Show Notes

For many teachers, leaving the classroom isn't just a casual choice—it's a personal necessity. Caelan Boone, a former 8th-grade math and science teacher, found herself in that exact position. Driven by a difficult political climate and the urgent need to protect her wife's health during the pandemic, she made the leap. In this episode, Caelan shares her incredibly practical and resilient journey: from her first edtech role at a curriculum company to navigating a mass layoff, all while earning a Master's degree in Instructional Design. Now a Customer Success Associate at Swing Education, Caelan provides one of the most actionable "how-to" guides we've ever had on the show for teachers who are serious about landing their first role.

• The "Uber for Subs": Caelan explains her company, Swing Education, an on-demand marketplace that connects schools with vetted substitute teachers, taking the lift of compliance and credentialing off of administrators' plates.
• A Transition Born of Necessity: Caelan shares her personal "why" for leaving the classroom, driven by the political climate and the need to protect her chronically ill wife during COVID.
• From Teacher to... Marketer? Discover how Caelan's first edtech job evolved. After starting in a support role, she earned her Master's and pivoted to curriculum design *and* marketing, all within the same company.
• Your Teacher Superpower: Caelan identifies the "soft skills" all teachers have in spades, especially the ability to manage diverse stakeholder groups (parents, admins, students).
• How to *Actually* Get Hired: Caelan's core advice for "noodling" teachers. She explains why soft skills aren't enough and gives a step-by-step plan to learn the *hard skills* (like Salesforce or Excel) from job descriptions using free tools like YouTube.

Episode Article

Caelan Boone loved teaching middle school. But as the pandemic wore on, she found herself at a crossroads many educators face—one where personal necessity outweighs a passion for the classroom. As a queer woman in a difficult political climate and with a wife who is chronically ill, the risk of in-person teaching became too high. Caelan’s transition to edtech wasn't just a curiosity; it was a necessity.

Her journey demonstrates the power of being "always a learner." She landed her first edtech role at MobyMax, a K-8 curriculum company. But she didn't just settle. While working, she earned her Master's degree in Instructional Design, which allowed her to pivot *within* the company. She moved from a support role to math curriculum developer and eventually even started running their marketing, writing blogs and press releases. Her story is a perfect example of how one opportunity can lead to many more if you continue to build your skills.

After navigating a mass layoff—a stark reality of the tech industry—Caelan landed her current role as a Customer Success Associate at Swing Education, an "Uber for subs" platform. Her job is a natural fit for an educator. She onboards school administrators, provides training, and acts as the "voice of our customers" to the product team, all skills she honed in the classroom.

When I asked for her advice, Caelan provided a powerful, practical roadmap. She confirmed that while edtech companies *know* teachers have invaluable soft skills—like managing stakeholder expectations and public speaking—that's often not enough to secure an interview. "What's really going to set you up and above," she advised, "is going to be able to have some of that technical knowledge." Her tip? Get on LinkedIn, follow the edtech companies you admire, and start studying their job descriptions. When you see terms like "CRM," "Salesforce," or "pivot tables" mentioned, "do your homework." Go to YouTube, find a tutorial, and get familiar with the concepts. That technical literacy, she says, is what will make you stand out and prove you're ready to make the leap.