In this episode, President and Chief Content Officer of Westchester Kevin Gray shares what EdTech companies are looking for in contract and freelance position candidates.
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Contract Positions in EdTech
Daphne:
In this episode, I am talking to Kevin Gray, the President and Chief Content Officer of Westchester Education Services, a B2B product development company. Westchester helps ed tech and ed publishing companies create market-leading curricular materials in all major subject areas. I’ve actually worked with Kevin to help him find the best candidates for his freelancing positions, and some of his full-time positions at this company.
In this episode, you’re going to hear almost what you would hear in these behind closed doors conversations with myself and hiring managers so that you can hear what they’re specifically looking for and how to stand out. In this specific episode, we’re going to focus on contract work for freelancing positions in ed tech companies.
Hey, Kevin. Thank you so much for being here today.
Kevin:
Yeah, thank you. Thanks for having me.
Daphne:
I know we’ve had quite a few conversations off of the podcast in the past before, but I would love if you just did a brief introduction to my audience so that they learned a little bit about you and your role at Westchester Education Services.
Kevin:
Absolutely. I am Kevin Gray. I’m the President and Chief Content Officer of Westchester Education Services. We are what I like to think of as a product development company. Publishers in ed tech companies come to us and we help them build out their product. A good example of something we might do is, a company might have an opportunity in Georgia that their sales staff is really excited about, but they don’t have the internal editorial, or design, or production support to take that work on. They might outsource to us. We would get the specs from them. We would work in collaboration with them, but we would be doing the writing, and the editing, and the page layout, really building their product for them under their oversight, and then turning it back to them.
In my role, I was employee number one of this division. We started this division about almost six years ago. In my role now, I set the strategic vision for the organization looking at what markets can we work with, what customers are we not working with that we would like to be, what kind of products could we be developing, and then also watching the general growth of our internal team, making sure we’ve got the… I have an operations director who reports to me, and I work mentoring him and working with him, and managing him in “Do we have the right folks to be able to respond to the needs we’re seeing?”
Mine’s a bit of a bridge. I see out here in this space the market’s asking for something. Okay, then I turn to Dave, our operations director, and say, “Hey, we have some opportunities here. How can we build out some support for that?”
Daphne:
Yeah, and so you’re in charge of just basically figuring out what types of full-time positions there are, who are going to be the best fits for those, what types of freelance positions, part-time positions. That’s where we’ve really connected and synced up with members from your direct hiring team to talk about who’s going to be the best fits for the roles.
Kevin shares why former teachers make great curriculum writers and editors
Often, I have heard you say, which is why I’m having you on this call right now is, that former teachers make great fits for many of the positions that you hire for, even though there are people in the editing space with three years maybe working as a newspaper editor that are probably applying to the roles as well. Why do you think teachers make such a great fit for these types of positions?
Kevin:
The biggest part is an understanding of pedagogy and curriculum. Obviously, to be a writer or editor you need to know how to write, but teachers bring a subject matter expertise that someone coming from the outside world doesn’t necessarily have. Teachers are also great because they’re really well organized often, they’re really up on the various different trends. So right now, science and reading is a really big deal, and so teachers who have already made that transition in the classroom may understand it better than our clients do. Really, that understanding of curriculum and pedagogy, and then also how to support teachers, how to build materials out that are going to engage students and that are going to support the teachers, and that are things that teachers are going to actually use. All of that is a very precious mindset and precious resource that we really like to tap into.
Daphne:
I love having those behind the scenes conversations with people talking about what is a non-negotiable, like what it is they absolutely have to have experience doing X, Y, and Z. Most of the time, it is something that teachers are able to do, but maybe they needed to work on the editing team for the newspaper, or have a little bit more experience that they put on their resume to stand out for those particular roles that we were looking to help you fill. For this conversation, we’re just going to stick to the freelancing positions that you have.
You have about four different categories of freelancing positions that you hire for on more of a mass scale. Do you mind sharing a little bit more about what those freelancing positions are?
