As the one-woman mastermind behind the beloved Skip’s Job Board, Chelsea Maude Avirett knows a thing or two about the education job market.

If you’ve been reading for a while, you’ve heard me rave about Skip’s, which curates all-remote education-related job postings that start at $60k per year. I’m constantly recommending it as a great starting place for transitioning teachers to get a sense of the ed-adjacent job market, the roles companies are hiring for, and the skills they’re seeking.

Chelsea has been running Skip’s since 2021 and now tracks over 500 companies that hire teachers across three categories: education, EdTech, and relevant skills. Let’s just say that this makes her uniquely positioned to give important insights about this job market. I was excited to catch up with Chelsea and pick her brain about this moment in the industry.

Why March Is Hiring Season For Education-Related Jobs

There tend to be a base number of jobs available year-round, including jobs for educators. But in March, Chelsea typically sees a bump in EdTech and ed-adjacent job postings.

“Companies know that a lot of teachers don’t want to break their contract,” she says. Given that the hiring process typically takes several months, a March job posting gives teachers time to apply and interview before they need to sign the next school year’s contract.

“So March is big,” Chelsea says. “I'll see jobs starting as early as December that say, ‘We want teachers.’ They’re really trying to get the people who are looking early, and they want to get the first pick of the crop, so to speak.”

During the pandemic, a lot of EdTech and curriculum companies were worried about stealing staff from schools. “If you are trying to sell to a school, you don't want to be seen as the person who's encouraging teachers to break contracts.”

Chelsea has seen less of this worry post-pandemic, “but there is that concern: ‘Are we going to get a bad reputation, and is that bad reputation going to make it hard for us to sell?’”

This year is different. Chelsea is posting the same overall number of jobs on Skip’s as in previous years—with the caveat that she’s added more companies to her database. “So we are seeing some contraction.”

Despite this, Chelsea wasn’t seeing a major hiring slowdown—until a couple of weeks ago.

How School Funding Impacts Education-Adjacaent Hiring

In addition to being hiring season, March and April are also the months when districts and individual schools typically set their budgets. Which is important to watch because school funding directly impacts hiring in EdTech and educational nonprofits.

“40% of North American EdTech is K–12,” Chelsea says, “meaning that 40% of EdTech funding comes from our local tax base… So what happens in the public school budget cycle impacts EdTech hiring.”

The influx of federal funding into public schools during the pandemic helped to propel the EdTech boom, with 92% of public schools using ESSER funding to purchase equipment and EdTech.

Conversely, the expiration of these funds means contraction.

“Everyone knew ESSER funding was expiring—you could budget for that, you could adjust your hiring. We’ve already been seeing a little less hiring over the last six months compared to the funding boom.”

Now, uncertainty in federal funding is exacerbating this trend.

“Unfortunately, we’re in a moment where we don’t know what’s going on with federal funding. We can’t guarantee the same level of funding, even if it’s contracted—it may still be pulled back.”

One place Chelsea is following this trend closely is in professional learning specialists and instructional coach roles. 

When a school purchases a company's tech product, they can choose a larger package that includes a dedicated customer success representative who helps the schools get set up, or instructional coaches who provide training for teachers and professional development. 

“Those professional learning specialists and instructional coach roles were often great bridge jobs [for teachers],” Chelsea says. “People would still be teaching, take the contract role for a year or two, and then move into a full-time role.”

When schools were getting pandemic-era funds, they were more willing to purchase these bigger packages—because they could afford it.

“I’m worried about what will happen with ESSER funding sunsetting—whether school districts will still be able to afford these roles because they are expensive.”

Educational nonprofits are also reflecting this uncertainty. Many nonprofits and STEM jobs are impacted by NSF (the National Science Foundation) funding. Since the beginning of the year, NSF has been pulling, freezing, and scouring grants to ensure compliance with Trump’s anti-DEI orders, “meaning people who expected grant money in January to pay their staffers aren’t getting it.”

How will all this impact hiring? 

“I think it’s too soon to say for sure, but I expect to see a slowdown, especially with nonprofit jobs. That’s where I think the impact will be strongest. The larger companies still have the capacity to hire and expand, but grant-funded positions are going to feel the squeeze.”

The Importance Of Relevant Skills

Feeling like you don’t qualify for any of the jobs you see posted?

You may want to look again—at the relevant skills section. 

“I've seen a shift in [companies] not really defining what kind of experience they're looking for,” Chelsea explains. “They know there are a lot of different people in the market. They know a lot of people are pivoting. So they’re saying, ‘Here are the key skills you need to have. If you can demonstrate those key skills, then we're looking to hire you.’”

That’s why it’s so important for educators to ask, "What are my skills?" and then look for jobs that match. 

“Instead of ruling yourself out because you ‘don't have assessment experience,’ ask, ‘What kind of assessment experience do I have? Does that line up with what they’re looking for?’ Look and see what the job is asking for before you say, ‘Oh no, that’s not me.’”

Chelsea recommends looking particularly at the relevant skills in jobs such as curriculum development, professional learning, PD, and coaching—which tend to match teaching skills the closest.

“Mentorship and coaching is one I think educators forget about, because a lot of more senior educators have mentored people every year for a long time. So that’s a skill that I think is really worth digging into.”

