GUIDE REMOTE-FIRST

Remote Hiring Guide

Your next great hire is probably 3,000 miles away. Here's how to find them, interview them, and bring them onboard.

58% of workers want remote options
7x more applicants for remote jobs
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Why small teams have the advantage: Less bureaucracy, faster decisions. You can offer flexibility big companies can't. And you get access to global talent at competitive rates.

What this guide covers:

  • • Where to find remote candidates
  • • How to interview and assess remotely
  • • Legal considerations (it's complicated)
  • • Onboarding across time zones

Remote-First Job Boards

Tier 1: Remote-Specific Platforms

Platform Best For Cost
We Work Remotely Tech, design, marketing $299/post
Remote OK All roles, good reach $299/post
FlexJobs Verified listings, senior roles $299-399/post
RemoteWoman Diversity hiring $99/post
Working Nomads Digital nomads Free tier available

Tier 2: General Platforms with Remote Filters

LinkedIn - Best for senior roles
Indeed - Volume, lower quality
AngelList - Startup talent
Glassdoor - Company reviews matter

Tier 3: Niche Communities

  • Tech: Hacker News "Who's Hiring", Stack Overflow
  • Design: Dribbble, Behance jobs
  • Marketing: GrowthHackers, Superpath
  • International: Landing.jobs (EU), Turing (global)

Pro tip: Post on 3-5 boards minimum. Different platforms attract different candidate profiles.

Post Once. Reach Remote Candidates Everywhere.

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What to Look for in Remote Workers

Skills that matter MORE for remote work:

1. Written Communication

Remote work is 80% written. Look for clear emails, well-structured responses.

Test: Give a written exercise before interviews

2. Self-Direction

No one's watching over their shoulder. Look for examples of autonomous work, side projects.

Ask: "Tell me about a time you completed a project with minimal oversight"

3. Time Management

Results matter, not hours online. Look for evidence of meeting deadlines.

Red flag: "I work best with lots of structure and check-ins"

4. Tech Comfort

Video calls, async tools, documentation.

Baseline: Can they show up to a video interview without issues?

Remote-Specific Screening Questions

  • • Have you worked remotely before? What did you love/hate?
  • • How do you structure your workday when no one's watching?
  • • How do you handle loneliness or isolation?
  • • What time zone are you in, and what hours do you prefer?
  • • What does your home office setup look like?

The Remote Interview Process

Video Interview Best Practices

For You:

  • • Test your tech before every interview
  • • Good lighting, clean background (or blur)
  • • Look at camera, not screen (eye contact)
  • • Have questions on second monitor

For Candidates:

  • • Send invite with video link + backup phone
  • • Include: What to expect, who they'll meet
  • • Technical issues happen—have a plan B

Remote Interview Structure

Round 1: Async Video (Optional but powerful)

Send 3-5 questions via Loom. Candidates record responses on their own time. Saves hours of scheduling.

Round 2: Live Video Screen (30 min)

Culture and communication assessment. Role fit and expectations. Decide: Move forward or not.

Round 3: Deep Dive Interview (60-90 min)

Technical or role-specific assessment. Behavioral questions. Team member involvement.

Round 4: Work Sample or Trial

Paid trial project (1-5 hours). Real work they'd actually do. Always pay for this (typically $50-500).

All Your Remote Interviews, Tracked in One Place

Schedule, score, and compare candidates—no spreadsheets required.

See the Pipeline →

The Complicated Part: Legal Considerations

Domestic Remote Hiring (Same Country)

In the US, different states have different requirements:

States to Watch:

  • California: Strictest employment laws, expense reimbursement required
  • New York: Similar complexity, NYC has additional rules
  • Colorado: Must include salary in job postings

International Remote Hiring

Option 1: Contractor relationship

Simpler but risky if misclassified

Option 2: Employer of Record (EOR)

Third party employs them legally (Deel, Remote.com, Oyster). Cost: $400-700/month per employee

Option 3: Open local entity

Only if you're hiring many in one country

Contractor vs. Employee (The Big Risk)

Misclassification can result in back taxes + penalties, benefits owed retroactively, and legal action.

General rule: If you control when, where, and how they work, they're an employee, not a contractor.

Setting Up Remote Hires for Success

Pre-Day-One Checklist

Week 1 Structure

Day Focus Activities
Day 1 Welcome Team intro, culture overview, admin setup
Day 2 Context Product deep-dive, company history, goals
Day 3 Role Specific training, shadow sessions
Day 4 Practice First small tasks with guidance
Day 5 Connect 1:1s with key team members

Remote-Specific Onboarding Tips

1. Over-communicate context

They can't absorb culture by osmosis. Document everything. Explain the "why" behind processes.

2. Schedule social time

Virtual coffee chats. Team calls that aren't all work. In-person meetups if possible (quarterly).

3. Daily check-ins (week 1)

15 minutes, same time daily. "What are you working on? What's confusing?" Reduce to weekly after first month.

4. Set clear expectations

Working hours/availability. Communication preferences. Response time norms. Meeting cadence.

Ready to Hire Your First Remote Employee?

Remote hiring isn't harder—it's different. Start with one remote hire. Learn the process. Scale from there.

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