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EP 03 Claire Bossert: From the Classroom to Educational Technology

In this episode, I’m interviewing Claire Bossert, a former teacher who transitioned to a new role after 8 years of educational experience. Claire recently was hired for a position at an education company after working as both a classroom teacher and a reading specialist. Make sure to stay tuned until the very end of the interview and hear how Claire decided on this specific career path.   

Listen to the episode using the podcast player or subscribe on Apple Podcasts or Spotify! The episode transcript is available below.

DAPHNE WILLIAMS: 
Hey, Claire, thank you so much for joining us today.

CLAIRE BOSSERT: 
Hi! Good to talk to you again.  

DAPHNE WILLIAMS: 
So, Claire, you were one of my students in The Teacher Career Coach Course, but I want to get back to the beginning like we’re just getting to know each other for the first time. So, tell me a tiny bit about your journey in education. Why did you become a teacher or how long you were a teacher? 

CLAIRE BOSSERT: 
So, I was in the school as for about eight years. My undergrad is actually in business and I worked that for… worked in marketing for a couple years out of school and just wasn’t totally feeling fulfilled. So, I started doing some volunteering at a shelter with a reading program and I loved it. So, I’m like, “Oh my gosh, I’m like meant to be a teacher. I need to be in the classroom.” So, I went to grad school and while I was in grad school, I worked as a TA, got my initial license, and taught second and third grade. Started kind of feeling a little frustrated in the classroom and loved teaching reading, so I went got my reading certificate and then was a reading specialist for the last couple of years. So yeah, in total, about eight years in the schools. 

DAPHNE WILLIAMS: 
Did you find yourself liking or disliking some of those positions more than others? 

CLAIRE BOSSERT: 
Classroom teaching is, I will say it, I think, until the day I die, the hardest job that anyone can ever have. It takes everything out of you and you put your whole self into it. Super rewarding, but also super exhausting.

I loved teaching reading, my reading specialist… My time as a reading specialist was super rewarding as well, but it came to a point when I knew I wanted to see what else is out there. 

DAPHNE WILLIAMS: 
What job do you actually do now? 

CLAIRE BOSSERT: 
I was hired as an Inside Sales Associate within a tech company.  

DAPHNE WILLIAMS: 
Okay, what does that mean?  

CLAIRE BOSSERT: 
So, my role, pretty much day to day, is I build relationships with districts and schools and work with them- looking at data and demographics and try to figure out what online solutions would be best for them.  

DAPHNE WILLIAMS: 
So, you’re kind of picking out the curriculum that would work best for specific school districts? 

CLAIRE BOSSERT: 
Yep.  

DAPHNE WILLIAMS: 
How did you decide on that career direction?  

CLAIRE BOSSERT: 
Well, I kind of made up my mind that I was ready to leave the schools and signed up for an amazing The Teacher Career Coach Course that kind of led me to realize that just throwing my resume out into every open position I could find was not going to get me to a place where I was happy in my professional life. And I started researching different jobs that I thought sounded interesting and trying to talk to people that worked in those positions to see actually what their day-to-day was and if they were happy in their new position. At that same time, I started looking for different companies I thought I might want to work for and ultimately, through that process led me to find my job now. 

DAPHNE WILLIAMS: 
What kind of jobs were you applying for when you’re just kind of throwing them at the wall? Just curious. 

CLAIRE BOSSERT: 
I don’t know, anything and everything from an admin assistant to… I don’t know, I feel like it was a lot of administrative work because I felt like “What can I do?” you know, my only skills are in the classroom. But again, through the course, I realized how transferable those classroom skills really are to a lot of different job opportunities.  

DAPHNE WILLIAMS: 
Yeah, and that’s, you know, it’s going to be different for every single person with everyone’s personality. There’s a former teacher that I’ve been working with and she’s in love with the idea of being like an admin assistant, or an office manager, or a virtual assistant, because she said, she just doesn’t really want to think or look at curriculum anymore. But, she really likes organizing things and she really likes data, but she also is kind of so burned out mentally out of it, where she doesn’t want to be in charge of presenting to anybody or having, you know, too much responsibility where she’s at the front of an office. 

