From Third-Grade Teacher and Middle-School Principal To Efficient COO

Speaker 1: Welcome to the Process Breakdown Podcast, where we talk about streamlining and scaling operations of your company, getting rid of bottlenecks, and giving your employees all the information they need to be successful at their jobs. Now, let’s get started with the show.

Dr. Jeremy Weisz: Dr. Jeremy Weisz here, host of the Process Breakdown Podcast, where we talk about streamlining and scaling operations of your company, getting rid of bottlenecks, and giving your staff everything they need to be successful at their job. Keith, I like to mention past guests. I’m going to introduce Keith Westman of Otus in a second, but past guests, people could check out, we had David Allen of Getting Things Done. Michael Gerber of the E-Myth. I always mention those ones. [Dee Clevitt 00:00:52] talked about processes and systems, and there’s so many more. So check out the podcast.

Dr. Jeremy Weisz: And this episode is brought to you by SweetProcess. If you’ve had team members ask you the same questions over and over, there is a better way. There is a solution. SweetProcess is actually a software that makes it drop dead easy to train and onboard new staff and save time with existing staff. And Keith, I was talking to one of the owners, Owen, not only do universities, banks, hospitals, and software companies use them, but first responder government agencies use them in life or death situations. We actually had them on the podcast because I was fascinating to see what are these life and death situations, but they walked me through how it has helped them. So you can use SweetProcess to document all the repetitive tasks that eat up your time, your team’s time. So you can grow the company and focus on that. And there’s a free 14 day trial, which is no credit cards required. Go to sweetprocess.com. It’s sweet like candy, S-W-E-E-T, process.com.

Dr. Jeremy Weisz: I am excited to have today’s guest, Keith Westman. He’s a COO of Otus. Otus is actually a Chicago based ed tech company that replaces dozens of tools that schools use each day with a single set system. Just one system. These days, Keith, anything that creates simplicity is a must. Okay. We have too much chaos, too much complication. We need simplicity. So this actually is one single system. He spent half of his professional life as a K-12 teacher and administrator, and has spent an equal time working in ed tech. We actually are practically neighbors in Highland Park. It’s a small world, Keith. Thanks for joining me.

Keith Westman: Yeah, really nice to meet you. Thanks for having me. And it is always a small world.

Dr. Jeremy Weisz: I want to talk about your experience as a third grade teacher and middle school principal, and how that led you to COO. But first just tell people, give people a little overview of Otus.

Keith Westman: So the problem that we’re trying to solve at Otus, and this is something that the spotlight was certainly shone during remote learning is that teachers and students are using a dozen or more different ed tech tools in order to do their jobs. They use one thing to grade, another thing to take attendance, something else to track behavior, another tool to, I don’t know, send messages to parents. So there’s all these things that they’re using, and it causes a lot of chaos for everyone. So what we’re trying to do at Otus is how can we replicate what all of those different systems do, and just have it happen in one place. And the beauty of that is people are more efficient, but the other thing is you have access now to real time data into what’s happening in your schools without having to worry about connecting all of these systems. So interestingly though, as I was sharing before we started, Otus was born at a middle school, not too far from where Jeremy and I are sitting. So homegrown in good old HP.

Dr. Jeremy Weisz: It kind of goes into probably some of the things you experience as a third grade teacher and principal. But what was it, that initial inkling, why did they create it in the classroom to begin with? What were the early on pain points that they were solving for?

Keith Westman: So they were awarded a grant by the District 112 Ed Foundation. This was back in 2012 or something. Where that grant was going to pay for each student in their class to get their device. Now, kids have devices given to them by school districts now pretty routinely, but back then it was novel. And so when they got these devices for each one of their kids, they assumed that kids were going to be super engaged in learning, they were going to be more efficient as teachers, parents were going to have these wonderful insights into what was happening. And what they realized is half the class was literally spent logging into different things. Nothing was interconnected. The data gathered from all of these different platforms they were using never came together. So it was really impossible to see kids as holistic people. And so it was like, let’s solve this problem. So similar to how the medical industry has a health medical record, a digital medical record, there really is nothing like that in education. And so that’s what we’re trying to do.

