Today we chat with Jay Lockwood. He was a high school science teacher before he got into sales. He’s now an Account Executive for an Ed Tech company and enjoys working with schools in this way.
We discuss his path from a BDR to an AE and all of the skills involved with sales, promotions and more!
Find Jay on Linkedin.
Free Quiz: What career outside of the classroom is right for you?
Explore the course that has helped thousands of teachers successfully transition out of the classroom and into new careers: The Teacher Career Coach Course
Listen to the episode in the podcast player below, or find it on Apple Podcast or Spotify.
Free Quiz: What career outside of the classroom is right for you?
Explore the course that has helped thousands of teachers successfully transition out of the classroom and into new careers: The Teacher Career Coach Course
Mentioned in the episode:
- Sign up for 7 days of free access to Orchard
- Use code “TCC” to get 50% off of everything at Aspireship
- Our career path quiz at www.teachercareercoach.com/quiz
- Explore the course that has helped thousands of teachers successfully transition out of the classroom and into new careers: The Teacher Career Coach Course
Episode Transcript:
Welcome back to today’s episode. We get to know Jay Lockwood, who is a former educator who taught high school biology. He now works in ed tech as an account executive. We discuss his transition out of teaching his new work life balance and how he stays connected to education. Hope you enjoy.
Elizabeth: Welcome back, everyone. We’re excited to have you for this next episode. And today we get to speak with and get to know Jay. Welcome, Jay.
Jay: Hi, how’s it going? Thanks for having me.
Elizabeth: Thanks for coming. I’m excited to get to know you. And we love to kick these off by hearing a little bit about your education journey, kind of, uh, what you taught, how long you were in education, and what kind of drew you to that profession.
Jay: So it is a, uh, I took the scenic route to teaching actually I went to school, I was pretty adamant about not wanting to be a teacher My mom was an elementary school teacher and I grew up in classrooms and I was like I don’t want to be an elementary school teacher. I want to do then it kind of blanked out at that point.
I just knew I didn’t want to be a teacher. Um, so when I graduated from college, I got into property management and it was a great skill to have, but it wasn’t very satisfying. and then I’ll randomly, all of my friends from college that I like, you know, went to school with, had classes with, hung out with, worked with, They all become teachers I was like, what are you guys doing? And they all became high school teachers and middle school teachers. And it was single subject at that point in time. And so I looked at what I was doing and like long term prospects, and it wasn’t very satisfied, um, and, looked into teaching. And at the time in California, um, around 2011 ish, they were looking for math and science teachers specifically.
And I love science, huge science nerd, hence my bicycle shirt. I wore that special occasion today. and, said, you know, I love biology and if I have an opportunity teach science to teach biology specifically, I will go for it. And again, there were, you know, California was looking for science teachers and biology is one of the, you know, in need subjects. And so I kind of dropped everything. My wife has a very good, stable job. And she was like, you want to change careers? Go ahead. You know, and so I quit my job, went to school full time and was able to become a teacher. And it was amazing. It was actually really a really great opportunity for me.
Elizabeth: That’s awesome to hear. And I love your shirt. And I, now, now I see you said PIEcicle, right? Yep. Nice. And so, were you in a private, a public, um, what kind of environment were you in with the High schoolers.
Jay: Yeah, so it was a public K 12 district in Southern California. it was a Goldilocks district. It was a great district. It was on the coast. It had, um, really supportive parents and a great admin, it was K 12, but it had four high schools. So we had like a large group of supporting teachers.
Like our cohort was very large. we were able to kind of like work with each other. Everybody got along with each other very well. My master teacher was at a separate school. and so we would talk all the time. So we collaborate all the time. our department was great It was very, very. Goldilocks ish, but yeah, but it was a public school and, you know, we still deal with the same kind of things you have to deal with when you have a public school.
Elizabeth: It sounds like very ideal teaching situations, which is great. Um, and so I’m kind of curious to know, you know, you’ve taught, you taught high school biology, and then you decided to pivot careers again. So what was that turning point where you decided you were ready for a change?