Kevin:
Sure thing. The real bread and butter on the freelance team is particularly the teacher lens in four areas. The first is in writing, and so writing teacher’s edition, student edition in all of the various different subject areas, particularly math, science and literacy, and social studies. Those are the really big ones right now. Also, editing roles. The folks who would come in and look at the material that’s been written, and then make sure that it conforms to the client’s not just their style guides but also their conceptual guidelines. Then, really looking at also translation. We do a lot of translation work, so former educators who are bilingual, who can oversee translations and do editing of translations are invaluable in particular because education has such a specific vocabulary. You can’t just turn it over to Google Translate, or turn it over to one of these massive translation groups.
Folks who understand education and the language and vocabulary that they’re translating into are critical. Then most recently the group that we’ve added, and this is about two or three years ago, we started a culturally responsive education review service, which is a really long way of saying that we help our clients make sure that the materials they’re producing are culturally responsive, they are not just free of bias but also reaching students in ways that map to the student’s own lives or own experiences, or that others can learn through those experiences. We have a freelance position called the CRE Reviewer, where the team works with a rubric and they’re paired with other reviewers with different lenses looking at customer material, and then providing feedback on where things are not as culturally responsive as they could be, and then how the customer could edit it to make it so.
Daphne:
There are so many teachers who are really passionate about it, especially that last section that you talked about.
Kevin explains that curriculum writing contract positions are a great stepping stone as teachers transition out of the classroom
This would be probably a good fit for someone who still wants to keep their finger on the pulse and be able to support equity and education, and doing work that is intrinsically motivating, but from outside of the classroom, right?
Kevin:
Yep. It’s also a really nice entry point into the world of educational development or content development because what a teacher who works as a reviewer is bringing, is their lens. We teach them the rubric. We teach them how to look at the materials. But by and large, their student materials is they’ve probably already seen similar instances of it in their own classroom, their teacher materials that they’ve probably used before, or similar to. This is a nice way to bring folks in where they bring what they know, and then we have them looking at materials in a slightly different way than they would in the classroom. They get really almost osmosis. You sort of learn by osmosis how these things are put together in a relatively low risk way in terms of getting into the industry.
Daphne:
Let’s talk about that a little bit because that’s such an important part of this is, I’ve always told people that you want to try to get your hands dirty. You may think that you love curriculum writing, but you might not want to make that your full-time role until you sit down and you actually do 40 hours of curriculum writing as a side hustle, or for a part-time position because you may realize, “Actually, I don’t love staring at a computer all day.” I started to get overwhelmed with it. You may realize that what you really liked was the project management, or the planning part of curriculum. This is a really good, like you said, low risk way to feel out if you really are excited about editing or curriculum writing and be able to put on your resume that you worked for a company outside of the classroom as well.
Where do you see this being a benefit? What types of people have you seen go into this with the wrong expectations of what freelancing is, that we want to alleviate those roadblocks or… I’m having a hard time explaining it, but hopefully you get what I’m saying?
Kevin:
Yeah, no absolutely. I would say one of the challenges is, where it’s been a bit of a challenging fit, is that we work with a lot of different clients in the space who have their own voices and their own pedagogical approach, or their own idea about how curriculum should be created. Folks who have a broad understanding of different ways to create content and can hear what the client’s asking for, and replicate that to help the client achieve their goals, they’re going to be the most successful. Folks who have a very rigid idea of “This is the only way that math should be taught,” it may be challenging to find projects and absolute best fit with that particular background.
Daphne:
That’s such a challenging piece. That’s almost similar to a marketing position, because the marketing person’s role, they are going to come with a little bit of flair, some subject matter knowledge about what they’re doing. Ultimately, their role is to execute on what their client’s vision is. Their role is to replicate what the client’s voice is. In this particular situation, you’re going to be saying, “This is the type of math you’re going to be teaching,” but you’re going to be actually doing it and replicating what the client is looking for in that work. You may not have as much creative freedom as you would on your let’s say Teachers Pay Teachers store.
Kevin:
That’s absolutely right. Actually, it’s a challenge we see from people who come from the publishers or ed tech companies to work with a vendor as well. It’s just that we work on so many different projects. We believe in the projects we’re working on. We don’t take work we wouldn’t stand by. We recognize there are differences in the way things can be approached. And so, even folks who worked at a publisher who were used to the one way that publisher did the work, can find it a little challenging to make that jump over.
