Leaving the Classroom: A Transitioning Teacher Podcast

Leaving the Classroom 42: Molly Schloesser Former Teacher 

In this episode of the Leaving the Classroom podcast, host Kristi Oliva interviews former teacher Molly Schloesser about making the transition from her career in education to new opportunities outside of the classroom. Molly shares her experiences teaching third grade for several years and deciding to pursue a change, as well as her ongoing job search as she works to transition into a new role in customer success or account management. 

On this episode Kristi shares: 

• Molly's journey from teaching third grade to working as an educational consultant for an edtech startup and then being laid off after eight months. 
• The challenges Molly faced in her initial job search after leaving teaching, applying to over 100 jobs before landing interviews and second rounds. 
• Molly's goals to transition from sales roles to customer success or account management and her long-term interests in business development while acknowledging the importance of gaining experience first. 

 Listen to the episode here:

Connect with Kristi on LinkedIn

Connect with Molly on LinkedIn

This podcast is sponsored by IDOL Courses and is the only authorized vocational school and implementation program of its kind that not only shows you exactly how to create your job application assets and build a portfolio from scratch, but also includes credentials, mentorship, expert coaching, and paid experience opportunities in corporate instructional design and online learning for life! Learn more about the program here.

Enjoy the podcast transcription:

Molly Schloesser 

Welcome to Leaving the Classroom. This is a podcast for teachers who are ready to transition out of the classroom and into a new career. Each week, I'll share stories about what I've learned moving from education to the corporate world. I'll answer the most common questions and share my best tips to help you get started. If you are considering leaving the classroom, this show is for you.

Kristi Oliva 

Hello, everyone. Welcome to Leaving the Classroom. I'm Kristi Oliva and I'm so glad you're here. Today, I'm talking to Molly Schloesser, a former teacher. Welcome, Molly.

Molly Schloesser 

Hi, there.

Kristi Oliva 

Hi, nice to meet you and see you and thanks for being on the podcast. I'm really excited to talk to you about how you got out of the classroom and just what your experience is like. So why don't we start there. You can tell me about your education background and what made you want to leave the classroom and then how you ended up getting out of the classroom.

Molly Schloesser 

All right, I have been... I was a teacher for about seven years continuously. I started off teaching after college and then stayed home with my own children for several years and then reentered the workforce teaching third grade. I also was a reading interventionist at a title one school and then returned to the classroom, job shortages, it's difficult to get specialist positions, especially when it comes down to things like title one funding. So I went back into the classroom, and that was in 2020, in August of 2020. So, mid-COVID and that was really a very, very interesting time to be going back into the classroom. We had one of those hybrid AB schedules. But my reason for returning to the classroom from being a specialist was because my own children were in a different school district from the school district that I was employed in. If you were teaching in the same district as your children, then your own children could attend school every day. They had a group of teachers' children that would hang out in the library, and they would do their remote work on site.

Kristi Oliva 

Oh, intersting.

Molly Schloesser 

Yeah, which was, I mean, that was a huge incentive for me to switch districts, but that led to me having to go back in the classroom. So, I did that job. I was back in third grade again, that's like, my niche grade. I just love third graders. And the first two years I was back in the classroom I was kind of getting my wheels turning again. But I pretty quickly kind of realized, like, Hey, you wanted to leave the classroom before for a reason. I'd pursued that resource position and I'd really enjoyed a lot of the administrative tasks that I was able to do and how I was able to support more schoolwide. Because I really like problem solving, and troubleshooting and so not having my own base classroom, let me help a lot more people.