She knows what exactly she would be good at. She would be motivated with, so some people would love those positions. It just, you know, it varies. I was also very much when I was leaving the classroom, I think, throwing my resume at anything that was out there for a little while. There were one or two job interviews that I had, where I thought, “Oh, I really hope I get this” and then looking back, I was like, “well, I may not actually like that…” but it’s such a good learning process because you’re not going to know until you start exploring and doing. I wouldn’t know any direction that I would need to go on if I didn’t put like that first step out there. 

CLAIRE BOSSERT: 
Definitely. I think it definitely depends on where you’re at with your job searching process, but for…  in the beginning, I was just like, I just have to get out. I will take whatever position it’s going to be that gets me out and that will be just like my stepping stone, but I’m really glad I ended up where I am because I think that I would have gotten bored really easily if I would have just taken whatever random job may have been offered to me. Whereas I ended up somewhere, it’s still in education, so I still get to work towards helping students and helping teachers. And it’s challenging and I’m learning, so I’m really glad I ended up where I am. 

DAPHNE WILLIAMS: 
What obstacles do you feel like you had to personally overcome to land this position? 

CLAIRE BOSSERT: 
I think confidence was a huge one. Like I said that I just felt like all my skills were classroom and I just couldn’t imagine why anyone would want to hire me being that all my experience was in teaching. And through different conversations with other teachers that had left that are in new roles and, like, I keep going back to it, the course really helped me to believe in myself that I did have skills that were totally transferable and that positions outside of schools we’re going to see as valuable.  

DAPHNE WILLIAMS: 
Yeah, that’s the main reason why I wanted to make The Teacher Career Coach Course because I felt the exact same way. I felt like no one wanted to hire me, I thought it was going to have to start all over again, and then once I finally got out, I started networking. I started looking around and seeing, no, there are all these natural career paths, but I was in my education bubble that I didn’t know anyone who had taken those paths. And so, I wanted to help open everyone’s eyes to the potential of, you know, there are all these other people out there.

You know there’s that statistic that says how many teachers leave, but what we always focus on is how sad that is, and it’s tragic, and something needs to change in education to help support people and to help make it more of a sustainable career.

But also, all those teachers go somewhere, you know, there are employers that are hiring the majority of them and some places like the ones that I teach in the course, hire… they hire more teachers than other positions just due to the natural transferable skills that come with education.  

 
CLAIRE BOSSERT: 
Definitely.  

DAPHNE WILLIAMS: 
Did you think before you took The Teacher Career Coach Course that you’re going to have to go back to school if you wanted to get into a new career? 

CLAIRE BOSSERT: 
Definitely. I was already looking at different certifications that I could get, you know, do different jobs, or…. Yeah, I definitely that was a possibility. I didn’t want to. I felt like I have a decent amount of education and I came to realize I have a lot of skills that different companies are looking for, but it did cross my mind that I might have to go back to school.  

DAPHNE WILLIAMS:  
Did you feel like you were qualified for this position when you were looking at the job description? Did it say that it was looking for a former teacher or during the interview process, did they give you any clues that your teaching experience was valuable? 

CLAIRE BOSSERT: 
It did not say that they were looking for former teachers and the requirements didn’t necessarily align, but once I got to the interview, it was kind of insane how easily I answered every single question with different things that I had done in schools. 

DAPHNE WILLIAMS: 
Yeah, especially educational companies. I’ve noticed a lot of the positions don’t require you to have educational backgrounds, but when you do, it almost gets your foot in the door even more because you’re able to speak to the customer. Is that kind of similar to the experience that you had in the interview? 