Kevin shares what former teachers can expect to make in a contracted curriculum writer role
Daphne:
Do you mind sharing what a regular hourly rate for one of these positions would be?
Kevin:
Yeah, not at all. We pay by piece. Generally, that’s by… What we’ll do is look at a page. If it was a writing position for instance, we might look at a page and say, “Okay, how much time does this take?” If it takes an hour, we have an hourly rate. Writers, we try to benchmark between $50 and $60 an hour. Editors, try to benchmark it between $30-35 an hour. That seems to be the prevailing market rate. If you had a page that we were expecting it was going to take about an hour, it’d be about $50 per page. If you were going to edit it, it’d probably be $15-$17.50 or so. It depends on the project. We do work with our freelancers to make sure that they’re compensated fairly.
The best advice that I could give is we have some freelancers who can look at those projects and say, “What’s the most efficient way that I can really create some great product here?” The ones who do that are the ones who usually end up beating the estimates, and then are highly compensated because if we thought you were going to take an hour and we’re paying for you an hour’s worth of work, and you get it done in 25 minutes and it’s still really good quality, it’s the same as if it took you an hour and a half to do it.
Daphne:
Yeah, absolutely. That’s kind of overall some of the freelancing best practices, is figuring out your systems, making sure that you create some sort of project planning and project management system. Maybe it’s potentially batch working, if you have a lot of work that you’re doing. It’s easier to let me research these 10 different topics offhand, and then let me write the copy on all 10 of them using the same type of template. But that might be something that is a little overwhelming for someone whose just coming from the classroom and wanting to dip their toes in. How much onboarding do you actually do on your end? How much training do you do for these types of roles? Are they expected to figure out how to be the best curriculum writer, or do you have resources that help kind of scaffold them into these positions?
Kevin:
We have a resource manager who does all of the sourcing and advocacy for our freelancers. If someone’s coming into a space and they are maybe looking for a side hustle while they’re in the classroom, and they’ve never done content development before, we’ll look for projects that are relatively low ask or low cognitive load, I guess. That’s where some of the CRE reviewing can be good because it’s okay look at this, and then you provide feedback on it. Some of that work has an emotional toll, because looking at stuff that is problematic after a while can be a little disheartening, but you’re actually part of making it better which I think is what drives a lot of our folks.
We don’t have a formalized training in place yet. We have been working on different ways to build out that training, but what has been successful in the past is really a scaffolded approach. I’ve got three or four of our best freelancers are folks who came to me who maybe were in academia and did some copy editing, and we found some projects where it was the kind of work that we might put an editorial assistant in house on. So, really finite set of tasks, really well-defined, perhaps a little repetitive, but it’s something that someone can get an easy win on. When they do that well, we’ll look for a more difficult project or a more difficult project.
It would be very unlikely we would take someone from the classroom who has never written anything before, never done any curriculum development and said, “Hey congratulations, you’re writing three chapters of this science student edition.” I think that would be very overwhelming. I wouldn’t want to put someone in that position.
Kevin talks about what curriculum writing experience looks like
Daphne:
Someone may be listening to this podcast episode right now and being like, “What do you mean they’ve never written curriculum? All teachers have written curriculum,” but that’s honestly not the case. There are some schools where they just, “Here is all of the curriculum,” and you are forced to basically use exactly what is inside of these books. Then there are some teachers who are given nothing and they are given the instructions for the next two weeks figure how you’re going to teach on these 10 subjects, and you may need to put something together. That’s going to vary from district to district on whether or not they have that experience. Are you looking for anything on resumes to help you decide whose gotten more experience than others?
Kevin:
Yeah, that is a great question. That’s something I think that some teachers don’t do enough of, is calling out that related skill or relevant skill. So, skill transfer. Maybe you haven’t written for a teacher’s edition, but you were part of the team that revamped the curriculum for your ELA program. Or maybe you are in a district… I spent a few years in the classroom myself and I had some objectives at the end of the year we had to get to, and then everything else was up to me. That was a little overwhelming, but it also really honed my curriculum development skills.