Molly Schloesser 

So, I started actively job hunting to just completely leave the school system altogether, in the summer of 2022. I actually made it known to my boss at the beginning of the school year, what my intentions were because I'd started applying over the summer. Nothing had come through yet and I knew it had the potential to kind of be a long haul but if something came through I had every intention of taking it and leaving. Whether that was mid-year or whenever. I really, really value transparency and so I sat down with her at the beginning of the year and said, hey, this is my intention. This is what I'm doing. You'll get the 30 days notice that's required by the contract but just know that this is something I'm pursuing. She was actually really wonderful about it. Most leaders I have found really appreciate transparency. The last thing they want is to be blindsided and so she knew that this was something that might happen during the school year and so she could kind of get my help plan in place for if a teacher left mid-year at this grade level, what... how would they shift? What would they end up doing? So, I spent... probably it was a solid seven months of applying and interviewing before I actually left the school. It was crickets, absolute crickets for months and months and months. I got zero traction on any applications. Just kind of was like, am I yelling into space? Like, where is this going? Nobody is responding and I think a lot of that had to do with the market was difficult. There were a ton of layoffs last year so the competition was really stiff last year just as much as it is this year. And then also kind of needing more of a corporate eye to take a look at my resume and help me structure that and focus on... there's a lot of little details that go into crafting a resume that is readable for someone in the talent acquisition arena. Once I kind of started making some real adjustments to the way that that looked, then I started to get some more feedback from different companies. I ended up with a company called Begin, working in their tutoring department, Kid Pass Tutors. This is an Edtech startup and my job title was Educational Consultant. And so, that role was part sales, and part the consultation, the conversation with the parents themselves. So this was something that families would reach out to us looking for tutoring for their child, and it was one-on-one customized tutoring, you know, done online. My part in that would be to have a conversation with the parent and discuss their needs and trouble spots for their child, and then talk to them about how the one on one tutoring could positively impact their child's education. It was kind of like a little bit of both, you know, the trying to make sure that we got the sale, obviously, we want them to sign up. So a large part was sales. I had a commission structure and, you know, had goals to meet each month. And that was a whole new thing, like coming from just having been salary as a teacher. But it was proportioned such that it wasn't, you know, an overwhelming feeling of pressure, you know, because there's a salary component, and then there's the remainder, that's the commission structure. I actually ended up enjoying that at first. I was kind of like, Oh, what if something... what if I suck at this? What if this is does not go well? But it actually turned out to feel very natural, because I believe in education, and I believed that we could help, you know, these families and... who were reaching out. The parents that we're talking to are people that want to help their child. So, I wasn't trying to force something down their throat that they didn't need or want. We only called warm leads, which to me made a big difference. There was not just random cold calling of just any number that we could get a hold of. I actually really enjoyed it. I liked being on the phone and talking to these parents and listening to them is kind of like the parent teacher conference but without having the folder in front of you about the kiddo. You're relying on what the parents tell you to fill you in. And then you have to figure out okay, here's what you need, XYZ on the fly and I really like that. I really like coming up with solutions to problems and a variety of solutions and so I found it really enjoyable. So that's what I did last year. Yeah.

Kristi Oliva 

So, tell us what's going on now. I know that you've got a different mindset these days.

Molly Schloesser 

Yeah, so that was a whirlwind. It was really exciting to land this job and finish up, actually. It worked out really amazingly, because when I got the offer, it was right at the end of the semester, first semester for school. And I had enough leave, like a leave balance with the district that I actually... they just dissolved my classroom and spread the kids into the other third grade classrooms because their numbers were not so high. And they literally were like, Hey, let's just clean slate, end of the semester. So my class just instantly dissolved and they were like, you can just take your leave. You're just done and you can go start your...