Dr. Jeremy Weisz: So there’s a lot of COOs that listen and they love hearing about what other COOS are doing. What were some of the experiences, think back, we could maybe separate out third grade teacher, middle school principal, because I’m sure those are very different things that you were doing-

Keith Westman: Very different.

Dr. Jeremy Weisz: What about the third grade teacher part do you think helps you as a COO, or taught you about being a better COO?

Keith Westman: I think the most important thing that it taught me is that other people do not share my personal background and experiences, and opinions and beliefs, and ways of doing things.

Dr. Jeremy Weisz: What do you mean by that?

Keith Westman: Well, here’s what I mean by that. Yeah. When you’re a classroom, I’m a Caucasian male, I only speak English. All right? Here I am a third grade teacher where most of the students don’t look like me. And actually most students don’t look like one another. Just a very diverse student population. We were doing a lesson in math, and some story problem. But I use the analogy of building an ice cream sundae. Okay. Because to me, everyone knows what an ice cream sundae is. Everyone’s gone through the process of building one.

Keith Westman: And so as I’m talking, I see that the interest and engagement in my kids’ faces is slowly leaving their body. And I asked them, I said, "How many in here have built an ice cream sundae?" Zero hands went up. And as a young guy, that was my first time that I realized the life experience that these people are coming to me with each day is not the same as mine. And oh, I didn’t realize that. I thought that people just lived like I do. So I think that perspective taking, the ability to be empathetic, and truly kind of meet people where they’re at is one of the most important early on lessons I learned as a third grade teacher that are applicable to life as a COO. And I guess the other obvious thing is just multitasking and doing a million things at once. All of which are important and trying to prioritize. Certainly you learn that as a teacher.

Dr. Jeremy Weisz: What was the toughest part about teaching third grade? Because you say you’re managing a bunch of things, which is similar to a COO. You are-

Keith Westman: Yeah. So I didn’t think it was tough because I enjoyed it. So I just did it because it was just part of the job. I think that one of the biggest challenges is, what’s interesting for teachers is teachers have periods of the day when they have students in front of them, right? I mean, they’re doing the things that we think teachers do, which is teach kids. But little do people realize that there’s a to-do list of 15 things that have to get done by teachers every single day. And you have to get that list done when kids go to lunch, before school, after school, when kids are at music class. Well, oftentimes things get added to that to-do list and you have to get that stuff done.

Keith Westman: So getting kind of the operations of being a teacher done. Finding time to do that when your primary job of teaching kids also has to get done is a challenge. So when you hear a teacher saying they’re overwhelmed and we have a lot of things, it’s because they are. They have their job to do and be prepared for. And then they have all the tasks to do. And they’re not really given much time to get those tasks done. So that’s where things start blowing beyond the the traditional school day.

Dr. Jeremy Weisz: Yeah. I feel like, Keith, you have a book. There’s a book All I Need to Know I Learned in Kindergarten. Yours should be like the Ice Cream Effect and how no one’s different. I don’t know. Something like that.

Keith Westman: Maybe you could be a ghost writer.

Dr. Jeremy Weisz: But I’m interested. So we talked about the ice cream sundae. I love that story. What was something as a COO that you went into explaining something or doing something, and you had to change how you did things because you saw people had different perspectives? Maybe it was you were implementing, maybe it was onboarding. What was-

Keith Westman: Yeah. The best example is just scaling a business. Otus is the second ed tech company that I’ve worked at. The one before, we were small team, and then it grew over the years, then we sold it. But I face this every time we’re scaling a department or a team or whatever. As an early employee, as a COO of a company with six people, and you’re just the COO because why not, you have a lot of responsive abilities. As you scale, as you bring in a sales team, as you bring in a marketing team, as you bring in a finance team, the things that you used to do, you no longer should be owning so that you can have the people who are hired to do it, need to do it.