Jay: Yeah, so we ended up moving. Um, I moved out of Southern California. my wife’s career was going well and she was able to transition to, um, kind of remote work more or less. And she was tired of commuting. and then the pandemic hit and it was like, you know what, let’s pull the trigger and let’s move out of the area. And so I knew that I would be able to find another job teaching wherever we happen to go. I would just have to get a credential. And she was like, I feel kind of stuck. The commute is killing me, even though I’m transitioning to remote, but I might have to go back and I don’t want to do that. So if I’m out of the area and I’m on, I’m good at my job, I can stay, maintain remote. And I said, that’s fine. That’s not a problem. And so we moved, multiple States away. So it’s not an easy commute for her to try to get back to LA. So she’s like, Hey guys, I have to work from the computer now. that’s. Led me to kind of changing careers. The first year that we are at our current location, I didn’t work because I was in the process of getting my credential in my current state. And then I applied for a couple of jobs. one was the local high school, which is right down the street from me. And one was in a, another district about 20 minutes away and ended up getting offered a job at the district 20 minutes away, but here’s where the pivot comes in. It was a 24, 000 pay cut to teach the same thing.
And they were going to give me like years in service. and so I wasn’t going to be at the bottom of the pay scale, but it was a commute. And then I’d have to get my kids to my local school in time because my wife would have to travel and it was just such a big pay cut. And then I went and subbed at the school and it was a good school. It just wasn’t my experience at my previous district at my previous school. And I was like, you know what? I have such. A good, strong feeling about teaching. I don’t want to taint it I don’t want to take a pay cut. And so it was like those two things. And so I actually ended up declining the job, in a March and then went through Aspireship was able to get a job in August, um, as a BDR.
That was my first kind of sales job. That was a true remote tech sales job.
Elizabeth: That’s a difficult decision, especially, you know, I’m familiar with that. I remember when we moved from our place in the city and now we live a little bit more rural and, and when I moved school districts, the, there was just like an enormous pay cut, they would only take, you know, eight years of experience or seven, and then you, you kind of have to settle it, that pay scale, if you want to work in that.
So I can see how that’s, That’s difficult and I’m glad to hear that you got into sales and I’m also kind of curious, you know, how did you figure out sales? How did you find it? You know, how did you even find the Aspireship training and go into something like that from, cause I’m thinking, you know, you’ve got your biology background, your property management.
So tell us a little bit about how you made it through that path.
Jay: Yeah. So, so where I am, there’s not lot of higher level jobs unless you’re doing a trade. Um, you know, like my, guy who built my house and the plumbers and the electricians, they make a lot of money, but that those are skills that it takes years to learn. and a lot of those. tradesmen and women, they start when they’re, you know, 20 years old. I was running into this at 40 years old and I was like, I, my body can’t handle learning a new trade and going out and, you know, carrying lumber for a while. so then I looked at, you know, other potential jobs around here. Um, I asked, I looked at property management as well. And I was like, I’ve done that before. I no problem getting back into that. And again, the pay was very low. And so we started looking at remote jobs, like what we do from home or hybrid jobs or something like that. and then randomly through Instagram. I ran across teacher, career coach and a post by Daphne. so I followed that because I’m like, Hey, cool.
And, you know, she had some really good, you know, solid points of like your transitioning careers, you have skills you might not think of as transferable, they are, they’re definitely a lot more of the soft skills and maybe not the hard skills, but those are skills. You can learn the soft skills are developed over time.
And we’ve done that as teachers. and then from there, she had a, she had a, uh, of a link with Aspireship and I, you know, followed the rabbit hole and ended up taking the You know, entry introduction to sales course. I can’t remember what the name is. Um, but yeah, and that kind of led me here and it was a lot of the ability to talk to people.
And that was it. Like I truly liked connecting with my students. Uh, that was the most beneficial part of my Teaching career was, you know, being able to maintain a relationship with my students and help them and then move them along to the next step and make sure that they were set up for the next step and in sales.
You’re kind of doing the same thing. You’re meeting them where they are, them get their foundation, set them up for success. And then. Hopefully help them do better later on. And so it’s, it’s a, it’s a nice thing. I didn’t want to like maintain the relationship. And that’s one of the reasons I didn’t want to get back into property management because have this continuous relationship. I wanted to build a relationship and I wanted to set them on their journey. And that’s again, where, where the sales aspect comes in.
