. We use detailed questionnaires and discovery calls to align your preferences with the right partner.

Can I replace my EA if things don’t work out?
Absolutely. If you feel like something’s off, we offer fast, no-fuss replacements—usually within a week.

Are Strivo EAs full-time or part-time?
Most of our EAs work full-time hours or close to it, depending on your business needs. We build long-term matches, not short-term gigs.

What kind of founders use Strivo?
Our clients include solo founders, startup CEOs, and leaders at venture-backed companies who want to spend more time thinking strategically and less time juggling admin chaos.

What does onboarding look like?
Once you’re matched, we provide onboarding support to guide you and your EA through expectation setting, tool access, workflows, and communication preferences.

Here’s What Makes Strivo’s Process Elite

We’re not in the business of selling hours—we’re in the business of creating high-impact partnerships between founders and executive assistants.

At Strivo, every EA is:

• Vetted for performance, precision, and professionalism
  
• Trained to handle chaos, scale, and startup ambiguity
  
• Monitored and coached to constantly improve
  

If you’re a founder stuck in a loop of inbox overload, endless reschedules, or reactive communication—it’s time to bring in a pro.

Built for Founders Who Can’t Afford to Waste Time

At the end of the day, Strivo isn’t just about hiring great executive assistants—it’s about helping founders stay focused.

Our behind-the-scenes process reflects our obsession with quality, speed, and fit. We don’t believe in shortcuts. We believe in long-term trust, high standards, and empowering leaders to do their best work—without burning out.

Because when your executive assistant is world-class, you get to be world-class too.

Let’s fix your calendar, clean your inbox, and reclaim your time. Book a discovery call today!