CLAIRE BOSSERT: 
Absolutely. I, you know, can talk the talk and I think I totally proved that in my interview. And it has been super helpful in my job now that when I call different districts and schools and I talked to principals, I can see myself in their school using this curriculum, so I can speak to exactly what they’re needing and looking for and wanting to use it for. 

DAPHNE WILLIAMS: 
Yeah, one thing that happens in interviews, also, is we always tried to be super, super professional. But there are companies that are looking more for, you know, personality over it. Did you have any experience like that with this interview?  

CLAIRE BOSSERT: 
Yeah, I feel super lucky to be where I’m at because the company really, like, prides itself on hiring good people and they’re willing to train you. So, they, in the interview, they want to get an idea of what kind of person you are not necessarily your background and your experience. 

DAPHNE WILLIAMS: 
Yeah, so they’re looking more for how you would fit within their company culture than necessarily someone who’s faking being overly experienced or a robot.  

CLAIRE BOSSERT: 
Absolutely.  

DAPHNE WILLIAMS: 
So, how does your new career compare to your experience as a teacher? Do you feel like you have any more work-life balance or if the salary is more or less, feel free to say so?  

CLAIRE BOSSERT: 
So, my work-life balance is completely balanced. Now, I feel like when my workday is done it’s done, and I’m not, I don’t have to think about it throughout the night. I don’t have to check emails; I’m not having dreams about things I could-have, should-have done. I have more energy; I feel more mentally and physically healthy. It’s just like, insane. As far as salary, I will say that I am more financially comfortable than I ever had been or probably would be as a teacher even with a second job.  

DAPHNE WILLIAMS: 
When you were you were a teacher you had a second job? 

CLAIRE BOSSERT: 
Correct.  

DAPHNE WILLIAMS: 
What was your second job? Do you mind me asking? 

CLAIRE BOSSERT: 
No. I, well, I did all kinds of things. I pretty much always taught before or after school. I did some adult education at a community college. I worked for a nonprofit. I just always needed something supplemental. 

DAPHNE WILLIAMS: 
Because your teaching salary wasn’t really making the cut for you? 
 
CLAIRE BOSSERT: 
Correct.  
 
DAPHNE WILLIAMS: 
That’s one of the more unfortunate things about teaching is it requires so much, you know, so much of your time and your energy and background. But then when it comes to financial stability, teachers often have to find themselves working even more on top of it. And you know, until things change, that’s going to be an unfortunate reality that pushes a lot of teachers out. 

CLAIRE BOSSERT: 
That was a huge frustration of mine. 

DAPHNE WILLIAMS: 
I mean, this is going to be different for every single person, but when you are leaving and got into this new position, do you already have, you know, benefits set up in this new position? How did that work for you? Because that’s a question a lot of teachers end up having, you know, what’s going to happen with my retirement? Do I roll it over? 

CLAIRE BOSSERT: 
Okay, so I work in a state or I taught in a state that requires or mandates you to give a certain percent to your retirement and that percent is insane. Anyone I’ve ever told is just like, “They can’t make you do that?” And I’m like, “Yes, they can and they did.” And so when I left, I rolled it over into just another retirement account that I had already set up. 

DAPHNE WILLIAMS: 
Oh, okay. Yeah, that’s, and that’s something I always tell people, I’m not a financial advisor.  
So, I know that because you were taking the Teacher Career Coach course, I remember when you actually got this position. It has only been a few months, but you did I think you sacrificed your summer to go into it, right? 

CLAIRE BOSSERT: 
Correct. 

DAPHNE WILLIAMS: 
Do you regret that decision at all? 

CLAIRE BOSSERT: 
Not at all. I mean, we’re obviously living in very weird times in a global pandemic, where I wouldn’t’ve really had a summer this year anyway, but the amount of PTO I get and the freedom I have once I clock out at the end of the day is just way more beneficial than, quote-unquote, “getting the summer off.” Because we all know, as teachers, we don’t really get it off. 