Elizabeth: And so as a, as a BDR, when you started in that role, you know, I know a lot of teachers are interested, curious, because there is kind of a pathway if you are a career pivoter to kind of get in this entry level way into an SDR or BDR way, and then kind of work your way up towards an AE. So can you talk a little bit about, When you first started was what did the BDR role involve?
Was there a lot of cold calling and how did you kind of get over that fear? If there was any fear of, you know, using your skills, that,
Jay: Definitely fear. There’s still fear, you know, it it’s, I, I feel more comfortable picking up the phone now, but still a straight cold call. You got to take a deep breath and be like, okay, get my mindset. the biggest pivot I think was learning how to change your messaging. So. Coming from a teaching standpoint, you kind of have a captive audience.
Like I hate to call our students captive audience, but they’re a captive audience. And so you have to adjust your message to get through to them and hopefully engage them enough to where they’re going to learn while they’re in the classroom. When you go into sales and you start doing cold outreach, you might be reaching out to somebody who has never even heard of your company before, has no idea.
So you have to kind of approach it from that point in time or that point of view, sorry, and say, this is. The role that I’m going to reach into, this is some common pain points. This is how we solve those pain points. Now go reach out to them. Um, and it depends on the area too. So you might be reaching out to California. They don’t pick up the phone, but you might be reaching out to Nebraska and you might get ahold of somebody. and you just have to, you know, work either email and multi thread and some LinkedIn and some cold, uh, you know, calling cold calling. it’s definitely a different. to approach your messaging.
You have to be very targeted, teaching, you can kind of be more holistic and kind of drill down. So like, here’s our foundation. Now let’s build back up. So you get the big picture, but I’m going to show you the big picture. And in sales, it’s, here’s your problem that I think I know you have. now I can help you build to that big picture because they might not even realize that can provide that big picture to them. And so that’s, that’s one of the biggest challenges. It’s kind of changing your messaging.
Elizabeth: that makes sense. And I like all the parallels to teaching too, and the similarities and differences. and now you’re an account executive, if I have that correct, and.
Jay: brand spanking new. Yes. Thank you.
Elizabeth: So I wanted to ask you about opportunities for growth. I mean, it seems like. Now you have grown into this new position.
So what does growth look like for you in sales and where do you eventually want to be? And tell us a little bit about like the next step of what an account executive does.
Jay: Sure, sure. So to kind of go back and say like, I’m going to SDR BDR position where I’m doing cold outreach. Your primary focus is to set meetings for the account executive. All right. So I’m going to be reaching out through email, LinkedIn, cold calling, trying to get a meeting, generate some interest, be like, Hey, this is what we do.
Is this a challenge you’re running into? Well, yeah, I’m really cool. Cool. Here’s kind of how we do it. Are you open to like learning a little bit more like a 20 minute conversation? And from there they say, yeah, I’m cool. And be like, no problem. No pressure. If it doesn’t work out, this is why we had initial conversation.
You’ll know more about us. We’ll know more about you and we can move on. After I book that meeting, my job more or less is done. As an SDR, as a BDR, it depends on like the different company, my previous company, got a small commission for setting the meeting. And then we got a percentage of the total sale.
So it was. It behooved us to, to set a, a good meeting. Like this is a true qualified lead. And if the AE closes it, we’ll get like 1 percent of the sale my current company. We get a higher base for setting. And then if it develops to, Hey, this is a good qualified lead. We get another chunk. We get like the second half of the commission, but I do not get a percentage of the sale. And so we didn’t really have, we don’t have, um, A huge investment after the initial meeting is booked. Yes. We still want to make sure that we get the rest of our commission by help setting a good meeting, but we don’t have an incentive to help along the deal. once it hits a certain stage, like there’s nothing we can do.
We don’t have the capabilities. as an account executive, um, I’m going to walk it from meeting booked all the way to close one or close lost. And that’s pretty much it. Where it’s going to be so engage not only my current stakeholders. I’m going to be holding a meeting with I’m going to have to talk to other stakeholders.
I’m going to have to find out who all the decision makers are. What do they need? in. I actually work in EdTech now. And so you have, and it’s primarily K 12 and public. You have a lot of different variances within there. So it’s a lot more confusing. sometimes it’ll just be, uh, like a district coordinator.
