A reflection for transitioning teachers
Why I won't be returning to the classroom this fall (and haven't for the last ten years).
Buckle up, friends—this one’s a bit long, but I hope it provides some helpful insights! Recently, Jeff Patterson shared a blog post by David Lockhart titled “The EdTech Industry is a Mess, I am Going Back to the Classroom.” While I appreciate David’s perspective and the valid concerns he raises, I want to offer some additional angles for those considering a career change.
Am I an expert in the career advice field? No. But I followed quite a similar career path to David. I taught high school history for four years before I transitioned into instructional design in higher education. After serving in the higher education space for eight years, I moved into the corporate edtech startup space and worked with an OPM and edtech SaaS tool. After three years in edtech, I have most recently transitioned into a non-edtech startup, something David mentions he struggled to do successfully. I hope this post can provide some hope and advice for you!
Why are you leaving teaching or edtech in the first place?
David mentions needing “a path to advancement, a path to advancing my family's fortunes, and a path to further my career.” If you’re seeking career advancement, it’s understandable. As a teacher, I often felt my career path was limited. Beyond becoming an administrator, what options are there? I’m not sure if David addressed how he feels about this particular aspect in the classroom, but there are numerous opportunities for growth outside of teaching.
For instance, during my eight years in higher ed, I progressed from instructional designer to Associate Director of Instructional Design. In my last edtech role, after two years, I was on track to be promoted from Customer Success Manager to Customer Success & Education Lead, but chose to transition out of edtech.
In contrast, my title in teaching remained unchanged for four years.
Do you want to make more money?
David also cites financial improvement as a reason for leaving teaching. In New Jersey, where teachers are relatively well-paid, this wasn’t a primary factor for me. While I did get a raise when I left teaching and have climbed the career ladder, the financial benefits are somewhat balanced out by less generous benefits compared to teaching.
Or is it something else?
Where I diverge most from David is in my primary reason for leaving teaching: I was overwhelmed, working nights and weekends, feeling unsupported, and burning out. Leaving teaching resolved this issue for me, even in roles where the workload was high. For this reason alone, I wouldn’t return to teaching.
What does stability mean for you?
David mentions, “One of the many reasons I started as a teacher was for stability, and I let myself get to a place where that wasn’t the case.”
Is stability job security?
If job security is your priority, this is a valid concern. The edtech industry, like much of tech, has seen significant layoffs in the past two years. While working in edtech during tumultuous times, I’ve learned a lot about the level of importance job security plays for me and developed questions to try and assess a company’s stability.
Interestingly, I was laid off after my first year of teaching due to state budget cuts (I did get rehired for year two after months of uncertainty), but I’ve never personally been laid off outside of teaching (knock on wood).
Is stability staying in one job with the same team? Does teaching offer that?
Staying in one role with one team is another way to define stability, and that’s valid too. David cites company acquisitions and team turnover as signs of instability in edtech. However, I faced similar instability in teaching, which contributed to my burnout. In my four years at a school, multiple levels of administration turned over, leading to constant shifts in job expectations. New systems, lesson plans, and processes made it hard to settle into a routine. I also felt unsupported as a new teacher. When my non-history department chair assigned me to mentor a student teacher during my third year, despite my concerns about my own preparedness, he told me it would be “good for me.”
How are you leveraging your resume and network for a new role?
David mentions, “I was also not in a transferable position. I did some of everything in the startup world... It meant my title was unique, which was great when I was happy, but it killed me in the EdTech job search.”
While I can’t critique David’s resume or fully understand what role he was seeking, I do recognize the challenge of navigating a wide range of responsibilities. I faced a similar situation in my edtech role, where I handled customer success, education/training, and onboarding. While it was initially confusing to identify the right job titles, I believe this challenge can be overcome.
How are you leveraging your experience on your resume?
Start by examining job descriptions that appeal to you. Identify the key responsibilities and match them with your past results. These outcomes should be the focus of your resume.
Provide context.
My title was “Customer Success Manager” at a small company, but that didn’t fully capture my role. On my resume, I added context by listing it as “Customer Success Manager and Customer Education at an edtech SaaS startup,” assuming most employers wouldn’t recognize the company name.
Provide outcomes.
I maintained two primary resumes:
A customer success-oriented resume highlighting metrics like GRR, NRR, logo retention, and product NPS.
A customer education/instructional design-oriented resume (which I used more often) focusing on metrics such as VILT sessions designed, academies developed, and course retention/NPS.
Simply listing responsibilities without specific outcomes wouldn’t have demonstrated the specific value I could bring to a role, or how my varied skills might transfer well.
Find a community and network.
David may have done this, but he doesn’t discuss it in his post, and I think it’s important to involve your network. Connect with people on LinkedIn for advice on entering your desired careers. Join LinkedIn and Slack communities, participate in events, and engage in roundtables. It was through a Customer Education community that I eventually found a role outside of edtech.
How can you examine new job opportunities?
David suggests considering two factors: 1) Is there long-term stability? 2) Is this a position that can quickly transfer to another company? In hindsight, he felt he should have answered “no” to both.
Is there long-term stability?
This is important when you’re considering joining a new company, especially a startup. But how do you gauge this? While I’m no expert, I’ve learned to ask specific questions during interviews to assess a company’s stability. If a company is unwilling to be transparent about their responses with final candidates, that’s a major red flag for me personally.
Here are some questions to consider:
What is your ARR (annual recurring revenue)? How dependent are you on incoming revenue versus outside investment?
What is your current customer retention rate?
If you’re not yet profitable, what’s your financial runway? What’s the plan for securing investment if needed?
What was your growth rate last year? Did it meet or exceed expectations?
What are your growth or sales goals for this year? Are you on track? If not, what’s the plan to adjust financially?
Have you had layoffs in the past? What packages were offered to those laid off?
Will I gain skills in this role that I can use to find other roles in the future?
Instead of focusing solely on how quickly a position can transfer to another company, think about the key skills you want to build. When interviewing, ask about professional development opportunities and how the role might support your growth in new or existing skills.
Final thoughts
When thinking about a career move—whether leaving teaching, transitioning within edtech, or exploring new opportunities—it’s important to reflect on what you really want in your next role. David makes valid points that are crucial for transitioning teachers to consider. But here’s the thing: both can be true. Edtech can be chaotic, but sometimes it’s still a better option than teaching and can serve as a stepping stone forward.
As for me, I won’t be returning to the classroom this fall.