Keith Westman: So one of the lessons I learn every day, literally every day, is just because I think we should be doing a marketing campaign to this type of user, and do it in this type of way, and it should start in two days, doesn’t mean that that’s what the team thinks is best based on their data. So for me, the ability to slow down and listen to other perspectives, and have my mind changed based on their view of the situation is very similar to me reading the room of third graders who are not on my same page and having my mind changed saying I got to do something differently in order to keep going in the right direction. So those are examples. And those happen, again, every day where it’s like I just say, hey, let’s do this because of whatever. And I’ve really had to make a concerted effort to just listen and stop talking. My wife’s grandpa gave me probably the best piece of advice I’ve ever heard. And it was never miss an opportunity to keep your mouth shut.

Dr. Jeremy Weisz: I like that one.

Keith Westman: He’s a Harvard law grad. And that’s what he shared. But again, it’s all the idea of listening and perspective taking, I think.

Dr. Jeremy Weisz: I love it. Tell me about how you navigate that as a leader. So let’s say this marketing campaign, you’re like, we need to launch this in two days. The data from the marketing team says something different. Walk me through, do you have an all hands meeting? How do you navigate that?

Keith Westman: So, yep. Great. So what I would do is I would pull a team together and I would say, "I’m not going to focus on the what we need to do. Let me focus on why we need to do this. So here’s why. What we know is that a law changed in Idaho. They’ve passed a bill that will literally fund the purchase of a software like Otus. So if we can make that known and get Otus top of mind to people in Idaho, that’s a good thing for us." If I can tell them what has happened, that is the why we need to do this. And then if I can say, now you do the what. You worry about if it’s Twitter, Facebook, email, cold calls, I don’t care. That’s what I’ll try to do. That’s what I hope to do. So if I can focus on the why, and let the team be responsible for the what, that’s what I did in this case.

Dr. Jeremy Weisz: I love that.

Keith Westman: I don’t need to come at you with the what to do. Let me tell you why we need to do it. And you figure out the what.

Dr. Jeremy Weisz: Yeah. You focus on the why. And then when you’re focusing on the why you are demonstrating why there’s an urgency and why we need to do it in two days. And they may go, "Well, we can get the emails done in two days, but if we’re going to do this direct mail campaign, that’s going to take three weeks." You’re like, "Cool. Release the email." So they’ll figure out the what, and basically come up with the solutions. But you’re them kind of the backgrounds that they know why this is of urgency.

Keith Westman: Yeah. And the autonomy to make their own decisions. And that’s what really everyone wants. Everyone wants to control their own destiny at work and in life, but especially at work. And that’s one way to do it.

Dr. Jeremy Weisz: So I want to go back to the evolution of the COO, which is when you were at the company and you scaled up because there are maybe people listening right now like, that sounds amazing, Keith, I want to scale up my company. So I’m wondering your role as a COO, let’s go back to that six person company, what are some of the team members or departments that you started to bring on to remove yourself from different functions at that point?

Keith Westman: When I first got to Otus, small team, one of the co-founders and me, so he was still working full time as a teacher. So I was doing the prospecting of sales, doing sales demos, closing sales. And when we’d make those sales, onboarding new clients, supporting new clients, sending out invoices, just doing all of the business operations type stuff. Not any the development. So as we started growing, we started just slowly transitioning one of those responsibilities to another person. So now we have someone that’s going to do the training and that ongoing support. And then as we grew, then now that person’s going to have more people that are going to do the training.

Dr. Jeremy Weisz: What was the order, Keith? I’m wondering because you are very systems oriented. So I’m wondering what you decided to choose to get off your plate first in what order.

Keith Westman: First was client services. Onboarding and training of clients. Second was sales. Third was marketing. And then finally was finance operation, just the accounting and finance of the company.

Dr. Jeremy Weisz: Because I imagine you were feeling that you were doing whatever you felt was the most important thing at that moment to do, and handing out the other things that, okay, I should be focusing on, okay, I get off the training, but three things are the most important. Then these two things, and these one things. So now what to you is the most important function for you now that you have these people and systems in place?