Sometimes it’d be the district director, sometimes you’ll have to get the superintendent. Sometimes you have to go all the way to board. there’s a district that we’re going to have to get the teacher’s union approval for. So it’s going to be much more varied, which is cool. It’s going to be interesting.
It’s like, okay, each of these is going to be different challenge. So you got to have to stay on your toes, toes. It’s not like, you know, click, send high, click, send high. It’s like, where are we in this deal with this particular client and how are we going to either help them or. Let them know we won’t be able to help them and that’s okay.
But now we are on the same page and we’re clear.
Elizabeth: That’s very interesting. And I’m glad you brought that up because a lot of teachers are interested in, in going into ed tech. And I’ve always kind of wondered because you are what I think, and what you’ve said is you’re selling to these school districts and then How do you access the superintendent?
Like, how do you access the board? And so, what a unique challenge, if you will. And can
Jay: sometimes it’s just straight cold calling them and be like, hi, I know that this is not priority for you. However, we can help with this part, you know, problem and take it off your plate. And they’re like, Great. And that’s great because you have this high access to power, they’re going to trickle down and they’re going to say, Hey, director of whatever you need to talk to this person.
I had a meeting. That’s that’s the other day where I sent an email to the director director looked at it, opened it, forwarded it to the direct. Sorry. Email the superintendent. They looked at it, forwarded it to the director. And the director said, Hey, my superintendent said, I need to talk to you.
And I was like, you sure do let’s go. And so, you know, it’s, and sometimes you have to work up cause you never get ahold of them and it just, is it going to work? You have to be not afraid to those extra steps and be like, well, this isn’t working, let’s try something else, you know, be willing to try new things.
And that’s it. If you’re willing to try new things, it’s going to work eventually. Um,
Elizabeth: us through the interview process, if you remember this process, um, for some of the teachers who are curious and interested, what it looks, what it looks like?
Jay: Yeah. So I’m going to have two BDR rules. I’ll talk about the very first one, the one that Aspireship kind of helped me out with, um, and I’m assuming your, your listeners are familiar with Aspireship.
Elizabeth: Yes,
Jay: Okay, great. Um, so they were able to set me up with the company. that was not an ed tech.
It was a market research company, a really cool company. that helped me get the foot in my foot in the door for the interview process. And then it was just being willing to ask questions. And that was a big thing is ask questions. What are we doing? How are we doing this? Like, what are some of the biggest challenges? That someone in my role would run into what do you see success looking like, for someone in my role, you know, three months down the road, six months down the road, 12 months from now. that was probably the. Biggest thing for me to remember was those interview questions, like assuming we are moving forward, what would success look like?
And at the very end, every single time I’ve gone through interviews, whether it’s an internal one for this AE role, whether it’s for this new ed tech company or for my previous role at market research, was what are your thoughts right now? what concerns do you have about moving forward?
And it’s just a temperature check and a lot of hiring managers like that. Instead of saying, no, I don’t have any questions. No, you want to have questions and you want to ask them, like, how do you feel right now? Do you feel comfortable with me moving forward with the process? Or is there anything I can clarify for you? because in sales, you want to do that. You want to definitely like disqualify the whole thing or when objection objections come up, you want to address those objections. And so you’re doing the same thing. You’re selling yourself to the hiring manager. And you want to make sure that we’re all on the same page. Don’t assume like, Hey, they liked me. This is really cool. And they’re going to call me back and then they don’t, you want to make sure that you’re setting up that next step Hey, do you have any hesitancies about me moving forward? What can I address for you right now? What questions do you have or what concerns do you have? I’m like, well, you know, you’re a little, I am thinking about X, Y, Z. Oh, great. I’m glad you asked that because here’s what my thought is. Does, does that kind of help clarify for you? Awesome. So the next step would be to to you in two days, or I will hear from this person in two days. I appreciate it.
Thank you for your time. Send a quick thank you note, and then go into LinkedIn and connect with the next person you’re going to, interview with.