So, I would tell teachers when you’re looking to move into this world, if you haven’t done a lot of outside freelance work but you’ve done a lot of that curriculum development within your district, please highlight that. Show what that looks like. Explain what you did. Because that may help us pair you better with a program somewhere where we know, okay the idea of a scope and sequence for instance is probably not lost on this person. The way publishers might organize content is maybe not that different from the way you’ve organized the curriculum in your district. So yes, absolutely. I don’t think we don’t see enough of folks highlighting that. I’d love to see more.
Daphne:
Yeah, and that’s obviously something that I go deeper into in the Teacher Career Coach course of how to make sure you’re looking at the job description and pulling your relative experience into it. For these editing and curriculum roles, I feel like people make the inference that just a teacher resume is enough. I was a teacher, and they’re going to understand how this is relevant to this position. Maybe they’ve made a couple of tweaks to the language on it where it sounds a little bit more corporate, but they don’t realize these are going to be competitive roles as well. Especially the full-time ones, but even the freelance and part-time ones. It’s important that you’re demonstrating to the person that you’re applying to that you’re actually passionate about this role and that you’ve done enough research to understand how your skills translate. Just those tiny tweaks to your resume are going to demonstrate with a little bit more confidence “I know what this role means, and this how my skills will translate to it.”
Kevin:
Absolutely. That’s exactly what we look for when we get positions. If we get 50 resumes and 40 of them are “Why I was a teacher in a classroom,” and 10 of them are “I was a teacher in a classroom and as part of that I was part of a team that over the summer did curriculum review that I was in an unstructured classroom where maybe I and another teacher worked together to development the curriculum for the 3rd grade.” Those are things that are going to set apart from just a “I was a teacher in a classroom.” Yes, we can infer that probably there’s some experience there, but really calling out the curriculum piece.
And then, any writing experience too, even if it’s not curriculum writing. If you worked written articles for a local newspaper, or have a blog, something that shows that you know how to develop content. Because again, that’s a very transferrable skill, even if it’s not for the particular subject that we need. If you have the subject matter expertise and you can show you’re a solid writer or a solid editor, really show that so we can make the leap and say, “Oh yes, here are transferrable skills that we really want to bring in.”
Daphne:
I feel like this part is getting lost in translation somewhere. I feel like there’s this really big movement of people telling others to get on LinkedIn and share their day to day because that’s sharing their writing. Oh, they’re going to see that you write every single day, and you’ll become a better writer if you’re sharing what your day to day job looks like. It’s going to be far more effective if you put together a blog about gardening, and you deep dives into best practices when it comes to vegetable gardening, or something where they can see really well researched, really strong content, and not so much about just writing for the sake of writing, but writing with an actual purpose and an objective with editing and all of the best practices built into it.
Kevin:
Yep, I completely agree.
Daphne:
Yeah, I feel like that’s a part that I think I’ve told people to maybe just do one or two really great articles. It doesn’t have to be about your teacher transition or what’s going on. Just something that you’re really passionate about so that they can see it, especially if you’re looking to get into the the writing world. All the things that we’ve talked about so far could translate into full-time positions as well, how to translate your resume, how to stand out for these types of positions. The ones that you are mostly hiring for right now are freelancing positions, and that comes with a couple of nuances that I feel like it’s really important to address.
Kevin discusses what it takes to be a freelance curriculum writer
So, we talked about what the regular hourly rate would be for these types of positions. Now, how common is it for people to take freelancing positions just at your company and that’s their full-time position?
Kevin:
I would say as a freelancer I would highly encourage even the best folks that are working for us diversify and have multiple clients. But frankly, because as a freelancer, it’s expected that you’re working with multiple folks. We certainly don’t want to impinge upon anyone’s ability to work with any other providers. This world can be… It’s project by project. There might be a project that you thought was going to start in September and it doesn’t start until October. So, if you’ve got a handful of projects that you’re working on, you can mitigate the risk.
