Category Archive

For many educators, the job is more than a profession—it’s a calling. It’s a deep-seated desire to help others find their way. But what happens when you feel called to find a new way for yourself? This was the crossroads where Ivey Harrison, a former college counselor, found herself. Her journey from the world of school administration to a thriving …

For many dedicated educators, the career path leads to school leadership. But what happens when the view from the principal’s office isn’t what you expected? What if the daily demands of managing a building pull you further and further away from the instructional coaching that first inspired you? This is a common crossroad for many administrators, and it’s one that …

Every teacher considering a career change asks the big questions: “What’s next?” and “Am I ready?” But the most critical question is often the most practical: “How do I actually do it?” Moving from the classroom to the corporate world requires more than a desire for change; it requires a strategic playbook. In a recent episode of the Always A …

For educators considering a career change, a common question looms: Will my experience in the classroom and school administration truly be valued in a corporate setting? Or will I be starting from scratch? The answer, from those who have successfully made the leap, is a resounding affirmation of the unique and powerful perspective that educators bring to the business world. …

For many educators, the word “sales” can be a significant barrier to considering a career in EdTech. It conjures images that feel worlds away from the collaborative, mission-driven environment of a school. But what if that’s the wrong way to look at it? What if a role in EdTech is actually an extension of teaching? In a recent episode of …

The leap from school administration to the world of EdTech sales can feel daunting. The skills that make a great principal—managing staff, supporting students, and putting out daily fires—don’t always seem to translate directly to a sales quota. But what if that perspective is the key to success? In a recent episode of the Always A Teacher podcast, I spoke …

Okay, so the official title of this episode is “From The Principal’s Office to EdTech AE: How Jonathan Strout Redefined His Value,” and I have to admit, that doesn’t exactly roll off the tongue. We’ll work on it. Regardless, I recently sat down with Jonathan Strout, a former high school principal who made the courageous leap into the EdTech industry and is now …

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 …