Molly Schloesser 

It was just this crazy stars aligning thing for me last winter, and it could not have gone more smoothly, honestly. So I worked there, through... I started at the end of February, through this November. And I mentioned it was a startup and so they decided to phase out the tutoring branch of the company. The company itself is still standing but the online tutoring division has... is going away. And so me along with the rest of the team, we were laid off before Thanksgiving, and that was a whole new reality from having such job security with teaching. I knew abstractly, that it's a possibility that you can get laid off, you know that things just... but as a teacher, you have to just totally, egregiously drop the ball for something like that to happen. Right? And so I was kind of like laughably in shock when it happened. Like it didn't sink in for a few days. Like oh, no, really like you just got this job this year and now this job is gone. What are you going to do? And so, got right back to, revise the resume and remember the practical skills. I've learned a lot on LinkedIn, that's been my go to too but finding high quality people to listen to and get tips from. So there are you know, just a couple of people that I continuously go to when I need feedback. And so tweaked my resume again and made sure to put really good measurable data in my resume and just started applying. As of today, it's been about a month and a half. It was right before Thanksgiving. So it's been a month and a half, almost two months now and I have applied to probably over 100, for sure, jobs. And I'm getting significantly more traction this time around. A number of interviews, and even some second rounds. And I credit that to having exited the classroom and having gotten into the market, and now having this business and sales experience. And so, you know, at first I was like, just so excited, oh, my gosh, this is gonna be so much easier this time. I'm just like, No, you just, you made it to the next step. And you get that part but there's still so much competition. All these other people who've been doing this for XYZ number of years longer than you that still want the same jobs. And so that's where I'm sitting now is just keep hammering away at it. And it's a quantity thing when it comes to applying, make sure you're targeting the right jobs, and then as many of them as you can find. So I spend several hours every single day, looking for jobs, updating the cover letter for every single one that I apply to, updating the resume for every single one and it's my job right now.

Kristi Oliva 

Wow.

Kristi Oliva 

Yeah. So what kind of roles are you searching for? Are you looking for similar roles? What niche have you found that you think that you want to move into and stay in, in the corporate?

Molly Schloesser 

Yeah, ideally, I'm trying to step now from being that first line of sales into more of a customer success role or account management. So, handling the existing customers, and then trying to ensure that they renew. I think that that would be a good bridge for me of my ability to communicate with people. And then a little bit of the sales work that I did already, but slightly more stable. I'm not sure if that's the right way to express that, but...

Kristi Oliva 

Yeah.

Molly Schloesser 

That's what I want to transition into next, I think that'll give me exposure to a few more aspects of business. I think long term, I want to move towards something in like the business development realm. But I am in the.... I'm like the baby deer, you know, in the business world right now. It's just... still learning about all of the nuts and bolts and I think that there's really just no substitute for experience for a lot of that stuff. It can be intuitive for some people, but you still have to get the jobs and do the work to get up the chain.

Kristi Oliva 

So, I bet you a lot of people are going to be wondering this, and I'm wondering it myself is, first of all, have you considered going back to teaching? And does this decision, like what happened, does that make you regret leaving teaching?

Molly Schloesser 

It does not make me regret it at all. Yes, it's hard but I was so depleted. Going from getting up in the morning... and I have children.... and so feeling like just shot out of a cannon first thing in the morning. Up at the... it's dark out. It's pitch black. Elementary schools here in North Carolina, students walk in the building at 7:30am.

Kristi Oliva 

You left for a reason, yeah.

Kristi Oliva 

Oh, my goodness.