A challenge there is also to be able to understand though your limits. You don’t want to take on five projects that are each full-time because you’re thinking, “Oh, the schedule’s going to shift and I’ll make it work.” I’ve seen folks really burn out that way because they didn’t understand how to mitigate their own workload. It can be a little feast or famine, but the folks that we go back to time and time again are the ones who committed to work, got the work in on time, and then consistently deliver. If you’re taking on three projects and trying to juggle too much, that may jeopardize that and you may end up hurting the relationship with us or another vendor or publisher because you weren’t able to deliver to what you said you would be able to.
Daphne:
It’s so overwhelming. It feels like it’s a risk. It’s not going to be a full-time position. It’s not going to pay the salaries. I have these exact same concerns. When I left the classroom, I had a freelancing contract position. It was a little bit of a unicorn job. It was at Microsoft. It was a full-time contract position, so I had an annual “This is your salary for the year, but you’re at will. In three months we may say sorry you don’t have a job anymore. This freelancing position is cut off,” but it was renewed year after year after year. This is not one of those types of positions. This is a very per project. They’re going to say, “Here’s what you have. This is how many hours it is,” and it’s not necessarily going to replace your income by next month.
There is a podcast episode that I do with Jay Clouse who is hands down one of my favorite people to talk to about freelancing, because he’s so knowledgeable about how to mitigate the risk, how to make sure financially it makes sense, how to set up business entities if you need to, and all of the nitty gritty of how to find different clients outside of Westchester Education Services. If you’re looking to make this a full-time thing, people absolutely do, but that’s going to take work in itself. So, if you’re interested in learning all of those pieces, I highly recommend you to back to episode 13 of this podcast with Jay Clouse just to do a one to one of everything freelancing. There’s a lot of pros that come with this. It’s low risk. You’re putting something on your resume, and you’re getting your feet wet. You’re understanding a little bit more about this role.
So, if you do have additional bandwidth, or if you’re looking to make extra money, this is a really good fit. Is there anything else that we haven’t really covered that you feel like is really important to talk about for these types of positions, Kevin?
Kevin:
Yeah, I would say if you’re looking to transition from the classroom, pick up some freelance work while you’re in the classroom still. It can be a little bit to juggle, but find something small that you think you can do successfully so you can really get a feel for it and find out, “Do I really like doing this?” Writing every day sounds great until you actually have to stare at a blank cursor every day. You may not like that. Or you may say, “Oh, I’m really passionate about math,” but you may not like to try to deal with the six different ways six different companies want to do it. When we’re looking for folks we can bring onboard, having taken some small projects and then continuing to take larger projects is really good. The other thing that I would say is build a strong relationship with the folks that you’re freelancing with. There’s a lot of movement within companies, within vendors like myself, and within publishers and ed tech.
So, people who I met years ago in my first role are now working for me in this company. I have had the same situation where I met somebody and then years later was working with them. There’s a lot of travel within organizations. Not necessarily physical travel, but folks move around a lot. So, make friends, get to know the folks you’re working with. I will say, honestly the best way to do this is, and I would tell my freelancers this all time, don’t let… and this is cliché, but don’t let the perfect be the enemy of the good. I will take good content from a freelancer that’s delivered on time every day over spectacular content that is two weeks late and I didn’t know it was coming in. By that point, that content’s useless. Get me something that’s good. Get me something that’s on time. I’ve got editors who can work with it. Be open to feedback so you can clean it up if need be. But really, communicate with your leads, strive to hit the goals, and just turn things in on time.
Daphne:
Yeah, the networking piece of this is huge because that’s ultimately once I left the classroom and I was working in that first position, I realized very quickly it had exposed me to so many people that did go on to different tech companies. Working for a Fortune 500 company comes with a lot of perks of I knew that I would get my foot in the door at different companies, and it did. I was able to get an instructional design position with zero experience ahead of time, just someone able to vouch “She’s a quick learner and she loves video editing, and creating things on her own. She’s going to crush it in this role.” And so, I went to another startup and I was able to do that position just because someone was able to vouch for my work ethic. This piece of getting your foot in the door for people who can open doors for you outside is huge. It’s bigger than asking and begging strangers on LinkedIn who don’t actually get to see what you work like to take a chance on you because that is a bigger risk on them.