Elizabeth: I’m glad that you said that because I feel like even if you’re not thinking about going into sales, if you’re a teacher and you’re listening, you know, you’re still selling yourself no matter what position that you’re going for. And I like that that before you get off the interview and. You know, I would assume it would work on a phone interview, too, that you’re, you’re asking for clarification next steps in getting a temperature check, so you have an opportunity to clarify or say anything before getting off the phone, because I think that is, that’s a great point, because it’s, it has become somewhat of a frustration when teachers apply, don’t hear anything back, don’t know what the next steps are, so I really think that’s a great tip for listeners just to try to implement that, When you’re, when you’re speaking with these people and, you know, I’m sure sometimes they’ll have feedback, maybe they might not have feedback, but either way you’ve kind of like cleared the, the basis for, for what’s next.
Jay: Yeah. I mean, it’s, you, you. interview process itself is a sales process, like no matter what interview you’re going to go for, what position you’re going for, it’s like you want to be a curriculum specialist. Let’s just use ed tech as a, you know, as a broad term, if you want to be a curriculum developer, curriculum specialist, or if you wanted to be a customer success person, or, you know, I’m going to go back and just be an accountant, no matter what you’re going to do is you’re selling yourself.
And so you need to take control. Of that interview process and you need to set next steps and you need to make sure that we’re all on the same page, you know, clarify, check for understanding lack of a better term right there, you have to do that. No matter what position it is, because again, an interview process is a sales process. You’re just the product and you’re the best product you can be.
Elizabeth: So tell us a little bit about, do you have, um, some favorite parts of this job?
Jay: yeah, when the calls go good. Those are my favorite parts. You know, that’s always the best. I do like being able to help. And that’s, I think why I got into sales is because a, I like to talk. I don’t like to hear myself talk, but I just like to talk and I like to be able to help. And I think that’s why I liked teaching was I was helping set my students up for the next S the next step success for the next step. And that’s what I’m doing currently. And that’s what I did when I was in market research, what I’m doing with ed tech. And if I move on, whatever the current industry is going to be, I’m here to help. And. That’s what I like is we can address issues and solve problems for clients and they’re happy and they can come back and be like, Hey, this worked really well.
Thanks. I appreciate you reaching out, you know, even for me right now, transitioning from my old rule when I would have somebody say, this is kind of what we’re looking for. I really appreciate you reaching out. Thank you. That’s great. That makes me happy. That like is my, you know, coffee after my coffee that kind of gets me going.
It makes me want to do the next style is just being able to help them.
Elizabeth: And can you walk us through, I know you mentioned earlier about, about what you do, but if just kind of like a typical day to day and you’re in your new position.
Jay: So in the new position, like I said, it’s brand new. it would be going to be prospecting all the time, so I would still be doing part of what I did. Um, it just wouldn’t be the whole day. I would still be reaching out the districts. I’m going to research districts. I’m going to say, like, they’re running into this, uh, issue. Here’s some of their test scores. Here’s how we can solve these things. So I’m still going to be prospecting and then reaching out to the superintendents, the directors, the coordinators, whoever I need to, then after that, it is going to be taking discovery calls and discovery calls for those of you who are not familiar is sitting down for like 20, 30 minutes with somebody truly finding what their pain points are and seeing if we’re able to solve them.
so getting on a call and you know, like, why did you take this call? Like, what are you, what are you looking for? You currently have this issue from what I understand. Is that correct? cool. And then just asking questions. As a kind of elaborate, you will find out. If we can help them, well, it sounds like we can help you out.
Would you be open to a demo and we can kind of demo our software and our curriculum and then move the process forward or what you’re looking for. I don’t know if we’re going to be able to solve, and say like, I’ve heard of this, the, here’s another option for you. this is kind of what we do. looking for this, here’s something that might be able to help you. And if anything changes, by all means, come back and reach out to me. so that’s going to be like a discovery call and then a demo. Um, like with our software engineer, you set up another meeting with more stakeholders. So say your directors, maybe a lead teacher, maybe, an assistant superintendent or something show the software itself. with different companies are different with my particular company. We have a sales engineer would be able to like really go through the nitty gritty of the software. And then I kind of sit back and chime in and say like, well, this is something they’ve talked about. Would you mind expanding upon? This part. Oh, yeah, great. We’re going to go over here. And so it just kind of the process. And then we go through, putting pricing proposals together. And then you gather information saying, like, you have this many students or you have, you know, this is what you’re looking for here. And here’s the different breakdowns that we can do, getting on a call there.
