Work History No. 3: A 33-year-old remote tech worker who left teaching due to burnout

It’s a challenging time to be a teacher in the U.S., from the long shadow the pandemic cast on students’ education to the nonstop politicization of classrooms. As a result, the teaching profession is experiencing its lowest levels of employment in 50 years, according to the U.S. Bureau of Labor Statistics.

Today’s featured writer left teaching for a full-time remote role at a tech company. Her story highlights some of the issues many teachers face: long hours, loss of identity, school politics, and burnout.

I’ll leave it to her to tell the rest of the story. If you’d like to submit your own anonymous Work History, you can do so here. We have a lot of great submissions, but we’re looking for more from women earning less than $100,000 per year.

- Alicia

The responses below have been lightly edited and condensed.

Age: 33
Location: Northern Vermont
Job title and industry: Operations manager, Software-as-a-service (SaaS) tech
Career length: 10 years
First salary: $33,250 in 2016
Current salary: $152,000 plus bonus

Biggest salary jump and reason for the jump?

I’ve had two significant salary jumps. The first was actually when I moved from teaching high school in North Carolina to teaching in Boston. North Carolina is one of the lowest paid states in the country for teachers, so I nearly doubled my salary when I made this move (of course, the cost of living also went up).

I had another significant salary jump this year when I was promoted internally from a customer success manager to an operations manager: I went from earning $110,000 plus an annual bonus to $140,000 plus an annual bonus.

Interestingly, my salary didn’t increase too significantly when I moved from teaching to tech because I was teaching in a fairly highly paid district in Boston. My last teaching salary was $76,000, and my first tech salary was $85,000.

Biggest salary drop and reason for the drop?

I’ve never taken a salary cut since I started working as an adult, knock on wood! I currently work in tech, which is a highly unstable industry, so I’m always steeling myself for a layoff that might lead to me having to take a pay cut.

What’s the most interesting part of your career history?

What most people are interested in is my transition from seven-plus years of teaching high school English to working remotely in tech for SaaS companies. That was certainly a huge transition in my life, but I also think my trajectory since getting into tech has been interesting, because I’ve moved fast to make this career what I want.

Since 2022, I’ve had four different roles at two different companies. I initially started as an operations associate but accepted a move into a customer success manager (CSM) role when it seemed like my other role might be eliminated. When I got another CSM role at a different software tech company, I made it my mission to get back into an operational role as soon as possible.

Why did you decide to transition careers? Was there any further education or credentialing you needed to do so?

One side of this answer is that I was really burnt out and just tired. I was the kind of teacher who always took on more and wanted to help everyone—I think most teachers are this way, truthfully—and continuously ran into frustrating political situations with parents and administrators.

However, the reason that is perhaps more important is that I realized I did not want my identity to be entirely about my career. Before, I was a teacher; now, I am a person who happens to work in tech. I needed more of my mental, social, and creative energy to be left over for me after a week of work.

I didn’t require any additional credentialing to make this switch, but I did spend a lot of time researching how to write my résumé, apply for roles, and interview in other professions.

Do you enjoy working remotely?

I love working remotely and hope I never have to go back. Actually, the brief period where we had remote learning during the pandemic was one of the inspirations that made me start looking into remote careers. The ability to go for a little walk in the middle of the day and hang out with my dog at home does wonders for my mental health.

Do you miss teaching?

I miss the students. Teenagers are so fun and constantly keep things interesting. At times, I also miss the creativity of lesson planning, but I actually do a lot of learning and development in my current role, which scratches that itch.

For me, the all-consuming nature of teaching (never being done grading, always having more to do, supporting kids going through really tough stuff) really outweighed all the things I loved about teaching. Unless there was a major paradigm shift in the way we operate schools in this country, I don’t think I could ever go back.

That said, I have recently started doing some virtual executive function coaching with three teenagers for a few hours a week in the evening, and it’s been a joy to work with them again in a small capacity. Mostly I’m helping them with staying on top of their homework and staying organized.

Best salary-related advice you've ever received?

Always ask for more money, yes, but also always ask for the extra stuff: a sign-on bonus (even if it’s just $5,000), more stock options, extra learning-and-development budget, the fancy office chair, or the extra PTO.

Often hiring managers and HR teams have much more leeway to provide these extras. Ask for them even after you get the job. Particularly coming from working in education to now working for soulless for-profit companies, I never feel bad about asking them to spend their money. I even applied this recently when buying a new car. They wouldn’t go lower on the price, but they would throw in a set of snow tires and a roof rack, which was a value of $1,500 total.

Did you ever need to bring money in on the side?

I’ve often had a “side hustle,” particularly when I was still teaching. I would wait tables or bartend on weekends, and I also worked for many years at a summer educational program, which paid between $5,000 to $9,000 for eight weeks of work.

Now I am doing the executive function coaching, and I typically see each of my three students twice a week in the evenings for 30 minute sessions. I’m paid $50 a session. In the past few months this has amounted to between $800 to $1,200 of extra monthly income. Of this, I set aside 30% for taxes, as they don’t withhold anything.