I also want to talk a tiny bit before we go about one piece of this that I know is a hesitation for someone, is like I don’t want to put together a project to apply for a position. My personal feelings about this, when there’s in the application process it’s like “Pretend you’re a project manager or put something together, or do a training for us,” if you see that project right off the bat and your gut is screaming “I don’t want to waste my time on this,” that might be a sign that you haven’t even figured out if you like this role. That is my gut, is like if you don’t want to do 30 minutes of it, but then there’s also a dark side, a more nefarious side, where companies do take advantage of people and ask them to do unpaid labor.
Kevin shares how to weigh if a potential curriculum writing client is worth your time
I know you and I have had a conversation about this as well. What [are] your feelings? Are you going to ask them to create 10 pieces of free content even to just get in your candidate pool?
Kevin:
No. What we look for, we do have some level of vetting. If you’re a writer and you have a portfolio, we’ll look at the portfolio and see if that’s a good fit. But remember, we don’t know anything about you. And so, there are sometimes some skillsets we’ll have folks do. I did it to land my first job. I had four pages of educational material I had to copy edit, and I went to the library and got the Chicago manual style, and brushed up, and worked through it. It was a reasonable ask. It was an hour of my time to prove that I can do the work. I also applied for a company once years ago that had me edit an entire chapter of a book, and then I found out my friend edited the next chapter, somebody else I knew edited the next chapter. And we didn’t get paid for it. That’s how they were getting their editing done. Don’t take that stuff on.
I’d say it’s a reasonable ask, 30-45 minutes if you’re interested in the job. Consider that you’d spend that much time in an interview, and that helps us get to know who you are. If it’s beyond that, it’s probably too good to be true and it may not be a good fit for you.
Daphne:
Yeah, it’s just such a tricky part because people get so discouraged where they’re like, “Oh, this place had hundreds of applicants,” and I need to tell them not everyone actually went to step number five. Not everybody actually saw that it took 30 minutes. They’re like, “Eh, nevermind. I just wanted to spray and pray, and just hope that my resume got to the top of it. I’m not interested in learning how to do this project because it could be potentially a waste of time.” If you’re interested in curriculum writing and editing, you’re going to want to get your hands dirty. This is a good way to at least challenge yourself if it is a reasonable ask, but also at the same time look from the lens of are they taking advantage of me? Are they asking me to put together a 10-hour campaign for them of some sort that is obviously that they could get paid for?
Kevin:
Yeah, exactly. I think there are ways you can tell when it’s the same test over and over again as well. It was clear when 25 years ago when I did that copy editing test, it was clear to me that this was a generic test. A little bit of science, a little bit of math. It wasn’t a product that was in production. And so, I could look at it and say, “Okay, that seems very reasonable. They need to see my skillset. I need to see if I’m a good fit. Sure, I’m happy to do that.” But like you said, if you’re finding yourself building a product for them and it’s more than an hour, eh. It’s either taking you longer than what they envisioned it probably should, so it might not be a good fit for you just because that might not be the right skillset, or there’s something shady and nefarious going on.
Kevin explains where to find Westchester’s curriculum writing contract positions
Daphne:
Okay, and then I have to end it with asking the biggest question, because people who are listening this whole are probably like, “Where are these roles posted?” If they’re excited about applying, where can they find this on your website?
Kevin:
We have a careers page on our website that has all the various different freelance positions that we’re looking for. So, start there. After you post, you’ll likely hear from our resources manager who will ask you to set up a profile in our vendor management tool. That helps us to pair people with the right skills. It gives applicants an opportunity to fill out, “Hey, here’s who I am. These are the things I like to do,” so that we’re able to match. So yes, look at our website and those things are generally posted there as we need them.
Daphne:
Okay, awesome. Thank you so much, Kevin, for being here today. This has been such a great conversation. It’s always a pleasure to connect with you. So, I just really appreciate you taking the time to do this.
Kevin:
Yeah, absolutely. I love doing this. I love helping more people get into the space. I got a lot of lucky breaks when I was starting off, and I’m happy to pay it forward. So, thanks for having me.
Mentioned in the episode:
- 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