Keith Westman: Yeah, that’s a great question. So now I pretty much live and die by the data that those teams generate. So looking at our satisfaction ratings and client services, looking at our sales pipeline, looking at how frequently we’re contacting existing clients, looking at how our marketing campaigns are doing. So that based on what the data says, I can turn my attention towards where I think I can be helpful. So hey, this looks like it’s working. How do we do more of this? This looks like it’s not working. How do we stop doing more of that? So for me, that’s really where I try to spend my time.

Dr. Jeremy Weisz: Yeah, I get it. You go in there and whatever needs attention, whatever needs troubleshooting, you go in and you help. I’m wondering what’s the meeting frequency look like. Because I’m imagining there’s a lot of data, especially with the business you have, and you probably have to consume a lot of data to make decisions. What is the meeting frequency with the leadership team or other people at the company look like?

Keith Westman: We do a weekly leadership team meeting, so I oversee the business operations side of the house. And then one of the co-founders oversees the delivery team. So that’s the product development, the engineering, the UI, QA, and stuff like that. So I meet with the leadership team from my side of the house once a week. And the way we do it is just put everything that you want to say in an email. We get together at 10:00 on Tuesdays. We all read the list and then we ask questions. So we try to make it very efficient. Don’t read the email, put it in a Google doc. We’re going to read it and ask questions. We do that once a week. And then I’ll have one-on-ones with people that I manage. So the leaders of each of those teams every week. And then we just touch base throughout the week as needed.

Dr. Jeremy Weisz: I love it.

Keith Westman: I hate meeting. I should say that I hate meetings. That’s so that’s really where that comes from. I hate just sitting to meet to meet. So it’s like-

Dr. Jeremy Weisz: Right. It’s a productive meeting, it’s great.

Keith Westman: Awesome. Yep.

Dr. Jeremy Weisz: Yeah. Middle school principal. So a third grade teacher. Now you transition to middle school principal. What’s a story that sticks out? I don’t know if you can top the ice cream sundae story, honestly. That was a great story. As a middle school principle, and what you learned that you take as your role as COO.

Keith Westman: What I learned most is that even if I have the best intentions for… I have a better story for you. End of the school day, I go out, watch the kids get on the bus, the friendly waves to parents. Everyone’s good. All right. Come back to my office. And the red light on my phone is flashing. Like, boom, boom. I’m like, all right. The message. First message. "All right. Dr. Westman, If you could give me a call, I understand what you’re doing, but I have a problem with it." Okay. Next message. "Dr. Westman. I just want to say, thank you. I love what you’re doing. And if you could just keep…" Okay. So about 17 messages. Okay. And I’m like, what the hell is this even about? I don’t even know what did I do.

Keith Westman: Well, what I realized is it was anti-bullying week in the country. And what I thought was a good idea is, at lunch, I’m going to assign kids where they’re going to seat so that they can get to know other students in their grade who they may never sit with or have classes with. That was not a good idea. You have some parents who thought it was amazing. Other parents are like, "That is my kid’s time. How dare you tell my kids where they’re going to sit lunch. Who are you? Blah, blah, blah."

Keith Westman: So what I realized is that as long as there’s someone else in the room with me, there will be another adult who has a differing opinion or a different way of doing things. And what I learned about myself is when people don’t like a decision that I’ve made, that does sting. Okay. Now that sting has worn off. I mean, I’ve been in a leadership role since 2008, so whatever, it’s 13 years. So I’ve made enough decisions that people don’t like that it doesn’t sting as much anymore. But I think that’s the biggest lesson I learned is when you’re a teacher and a kid disagrees with something, it’s all right, well I’m the teacher. When I was a principal, now I have teachers, parents, you have adults who disagree. And I wasn’t used to that.

Dr. Jeremy Weisz: When you’re a principal, I mean, if there’s thousands of kids, and some are single parents, some have two parents, let’s say you have 3,000 now people that are calling you that are either going to agree or disagree. Let’s say just half of them are going to disagree. So now you have 1,500 people, and every decision they’re not going to like what you do.