DAPHNE WILLIAMS: 
Have there been moments since you’ve started this new position where you’ve struggled with imposter syndrome where you felt like maybe you’re not good enough for your new position? 

CLAIRE BOSSERT: 
Definitely at the very beginning. It just feels weird to be out of the schools once you’ve left, but I can’t say enough how lucky I feel to be where I’m at and I actually got to start with a cohort with a couple other people at the exact same time and one of the other people I started with is also a teacher. So, we’ve definitely connected and shared how… it feels so weird to be out, but we are, just, feel so happy and lucky that we are where we’re at. 

DAPHNE WILLIAMS: 
Yeah, that’s a really great point. When you leave and you get into like a larger organization, especially an educational company, you’ll meet all these different departments that have former teachers but in different roles. Can you tell me some of the other position titles at your company that are taken by former teachers? 

CLAIRE BOSSERT: 
Sure, I can speak directly to a lot of things with that question. So, when I first found this company, through my research of places I thought I might want to work at, I reached out to my network and asked, “Hey, does anyone know anyone that works here? If so, can you put me in contact?” And I’m a part of this volunteer organization and one of the women in it connected to me to her friend who worked for this company, so I kind of shot her an email. 

“Hey, my name is Claire. I found this company. I want to know what it’s like. Do you like working here? What’s your role? I’m a former teacher. Do you have any suggestions on how I should approach the application process?” She was super helpful and came back and said, “I’m also a former teacher. You know, I left however many years ago. I am so happy. I’ve grown so much here. There are opportunities for promotions and different training opportunities.” 

Her role, I believe now is some sort of project manager and she is just killing it at our company, it looks like. 

DAPHNE WILLIAMS: 
When people are looking at that word project manager or that position title “project manager”, it’s usually so vague that it’s… it’s hard to understand what it means, but when it’s at an educational company, a project manager usually is just talking about an educational product. So, think about one piece of curriculum that you love and how would all the different departments put together that book. Like, who would put together the graphic design for the book? What type of text should be in the book? What are the assessments look like in the book? What kind of coding would have to happen? And they just have all the different departments create that and so, project managers at educational companies are often former teachers. 

CLAIRE BOSSERT: 
Yep, those skills are just so transferable. I think, day to day in a classroom, your project managing, you know, the whole day. So, it would make sense that a former teacher would do on that kind of role.  

DAPHNE WILLIAMS: 
What’s the first thing that you would advise a teacher to do if they were interested in pursuing your specific career path? 

CLAIRE BOSSERT: 
I would reach out to someone in this role and get an idea of their day-to-day and see if that was something you’re interested in.  

DAPHNE WILLIAMS: 
Yeah and, I know, that’s kind of hard, too. If you ever feel like you’re completely burned out sometimes you just talk yourself out of anything sounding good. Do you feel like you were ever at that low point during your career transition? 

CLAIRE BOSSERT: 
Yeah, I think it’s way easier to talk yourself out of something than to talk yourself into it. And that imposter syndrome thinking that you can’t do anything other than work in the schools. But it’s just proven to me time and time again that that is so not true.  

DAPHNE WILLIAMS: 
What was it about this path that really clicked with you that made you want to give it a chance? 

CLAIRE BOSSERT: 
I think talking with other former teachers that had left and hearing how happy they were. 

DAPHNE WILLIAMS: 
One thing that I always think is, you know, if your rock bottom not happy right now… I hate the phrase like, “what do you have to lose?” But you’re not really going to know what is out there unless you actually start exploring and trying and so… Fear can’t hold you back of “what if the next thing is actually worse?” because if you’re at the lowest, it probably won’t get worse, but it’ll help you move towards a different direction or get more clarity on what you’re missing in one situation. 

CLAIRE BOSSERT: 
Yeah, I mean, I can also speak to that. Another reason I left is just, like, there was no more room for growth. 