Molly Schloesser 

So teachers have to be on site before seven. Yeah. And so it was just like all systems go, crack of dawn, get my own kids out the house, get to school. And then you know, the life of an elementary school teacher, you don't get breaks. We didn't have coverage for recess and we didn't have coverage for lunch. The only break we had was when the kids would go to Art or PE or Music and even then it's planning time, it's not actually a break. And so the entire day was just this frantic pace, running from one end of the building to the other. And if you're lucky, there are not as many fires to put out that day so you can actually try to get ahead and be ready for the next day or the next week or whatever that might be. I felt like I was just... my heart was racing all day long and I couldn't even do the job as well as I wanted to do the job because it was like somebody would just always run. Then I would come home and as any human you need some... you need that time to decompress. You need some quiet but now I come home and I have my own kids and you have to immediately try to shift into... okay, what needs to be... how do I meet the needs of my family here at home? I was so drained, just overwhelmed and overstimulated from not having a single minute to myself the whole day. So no, I don't regret it at all because the shift in me. I'm a better parent for my own children having more balance in my life now. I am so grateful for that. And as difficult and frustrating as this is I have a really supportive family and they have really stepped up in this last few months because you know, job searching while you're still working is one thing. Job searching when you're unemployed is a whole other ballgame. And so they have really helped me not get too stressed about it. To your point about have I thought about reentering teaching... I thought about it for like this long. I went... I actually went and met with my last boss at the elementary school who was like... he was my favorite boss of all time. He was one of those leaders that actually makes you better at your job. They give you really valuable feedback, really constructive feedback that is timely. I really value his opinion. So I actually went to talk to him and he was like, Yeah, you know, we do have a position for you as a reading interventionist, if you want to do it, we can do it. You know, but he looked me in the face and he said, but doesn't really seem to align with what you want. And I just was like, it's not what I want. It's not at all. I don't want to be sitting right here having this conversation with you at all. But you know, I have kids to take care of. I have a house, like, there's real life. But he kind of looked at me and said... stay the course then. If what you want is what you had then stay the course. If it's still, you know, a couple months down the road, things are not looking great. This would be a unique thing that, you know, swing by, and maybe we'll be able to pull some contract work for you. But stay the course. Hang in there. Yeah, it sucks, you know, and then he talks about his brother inlaw, who seems to be continually unemployed, because he always works for various tech things and is constantly getting laid off. And you know, it's just the norm. And so it really helped me to have someone tell me like, it's okay, that you're in this place, it's a hard place to be and it's okay to be there. Just  keep going. Go through it, don't try to go around it, just go through it. And so that really helped because I was questioning gosh, do I just need to put aside what I want and get a job and just get back and do this. But I appreciated his insight on that. And it kind of makes me think of like, you know, so in dating or whatever, don't get back together with your ex, right?

Molly Schloesser 

There's a reason that it ended.

Kristi Oliva 

It's not gonna change.

Molly Schloesser 

Exactly. Don't go back. That's not healthy. Keep looking for what you want in life. You've got one life, you've got one shot to get these things. And so fight for what you want, and make your life the one that you want to be living. I have felt very optimistic and I had very realistic expectations going into the job search this time. Knowing how long it might possibly take, and just how much work it will be to actually get a job.

Kristi Oliva 

I mean, the good news is you already have some experience under your belt. I think that puts you... unfortunately for the other transitioning teachers, it does put you ahead of the game in that way. I remember when I first transitioned out, I got my first job and after that the job market was a little bit different. But I got more recruiter interest in general, just because I had stepped outside of the classroom, and they could just smell it, you know?

Molly Schloesser 

Yeah.

Kristi Oliva 

Now normally I ask, transitions teachers, what three skills any teacher has that would transfer, but I'm gonna give you an opportunity here to sell yourself. So tell us about your best teacher skills that have just been proven to transition so seamlessly outside of the classroom.

Molly Schloesser 

Okay, absolutely. The number one thing is the ability for a teacher to think on their feet. You don't have time to process what's happening all around you. It's just, hey, what's right in front of my face, this is an immediate need. I can handle this using whatever tools are at my disposal as well. You know, we're extremely resourceful people. And I think that we know how to get something done. We know how to get it done quickly. I many, many, many times found myself sitting with not enough work to do because I would do things so, so quickly.

Kristi Oliva 

So true!

Molly Schloesser 

We're so used to, we're so used to that, you know, being given something to work on, and just putting all our brainpower to it as hard as we could for a short period of time and just getting it done. Right? Because you just never... you don't know when the next fire is going to get lit. And, you know, I had coworkers having to say, hey, pace yourself. Slow down. It's okay. Like, but I enjoyed it. I enjoyed the fast paced nature of you know, being on the phone and talking to families but having to think quickly in the moment how to address their issues. I think those are probably the number one things that you can't have that kind of a response system unless you've had to practice it. You've been in an environment that has required that as a survival skill. And so it's definitely one of my greatest strengths at this point, like eerily calm when things get crazy. I'm just like, Okay, here's what we're gonna do. And it gets done.