Keith Westman: Now fortunately, a lot of people, not everyone calls. And I should say that I had a great experience. But you’re right. It’s like when you’re in a leadership role, there’s things you’re going to do that people like and things that people are not going to like. And that’s just what it is.

Dr. Jeremy Weisz: What was something, and I thought you were going to say, well, putting out fires. I mean, you’re getting, just kids, something happening with a kid in the classroom, out of the classroom. What’s some decision that you made that you remember, and you still think back, and this was the right decision, this is the decision that should have been made, but it was the most controversial, or caused the most stir with what you did? Maybe it was something you assigned a teacher, or hired a teacher. I don’t know.

Keith Westman: No, no, no. Fortunately I didn’t get sucked into a lot of controversial issues. But one of the things I did that I remember some people were not thrilled about. And then I was at a retirement party a couple years ago, years after I had left. And they’re like, "Oh, you know what? We’ve turned the bells back on." So what I did is I turned off the bells in the school. At the end of a period, the bell rings. I turned them off. It was like, well, how you going to know when class ends? Because you’re going to look at the clock. And you know the class ends at 11:30. Well, how are we going to know that kids are on time to class? Because you know when your class starts, and they’re going to walk in.

Keith Westman: So that one I felt was good because it allowed classes to end naturally at the natural pause. So if the teachers in the middle saying something, and you have a bell go off, you remember middle school, kids get up and they bolt. So now it’s just like, we’re people. Let’s just end the conversation, and then you go to your next class.

Dr. Jeremy Weisz: Or they start packing up because they know the bell’s going to ring.

Keith Westman: Yes. So I was trying avoid that.

Dr. Jeremy Weisz: And it’s not even at the bell. It’s before the bell.

Keith Westman: That’s what I was trying to avoid. I still think that was the right decision because the hallways were just chill. They were more chill because there wasn’t this rush.

Dr. Jeremy Weisz: And what pushback did you get from teachers and parents?

Keith Westman: Not parents. The parents are even there. So they wouldn’t know. I think certain teachers liked it. Other teachers liked that there was a structure to the day, and kind of the kids knew what to expect. But we still did it and people were cool with it. But then a couple years back, I’m at a retirement party, and they’re like, "Oh, you know we have bells again." I thought that was kind of a shot saying, hey, we didn’t want to say it to you then but-

Dr. Jeremy Weisz: We overturned you, Keith.

Keith Westman: Yeah, exactly. Yeah, yeah, yeah. Yeah. So who knows if that’s majorly controversial.

Dr. Jeremy Weisz: That’s funny. What about either at the past company or this company that you made decision that, same thing, like turn all the bells off, that maybe got some buzz or stirring and take some time getting used to?

Keith Westman: At my last company, changing commission structures with sales people. That is always going to be the worst few days of work. Well, hey, I think a lot of companies are facing right now big things that could ultimately become issues. Which is once the world opens back up, do we go back to work? What’s that going to look like? So we had our office in the Google building in the West Loop. We had a four year lease. It ended August of 2020. So after COVID, we just let it expire. And we’re like, let’s see how things shake out afterwards. And now we’re at the point in time, Chicago’s opening back up. Now we have a lot of remote employees, but what do we want to do? Are we going to get an office? Are people going to have to come back to work?

Keith Westman: As a company, what we have decided to do is we’re going to get an office space. We don’t need an office big enough for everyone, but it’ll be kind of like a coffee shop. Come in. It’s a place where you can come in and work if you want to be around people. We’ll have open seating or whatever. But we’re going to feel that out. But I could see where there’ll be some people who want people to come back every day. Other people who don’t want to come back. So I anticipate that’s the coming decisions that we’ll be going through.

Dr. Jeremy Weisz: Can you expand a little bit about the commission structure piece? How did you decide to structure the commission structure? And you don’t have to share details you’re not comfortable sharing. I’m just curious.

Keith Westman: Oh, I don’t care. Yeah, yeah. No, I don’t care. My dogs are freaking out right now because my daughter’s probably walking. Oh no, she’s not. I don’t know what that is. What we were doing is, so we were a software as a service company, and the sales people were not only making commissions on the first year of the sales, but also every renewal year, even though our client services and support team owned the relationship in those renewal years. And so we wanted to end that. So we’re going to increase commission in the first year, and then remove the commission in subsequent years. That went over like a lead balloon.

