If you’re a teacher looking to move into EdTech, you’ve likely felt the frustration. You spend hours scrolling through massive job boards like LinkedIn or Indeed, sifting through thousands of irrelevant listings, feeling like you’re alone in the desert. The promise of a fulfilling new role starts to feel like a mirage you can’t even trick yourself into seeing.
What if there was a better way? What if someone who truly understands the journey could curate the best opportunities for you?
That’s exactly what former 7th-grade teacher Chelsea Averitt set out to do when she founded Skip, the go-to job board and resource hub for educators transitioning into remote roles. I recently sat down with Chelsea on the Always A Teacher podcast to discuss her journey and the hard-won lessons she’s learned while helping thousands of teachers find their next career.
The Problem That Sparked a Mission
Like many of the people she now serves, Chelsea started out in the classroom. She understood the passion, the challenges, and the unique skill set that educators possess. She also understood the overwhelming feeling of trying to navigate a career transition with little guidance.
The “aha” moment came when she realized just how broken the job search process was for educators.
“You can go on LinkedIn and search for ‘EdTech’ and get a million results that have nothing to do with what you’re looking for. I saw a clear need for a curated, centralized place where educators could find high-quality, remote jobs in EdTech and education-adjacent industries without all the noise.”
Chelsea didn’t just see a problem; she built the solution. Skip was born not from a business plan, but from a genuine desire to solve a pain point for her fellow educators. It’s a platform built on the idea that teachers deserve a clearer, more direct path to roles that value their experience.
The Hard Truth About Today’s Job Market
One of the most valuable things Chelsea shares with her community is a dose of reality. In today’s competitive landscape, the job search isn’t a quick sprint; it’s a marathon.
“I’m very honest with my audience. It’s probably going to take you three to six months, if not longer, to land a role. My best advice is to get your head right and be patient with the process.”
This transparency is refreshing in a world full of “get a job in 30 days” promises. Acknowledging the timeline allows transitioning teachers to set realistic expectations and focus on a deliberate, strategic search rather than burning out in a frantic scramble for the first available offer.
Your First Move: Look Inward, Not Outward
So, what’s the first step in this marathon? According to Chelsea, it isn’t polishing your resume or hitting “apply” on dozens of job postings. It’s taking a step back to conduct a thorough skills inventory.
“You have to get really clear on what you want before you start looking. So many people just start spraying and praying their resume everywhere. You need to inventory your skills first. What are you good at? What do you enjoy doing? What parts of your teaching role can translate into a new career?”
This foundational work is critical. It’s what allows you to move from a reactive job seeker to a proactive career strategist. When you understand your own value, you can target the right roles, tailor your applications, and articulate your worth with confidence.
For teachers who have spent their careers in a single role, this can be the most challenging—and most rewarding—part of the journey. You’re not just a “teacher”; you’re a project manager, a communications expert, a data analyst, and a conflict resolution specialist. Seeing yourself through that lens is the key to unlocking your potential in the EdTech space.
Ready to start your own transition? Begin by mapping out your journey with our EdTech Transition Checklist and listen to the full conversation with Chelsea Averitt here.