And then it’s. Finding out what the process is, um, from your stakeholders. The first person you talk to might not know the buying process. And so you have to like move up to the people who can sign the check, also who know that the buying process. So it’s just following, excuse me, following that particular account through and knowing what the buying process is. trying to satisfy every step as you go through.
Elizabeth: Thank you for sharing that. That’s very interesting. And I’m, I’d love to hear a little bit about your work life balance now. I know you mentioned, you know, no commuting, working remotely, but tell us a little bit about some of these differences.
Jay: Yeah. So, um, I don’t know if I’ll ever go back into a brick and mortar. I mean, if I have to, I have to, but working remote in my case is great. I have the ability to kind of set my own schedule and this is a sales specific thing. I don’t know about different. but if I don’t have a meeting and I have an hour and a half off, I can go get my car washed.
I can go drop off mail. Um, you know, at a certain point, like I go pick my kids up from school and I don’t have to send them to daycare. that’s probably the biggest thing is I can take my Children to school and come back and start working. I can go pick my kids up, drop them off at afterschool activities that we have set up for them or their home. I can continue working. I Have a setup kind of in the corner of one of my rooms. My wife has a setup in a different part of the house. We both work from home. it’s really nice that if I have something that I need to get working on, I can take a pause on it. I can have my family life and when the kids go to bed, I can go back to work for like two hours and be like, put my headphones in and just get it done because everything is here.
Everything I need will ever need is right here. or I can be like, you know what, I’ve got nothing today and it’s okay. I can, you know, spend a little bit more time with my kids. I can make sure that I start dinner early, you know, as I’m doing work, go out, do 40 minutes of chopping onions and, you know, get that cooking and then come back and finish stuff off. So it’s. It’s much more pleasant than you have to be here at 08:30 and you have to stay till 03:30 and if you’re not, you’re in trouble.
Elizabeth: Right. That’s great to hear that flexibility. And one thing you mentioned, I’m glad that you did is, you know, you said for your role, for your company. So that’s important to note too, you know, it can look different for the, the position, the company remote work. but I’m happy to hear that yours is pleasant and flexible, um, in your situation.
I’ve loved learning about your journey and I’m excited for everyone to listen. We kind of like to wrap these up by hearing about what you’ve learned about yourself during this career pivot process.
Jay: Yeah, no, that’s a great question. Thanks for asking that. Um, one of the, one of the biggest things I learned. Is that I have the ability to kind of grind it out, like in teaching, you’re constantly adjusting, you’re constantly thinking all the time. So you’re kind of exhausted at the end of the day in this particular role.
Sometimes you just got to put your headphones in and grind it out and you just got to do it and you’re like, Oh, I don’t want to do this. I don’t want to do this. And then you just have to do it. And that’s where you see success is you just need to grind it out. Cause that’s not a constant. You’re not constantly moving.
You’re doing one thing and you’re doing it well. And again, in a repetitive like an hour straight. And then you can kind of come up and breathe and just change and, you know, go get a drink real fast and come back. I have the ability to do that. And then in the process of looking for a new role, right.
I ran across a quote by I think president Obama. Yeah, it was him where somebody said, what does it look like, or how do you be successful? How do you define success in a person? And I’m paraphrasing this to death right here, but he more or less said, be somebody who can get things done. I’ve never heard that before, but it resonated so much with me.
And so that’s what my goal is. Like I was always somebody who, Hey, you do it and I can present it and I can make it look pretty, now it’s, I need to do it and then I can present it and make it look pretty at the same time, and it actually gives me more confidence because I built this. And then I can show you the nuts and bolts.
If we have to go back down and you have nitty gritty details, I’ve built this particular thing and I know exactly what I’m talking about before. We’d be like, that’s a great question. I’ll get back to you now. It’s like, Hey, that’s a great question. Let me show you. And so just working on that. It’s a little bit of mindset shift, but working on that.
Elizabeth: That’s great to hear. And thank you so much for sharing with us today, Jay. I’m excited for everyone to listen, to learn about sales and also, you know, selling yourself in the interview process. And I can’t wait to share. So we really appreciate you.
Jay: thanks for having me. I appreciate it. And good luck to all of you out there who are listening.