Dr. Jeremy Weisz: Yeah. Well I mean, it sounded like you kind of factored some of it in by increasing it in the first year. It just-

Keith Westman: It still wasn’t going to work out. I mean, assuming a salesperson was going to be at that company for a number of years, you start really making bank as they start adding up. But what we realized is we want to incent new sales. We want to incent a sales team on new sales. Incent client services team on retaining clients. But hey, I was a principal. I had no idea what I was doing at the time. And that’s what we did. You know what I’m saying? We did a commission structure that made sense to me as someone who had never worked at a company before.

Dr. Jeremy Weisz: There’s a lot of factors in that, Keith, but what is the range now that you’re experienced, if someone’s like I want to put a commission structure in place for sales people and for client services, is there a percentage people should be thinking about when-

Keith Westman: I don’t know. It just depends. I think it depends on the size of contracts and things like that. Our average sale is $25,000 for a school district, depending on their size. If I’m selling something where our average deal size is a half a million dollars, a 1% commission would be pretty sweet. A 1% commission on a $25,000 sale would be terrible. So I think depending on deals size. I think more what you want to look at is what is the annual on target earnings for a salesperson? Where do you want them to be for that industry? Is it 200 grand? Is it 150 grand? Is it 500 grand? And then work backwards from there.

Dr. Jeremy Weisz: Keith, for first of all, thank you. I have one last question before we end this. And I want to just point people towards Otus, it’s O-T-U-S.com. If you are a school district, or if you are a principal, if you are a superintendent, you should check out Otus. Or if you are a parent and you’re like I just want to be communicated better, then mention this to your school. Last question is favorite features. It could be an evolution of the features of Otus, but what are some of the fan favorite features and people get in, this is game changing for a school and helping that school work with the students and parents.

Keith Westman: So the ability to, at least for Otus, is there’s this thing called standards based grading. Okay? I think it’s the little bit in place in the district where our kids go to school. But the idea is that students are not given A, B, C, D, F. Instead, for math, it’s like here are the 10 things you need to know about math in this grade level. And here’s how well you’ve mastered these different concepts. A lot of times when school districts roll that out, parents don’t like it because it’s not what they had when they were in school.

Keith Westman: So for us, what’s the game changing feature, Otus has the ability for teachers who, as they’re giving their tests and assignments to their students, students do the work, Otus grades it for them, and then organizes all of the results into this interactive grade book that parents can click on and explore, and really understand how their kid is doing. So it’s like, not only do I know how they’re doing in math, but here’s the skill they’re supposed to learn. Here’s how they did last time. And here’s the question that they had to answer. So it’s just that type of stuff. For teachers, it’s the ability to say, yeah, I’m going to give a test. I don’t have to grade it, and everything’s going to be organized so I can just take action with the data. That’s game changing for them. And then for parents, just the ability to understand what this whole new way of grading means. It’s game changing for them.

Dr. Jeremy Weisz: I feel like Otus allows parents to be the COO of their kids’ education. Because it creates a granular look at what the child needs to do specifically. I don’t know if you agree that or not.

Keith Westman: That’s exactly right. It’s like a holistic view. So it’s like, what do they need to do specifically? We also know that we just don’t want our kid to be great at math, but also misbehave and disrespectful. So we can also look at their behaviors, and we can look at their strengths and their interests. Everyone says, oh, kids are more than data points. Well, kids are more than assessments data points. There are also data points about what they’re interested in, and data points about what they’re passionate about, and data points about how they like to learn. So they are more than data points. They’re humans. But we can look at a lot of different data points and really get to know someone. And that’s what we want to do at Otus.

Dr. Jeremy Weisz: Keith, I want to be the first one to thank you. Everyone check out more episodes of the podcast. Check out SweetProcess, check out otus.com. Thanks so much.

Keith Westman: Thank you, sir.

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