Also check out jobs in sales, account management, and customer service.

“A lot of times customer service isn't defined. So you can really think about, ‘Well, what does that mean?’ What they're really looking for is the ability to handle difficult customers, the ability to know when to step back, when to push a little bit, and just that ability to navigate complicated conversations.”

Chelsea thinks of these as functional skills—skills that are valuable across different job roles.

“That’s why I call them relevant skills—because it could be anything. And there are so many different ways that you could say, ‘Yes, I actually do have this experience.’ As long as you can define, ‘I can do the job because I've done it in this context,’ I would call that a relevant skill.”

The Types Of Skills Companies Are Looking For

The skills Chelsea consistently sees in job descriptions include program management, customer service (the ability to work well with people), and an understanding of the education market—knowing who the customers are, what their pain points are, and how to address them.

Program management, facilitation, and training skills are all important skills educators often don’t even realize they have. 

“The ability to clearly communicate complex information, understand how people learn, and adjust when they’re not learning—that’s incredibly valuable. In the workforce, you often get promoted because you have those skills. You might be hired for a specific role, but then people realize you’re highly effective, and you move up quickly.”

She also sees a big demand for soft skills such as organization and time management, which she says are valuable in almost every job.

Chelsea notes that educators “tend to be generalists in a way that companies appreciate. We do a lot of different things and do them well. I often see EdTech job descriptions that are looking for generalists who specialize in certain areas.”

These companies are pulling from a pool of educators with incredibly diverse skill sets. “While that might feel overwhelming to teachers transitioning out of the classroom, it helps to focus on the core functional skills that appear in multiple job descriptions.”

About Those Salary Ranges

Salary can be a tricky thing for transitioning teachers to navigate. After all, our salaries are set in payscale stone.

Chelsea advises not getting spooked by pay ranges. “Some companies post huge salary ranges. For example, I saw a posting recently that listed a salary range of $49,000 to $121,000. People see that and assume it’s unrealistic, but what the company is really saying is, ‘If we hire an entry-level person, they’ll make $49K; if we hire a senior-level person, they’ll make $121K.’”

While it’s annoying, it’s not necessarily a red flag—it just means the company is being vague.

“A bigger red flag is when companies expect excessive hours—like when they say, ‘Must be available to work more than 40 hours per week.’” Remember that outside of education, most jobs don’t regularly require you to work overtime.

Chelsea also recommends keeping an eye out for salary expectations that don’t match experience requirements. “If a company lists a salary range of $49K to $65K but requires six years of experience, that’s a sign they want to pay experienced professionals as little as possible.”

Not sure how much a company is actually willing to pay you? “Ask about it early in the process: ‘Given my experience, where do you see me in the salary range?’” Chelsea advises. “That can save you from wasting time on interviews for jobs that won’t pay what you need.”

Why Remote Work Is Here To Stay–In EdTech

EdTech—that hard-to-define industry that doesn’t officially exist—has always been remote-friendly.

That’s because EdTech companies often target the largest school districts where they can make the biggest sales—California, Texas, New York, Illinois, Georgia, Florida, to name a few.

“Since they’ve always been thinking nationally, it has never made sense for them to have a centralized headquarters,” Chelsea says. “A lot of EdTech companies were remote-first even before the pandemic.”

Even when thinking nationally, many EdTech companies also have location-specific remote jobs. “They need someone to sell in a particular area, and they’re not going to fly someone across the country every week—they’re going to hire locally.”

Smaller startups often don’t bother setting up physical offices at all. “For the most part, there’s no strong incentive for EdTech companies to require in-office work.”

All these reasons make Chelsea think EdTech is “uniquely positioned to continue being remote. I started tracking this in 2021, when the remote hiring bubble was growing and then coming down—but in EdTech, it hasn’t come down. I’m sharing more companies now than I was before.” 

Why Your Job Transition Is Taking Longer Now

It’s not just you—transitions are taking longer now.

“Switching careers has always been a long process, but during the ESSER funding boom, a lot of educators were able to move faster. Now, we’re returning to a more predictable hiring timeline, though it may be longer than before.”

How long are we talking? Chelsea estimates that a career transition now will take six to twelve months.

“The job market is tough, but that doesn’t mean you aren’t qualified. It just means this is a challenging hiring environment.”

One thing Chelsea doesn’t recommend: constantly revising your resume. “Sometimes, you don’t need to fix anything—you just need to be patient. Instead of reworking your resume endlessly, focus on networking, gaining skills, or simply taking a break.”

Another factor making job transitions tougher now is that there’s more competition.

“Teachers aren’t just competing with other teachers anymore—they’re also competing with former teachers who already have a year or two of experience in business.” AKA, all those folks who left in 2021-2022. Chelsea is currently tracking how many jobs are now requiring "two years of experience plus teaching.”

“We've had such an influx of teachers moving into the market, now an EdTech company can get somebody who has both tech and education experience. So there's a two-for-one there.” 

Despite the uncertainty and struggles of the job market, Chelsea remains confident that job transitioners can be successful. 

“Resilience is key,” she says. “Job seekers should focus on high-value activities like submitting strong applications and cover letters.”

Some patience will help, too.