Hey there! 🌟
Two years ago, I was scrolling through remote job boards at 2 AM, feeling completely defeated. Every posting seemed to want 3-5 years of experience, advanced certifications, or skills I’d never heard of. I had enthusiasm, a decent work ethic, and absolutely zero remote work experience to show for it.
The worst part? I kept seeing the same advice everywhere: “Start freelancing to build your portfolio” or “Take on unpaid internships.” Easy to say when you need to pay rent next month, right?
Then I met Marcus. He is a customer success manager. Marcus landed his first remote role just eight months after being laid off from retail management. No tech background. No fancy degree. No connections in his industry. Just a strategic approach to positioning himself as someone companies wanted to take a chance on.
His story completely changed how I thought about breaking into remote work.
The Truth About “No Experience” in Remote Work
Here’s what Marcus taught me: When companies say they want “remote work experience,” they want candidates with varied remote backgrounds. They don’t want people who’ve only worked from home. They seek individuals who can work independently, communicate clearly, and deliver results without constant supervision.
The problem isn’t that you lack experience. The issue is that you don’t know how to translate your existing skills into remote work language. Every job you’ve ever had has given you transferable skills. Every volunteer role has provided skills as well. Even managing your own life has contributed skills that remote employers desperately need.
Companies hiring for entry-level remote positions care more about your potential and work style than your previous job titles. They just need proof that you can handle the unique challenges of working from home.
4 Strategies to Position Yourself as Remote-Ready
1. Audit Your Hidden Remote Skills
You already have more remote-relevant experience than you think. Look for these transferable skills in your background:
From any job:
- Project management — Organizing events, coordinating schedules, meeting deadlines
- Communication — Writing emails, presenting to groups, explaining complex topics
- Problem-solving — Troubleshooting issues, finding creative solutions, working under pressure
- Self-direction — Working independently, managing priorities, staying motivated
From life experience:
- Planning trips = project management and research skills
- Managing household budgets = financial analysis and attention to detail
- Coordinating family schedules = logistics and communication skills
- Learning new hobbies = adaptability and self-directed learning
Create a “skills inventory” document listing every capability you have, no matter how you gained it. This becomes your foundation for remote job applications.
2. Build Proof of Remote Work Capabilities
Since you can’t show remote work history, create evidence of remote work skills instead.
Quick wins to demonstrate remote readiness:
- Set up a professional workspace and take photos for your LinkedIn profile
- Complete online courses relevant to your target roles (many are free)
- Start a side project — blog, YouTube channel, small business, volunteer work
- Document your self-directed learning through certificates, portfolios, or case studies
- Practice video calls until you’re comfortable on camera
Communication portfolio building:
- Write LinkedIn posts about your learning journey
- Create brief video introductions showcasing your communication skills
- Offer to help local businesses with their social media or admin tasks
- Join online communities in your field and contribute valuable comments
3. Target Entry-Level Remote-Friendly Roles
Some roles are naturally easier to break into remotely. Focus your search on positions that:
High-demand, entry-level remote roles:
- Customer service representative — Most companies offer training
- Virtual assistant — Wide range of tasks, flexible skill requirements
- Content moderator — Social media platforms constantly hiring
- Data entry specialist — Detail-oriented work that’s easy to train
- Online tutor or teacher — If you have expertise in any subject
- Social media assistant — Great for digital natives
- Sales development representative — Many companies train from scratch
Industries actively hiring remote beginners:
- SaaS and tech companies (customer success, support)
- E-commerce businesses (operations, customer service)
- Digital marketing agencies (assistant roles, content creation)
- Online education platforms (support, community management)
- Remote-first startups (various entry-level positions)
4. Master the Remote Job Application Process
Apply differently than you would for traditional jobs. Remote employers evaluate candidates through a different lens.
Application strategy that works:
- Customize every application — Show you understand their specific remote work challenges
- Lead with your why — Explain your genuine interest in remote work beyond convenience
- Address the experience gap directly — “While I’m new to remote work, I’ve demonstrated [specific skill] through [concrete example]”
- Show initiative — Mention courses you’ve taken, tools you’ve learned, or preparations you’ve made
Stand-out application elements:
- Include a brief video introduction (30-60 seconds)
- Create a simple portfolio website showcasing your skills
- Write a thoughtful cover letter addressing their specific needs
- Follow up professionally but not aggressively
- Be prepared for skills-based assessments or trial projects
Your 30-Day Remote Job Search Plan
Week 1: Foundation Building
- Complete your skills inventory
- Set up your workspace and take professional photos
- Update LinkedIn profile with remote work focus
- Research 10 companies you’d love to work for
Week 2: Skill Development
- Enroll in 2-3 relevant online courses
- Start a small project to showcase your abilities
- Join industry-specific online communities
- Practice video calls with friends or family
Week 3: Application Preparation
- Create your portfolio website or document
- Write 3 different cover letter templates
- Prepare for common remote work interview questions
- Set up job alerts for entry-level remote positions
Week 4: Active Job Searching
- Apply to 10-15 positions per week
- Follow up on applications from previous weeks
- Network in online communities
- Refine your approach based on responses
Your Challenge This Week 🎯
Choose one entry-level remote role that interests you and spend one hour researching:
- What skills do job postings repeatedly mention?
- What tools or software do they commonly use?
- What challenges will someone in this role face?
- How can you start building relevant experience now?
Then take one concrete action toward building that experience. Sign up for a free course. Download the software to practice. Alternatively, reach out to someone doing that job for advice.
What type of remote work are you most interested in pursuing? Are there specific skills you’re worried about not having, or companies you dream of working for?
Hit me up in the comments and let me know. I love helping people navigate their path into remote work. Sometimes, an outside perspective can spot opportunities you might be missing.
Here’s to proving that passion and preparation can open doors that experience alone will not.
Talk soon, Tim
P.S. Remember: every expert was once a beginner. The remote workers you admire today all started somewhere, and many of them started exactly where you are now. Your fresh perspective and eagerness to learn might be exactly what the right company is looking for. 🚀
From Desk to Calm 