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Your Experience Looks Impressive But Irrelevant
Why 10 years of experience isn't helping you get remote jobs
INSIDE THIS ISSUE:
This week's hot & vetted remote job picks
Why your impressive background isn't getting interviews
The translation problem nobody's fixing
How to make unrelated experience actually matter
Hi Freedom Seeker,
Hope you're getting some rest this week with Christmas coming up. Quick one today because I know you're busy.
Before you disappear for the holidays, I want to address something that's probably been frustrating you.
You have solid experience. Years of it. You've accomplished things. Built stuff. Managed teams. Delivered results.
But you're applying to remote jobs and hearing nothing back.
Here's what's happening: Your experience looks great. It's just not relevant to what they're looking for.
You spent 8 years in retail management. They want customer success experience.
You have a finance background. They need operations coordination.
You were a teacher. They're hiring for project management.
Your experience is impressive. It's just presented in a way that makes hiring managers think "wrong background" and move on.
The problem isn't your experience. It's that you're showing them what you did instead of what you can do.
🚀 Weekly Vetted Remote Job Picks
1️⃣ Company: HubSpot
🔷 Role: Senior Design Manager - Reporting
🔷 Location: US
🔷 Type: Full-time, fully remote
🔷 Perks: Remote-first, equity
🔷 Salary: $230,218—$368,396 USD per year
➡️ Apply Here
2️⃣ Company: Milked Media
🔷 Role: Paid Social + Email Graphic Designer
🔷 Location: North America
🔷 Type: Part-time, contract, fully remote
🔷 Perks: Flexible hours, asynchronous work
🔷 Salary: $32 per hour
➡️ Apply Here
3️⃣ Company: Canonical
🔷 Role: Customer Success - Team Manager
🔷 Location: Anywhere
🔷 Type: Full-time, fully remote
🔷 Perks: Remote-first, competitive benefits
🔷 Salary: Competitive
➡️ Apply Here
WHY IMPRESSIVE EXPERIENCE DOESN'T GET YOU HIRED
YOU'RE LISTING WHAT YOU DID, NOT WHAT YOU CAN DO
"Managed store operations with 15 employees" Cool. But what does that tell a remote company hiring for customer success?
Nothing. They see retail and think "not relevant."
But if you said: "Led team of 15 to resolve customer issues quickly, maintaining 92% satisfaction scores through clear communication and problem-solving" - now they see customer success skills.
Same experience. Completely different relevance.
YOU'RE USING THE WRONG LANGUAGE
Every industry has its own vocabulary. If you're switching from one field to another, you need to learn the new language.
Teachers call it "classroom management." Remote companies call it "project coordination."
Finance people say "reconciled accounts." Operations roles say "managed process accuracy."
Retail managers "handled escalations." Customer success "resolved critical client issues."
It's the same work. Different words. And the words matter.
YOU'RE NOT CONNECTING THE DOTS
Hiring managers are busy. They're not going to look at your retail experience and figure out how it applies to remote customer success.
You have to connect the dots for them.
"Okay, you managed a retail team. So what?" "I coordinated schedules, trained new hires remotely during COVID, and used our system to track performance metrics across locations."
Now they get it.
HOW TO MAKE YOUR EXPERIENCE RELEVANT
STOP LEADING WITH YOUR INDUSTRY
Don't say: "Retail Manager with 8 years experience"
Say: "Customer-focused leader with 8 years managing teams and resolving escalations"
The first one boxes you in. The second one shows transferable value.
TRANSLATE EVERY ACHIEVEMENT
Take what you accomplished and rewrite it in language that matches the job you want.
Teaching → Project Management: "Managed classroom of 30 students" becomes "Coordinated projects for 30+ stakeholders with competing priorities"
Finance → Operations: "Processed monthly reconciliations" becomes "Managed workflow accuracy and deadline adherence for critical operations"
Retail → Customer Success: "Resolved customer complaints" becomes "De-escalated client issues through proactive communication and solution-focused approach"
SHOW REMOTE-READY SKILLS FROM ANY BACKGROUND
Every job has elements that prove you can work remotely:
Did you work independently? That's self-direction.
Did you communicate via email? That's async communication.
Did you use any software? That's tech proficiency.
Did you coordinate with people in other locations? That's distributed teamwork.
Pull these out and highlight them. They're relevant to every remote job.
THE REAL PROBLEM
Your 10 years of experience should be an advantage. Instead, it's making you look like you're from a different world.
That's a positioning problem, not an experience problem.
The people who get hired aren't always the ones with the most relevant backgrounds. They're the ones who know how to position what they have in a way that makes sense for what companies need.
TIRED OF YOUR EXPERIENCE WORKING AGAINST YOU?
This is exactly what we fix in the 1:1 Job Search Partnership.
We take your actual experience and reposition it so remote companies see you as the solution, not a risk. We translate your background into language they understand and frame your achievements so they actually matter for remote roles.
Here's what we do:
✅ Audit your current positioning and find what's not working
✅ Translate your experience into remote-relevant language
✅ Rebuild your resume to show transferable value
✅ Position you strategically for the roles you actually want
✅ Weekly support to keep you on track
Most people start getting interviews within 2-3 weeks once their experience is positioned correctly.
Your background isn't the problem. How you're presenting it is.
Ready to stop getting ignored? Reply with "REPOSITION ME" and let's make your experience actually work for you.
Until next week,
Sami
Interested in getting your product/ remote job offering in front of highly engaged remote workers?