With hindsight, is there anything you would have done differently at any stage in your career/salary journey if you could go back in time?

I wish I’d had more education and information about the different types of careers that exist. Based on what people in my family did, I always thought that a helping profession would be the best option for me. But as I’ve worked in tech for longer, I think, with the right education, I would have thrived as a developer or designer. I never thought that kind of work was for me because I was always told I was creative and empathetic—but those skills can be huge assets in STEAM professions as well!

Anything else you’d like to share?

Coming from a “do-good” profession like education has given me lots of perspective on asking for my money’s worth. Teaching is one of the hardest, most skill-laden careers there is. It’s already such a joke that a teacher can’t even break $50,000 per year in many states in the U.S., while I can get paid $150,000 to sit at my computer and make Powerpoint presentations. (Even though I’m very grateful for that, especially with our first child on the way!)

Because I view all this tech money as an absurdity to begin with, it takes some of the pressure off of negotiating. Don’t get me wrong, I am very appreciative of my job and lifestyle, but I’m also quite cynical about the economic and social conditions that allow for such exploitation of care workers, and some of that cynicism leads to a “devil-may-care” attitude toward negotiation.

Work History

First job: High school English teacher
Starting salary: $33,250
Departing salary: $36,000
Years: 2016 to 2018

Throughout college and into my early twenties, I worked as a bartender and server at various restaurants. Typically the pay was about $2.50 hourly plus tips for those jobs. I was also a substitute teacher for $250 per day.

However, my first real job was as a high school English teacher at a school in suburban North Carolina starting in 2016. (It’s crazy to think I’d just graduated college in 2015 and was basically still a teenager myself.)

I remember just being thrilled about having a salary at the time. Plus, I’d taught in various capacities throughout college, and this was my dream job. With no major expenses or people relying on me at this point in my life, I don’t remember dwelling too much on the pay. I earned small annual pay increases.

Second job: Charter school teacher
Starting salary: $57,784
Departing salary: $78,919
Years: 2018 to 2022

In 2018, my now-wife and I moved from North Carolina to Boston, for a teaching job I had accepted at a charter school there. This school had a very clear salary ladder, which highly incentivized teacher retention between years four and eight.

I entered as a fourth year teacher at $57,784, and then, based on the salary ladder, earned $64,763 and then $69,919. In 2022 when I left teaching, I was earning $78,919, which included a small stipend for being my grade-level team lead.

Third job: Client operations associate at health tech company
Starting salary: $85,000
Departing salary: $90,000
Years: 2022 to 2023

In 2021, I began searching for jobs outside of education after extreme burnout from teaching through COVID-19 (not to mention disillusionment with the American education system). I was willing to do just about anything else, and in April 2022, I broke my teaching contract to accept a client operations associate role at a women’s health app.

This was such an interesting learning moment for me, as I was applying to noneducation jobs for the first time and really learning how to translate my skills into an entirely different world. I had two other offers at the time, which I used to negotiate the $80,000 initial offer to $85,000. Now that I’ve been in tech for a while, $5,000 really doesn’t seem like much of a difference; it’s funny how my perception of money has become so inflated.

I took on a lot of extra responsibilities in my first six months in this role and accordingly was able to advocate for a raise to $90,000 before moving to my next role at the same company.

Fourth job: Promotion to customer success manager (CSM) at health tech company
Starting salary: $99,500
Departing salary: $99,500
Years: 2023 to 2024

Staying at the same health tech company, I accepted a promotion after one year, and got a pay increase. I mainly accepted this role because the company wasn’t doing well, and I was nervous that my less essential client operations role would be eliminated.

As a CSM, I also received an annual bonus that was between 10 to 15% of my salary.

Fifth job: Customer success manager at SaaS company
Starting salary: $110,000
Departing salary: $110,000
Years: 2024 to 2025

I’d stagnated a bit at my first tech company and accepted my next offer from a SaaS company in a different sector in 2024, in the same role. The starting offer was $110,000, which they weren’t willing to negotiate, though I was granted a $5,000 starting bonus. I also received an annual 14% performance-based bonus while in this role.

Fifth job: Operations manager at SaaS company
Starting salary: $140,000
Current salary: $152,000
Years: 2025 to present day

After about a year and a half, I interviewed internally for my current role as an operations manager. The starting salary was $140,000 with additional equity, which I was quite pleased with and actually didn’t feel the need to negotiate.

I recently got a raise to $152,000 at my six-month performance review.

Looking back on my responses, it strikes me that I’ve been quite scrappy throughout my career. I’m always taking on something extra to make the salary I need or to move into the role that I want. If I’m not happy working somewhere, I have left. I’ve worked with folks who have stayed miserable in jobs for way too long, and my biggest advice would be to move on before it gets to that point.

Thank you so much! Please comment with kindness!