DAPHNE WILLIAMS: 
I think some people thrive with change. I really think that some people thrive in an environment where they’re able to change their day to day and if they haven’t explored positions with that environment, they don’t know that that’s the type of jobs where they thrive. 
 
CLAIRE BOSSERT: 
Right. 
 
DAPHNE WILLIAMS: 
A lot of people go into teaching as one of their first career paths. Is that how you were, also? 
 
CLAIRE BOSSERT: 
No, actually because my undergrad business, so I worked outside of education for a while. 

DAPHNE WILLIAMS: 
Did you like business or education more? Just curious. 

CLAIRE BOSSERT: 
I don’t know. I mean, they both had their, you know, pros and cons. 

DAPHNE WILLIAMS: 
But that, I mean, it’s fair, it’s really important, to be honest…. But, I think that your business and your education experience was a perfect fit for what you’re doing now. 

CLAIRE BOSSERT: 
Totally. So, when I started looking, I was like, “Hey, how can I combine these two backgrounds?” And this role is just the perfect combination of both. 

DAPHNE WILLIAMS: 
Yeah, absolutely. For me, I just, I never regret even the very last year that I had teaching where it was really not a pleasant experience. I had a very toxic work environment and just a lot of mental health struggles on my side trying to navigate that school year. And I’m not proud of, you know, how I handled some of the stress of it, but I would never change it for the world because that experience is… got me to who I am like now.  

CLAIRE BOSSERT: 
Absolutely. 

DAPHNE WILLIAMS: 
My experience and education helped me pivot and get into educational consultant, get into instructional design, get more confident speaking on stage, and I wouldn’t have ever done any of that if it wasn’t for that last year teaching even though it was really not ideal. 

CLAIRE BOSSERT: 
Yeah. Something I will say is that in when you are a teacher and you work in a classroom, you think you just work with kids all day, but I actually learned a ton of communication skills working in a school because there are tons of different personalities within teachers that you have to learn how to work with and communicate with and that in itself has been super beneficial outside of schools, too. 

DAPHNE WILLIAMS: 
When I’ve been working in different school districts as an educational consultant, I can identify different types of educators and it helps me, “oh, this is an educator who’s really into this kind of pedagogy and she might be more inclined to have interest in my conversation if I do this. But, this educator seems like she’s really busy and I can help her in this way.” And I always I thought of different people back in my school experience.  

Well, thank you so much for taking the time to be here today, Claire. If there’s someone who’s struggling right now, who has been putting out resumes and not hearing back from anybody, did you go through any times like that when you were applying? 

CLAIRE BOSSERT: 
Oh, definitely. I can’t even count how many resumes I put out there.  

DAPHNE WILLIAMS:  
What would you tell that person? 

CLAIRE BOSSERT: 
Try to narrow your focus find out what you think you actually really would enjoy doing and keep applying. Also, keep talking about it. I felt the more that I told people my plan, the more it became real for me. 

DAPHNE WILLIAMS: 
Yeah, absolutely. And every single person who’s applying and not getting the response that they want, or interviewing for jobs that they want, but getting “nos” after the interviews, you know, it feels so devastating, but the yes is right around the corner.  

CLAIRE BOSSERT: 
Definitely.  
 
DAPHNE WILLIAMS: 
Thank you so much for being here today and I really appreciate you coming and speaking to the audience. I know that they’re going to learn so much from you. Is there anything else you wanted to add? 

CLAIRE BOSSERT: 
No, it’s always fun talking with you, Daphne. 

I’m so grateful for all of the former teachers like Claire who have volunteered their time to help support The Teacher Career Coach community with their advice.  

Because Claire was a member of the Teacher Career Coach Course, I’ll link the course to the show notes of this episode for anyone looking to get started with my program. 

As always, please make sure you subscribe to stay tuned and leave a review to help other teachers find this support and community. 

Thank you so much for joining us and I’ll see you on the next episode of the Teacher Career Coach Podcast. 

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