Kristi Oliva 

I think those are really good ones. And I love that you brought up, you know, being able to just tackle problems. I've encountered the same thing at companies where they're like, oh my gosh, Kristi, like, you work so fast, like, how did you get that done so fast? And I'm like, How did you... like, why are you taking so long? Like, I don't understand.

Molly Schloesser 

Like, what were you doing?

Kristi Oliva 

Yeah, it's just constant. And, like, I remember, I've complained about how teachers have to work so much and I still bring this up. And yet I carry this into my new life but the difference is, I don't have the stress behind it. Like I still work crazy hours, but it's only because I choose to, and because I'm working on things that I have a passion for, like Leaving the Classroom. It's funny that that is something that I thought everybody had, like, I thought it was either you had it or you didn't. And really, teachers carry this into their new jobs. And so I wish employers knew that more. Because when you hire a teacher, you are hiring one of the most efficient, hardworking people that you will ever hire to your company. And it's something that I've gotten comments on multiple times at all three companies I've worked for since being a teacher. That's what they see and it's what's made me a really good program manager is that I'm really good at seeing through the crap and finding what's important, filling out the efficiencies for those... building processes so that I can just set it aside because that's what we have to do as teachers, we can't keep doing the same thing over and over. So we're like, okay, how can I build a process for that? You're a project manager already as a teacher.

Molly Schloesser 

Yeah.

Kristi Oliva 

I think that's so fun to see teachers be successful in these roles and be so successful. Like, it's crazy, because we have such transferable skills.

Molly Schloesser 

Yeah, the project manager, program manager, field, it interests me. It's so competitive. And so that's, you know, another one of the like, well, I could go this way or this way. But first, let's start at the foundational levels of business and learn how these companies work. What's at the bottom? I think that's such an essential thing in any organization. Some of the best people that I've worked with in the schools are the people who started out as a sub, and then they were a TA, and then they were a teacher, and then they were an interventionist, and then you know, maybe they're an admin, because they understand how it all works. And they know just how hard everyone is working.

Kristi Oliva 

And then I'm sure you've had the opposite. An admin, that's never been a teacher and that's been one of my worst experiences was working for an admin that was never a teacher.

Molly Schloesser 

Yeah, it can go both ways. In the right hands, if they are empathetic enough, and they have a good business mind, they can turn that school into a dynasty.

Kristi Oliva 

True. If they can trust the teachers also, I think that's huge.

Molly Schloesser 

They have to inspire those teachers to follow them though and that's rare. That's a rare gift. In general, the teacher who tries... Or the administrator who tries to run the school like a business without understanding their teachers. It's a sinking ship.

Kristi Oliva 

Yeah, that's so true. Well, what's the best way to get in touch with you? If somebody hears this and says, Hey, I've got a role like that or woud like to reach out. I've got connections, how can they reach you?

Molly Schloesser 

I'm on LinkedIn, Molly Schloesser. Email is perfect.

Kristi Oliva 

Awesome. Well, thank you so much for joining me, Molly. It's nice to meet you and I'm definitely gonna be looking at your journey and following along and seeing what you're up to next.

Molly Schloesser 

Thank you. Thank you so much for having me. I really enjoyed this conversation.

Kristi Oliva 

No problem.

Kristi Oliva 

Do you want to leave the classroom but you're not sure where to start? You can take the free Leaving the Classroom Career Quiz idolcourses.com/leavingtheclassroom. It's time to take control and make the career change that will change your life. It changed mine. See you next time.

Kristi Oliva 

That's all for this episode, but you can find more at idolcourses.com or subscribe to the podcast. And if you are ready to leave the classroom, use my code classroom100 and get $100 off enrollment to IDOL courses Academy.

Send your stories or questions to [email protected] or share them with me on Instagram @leavingtheclassroom.