Product Rebels
Product Rebels
Building Product-led Teams with Conviction
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What does it take to turn a struggling edtech platform into a mission-driven product powerhouse — in under a year?
Vidya Dinamani and Heather Samarin sit down with Jared Harless, Chief Product and Technology Officer at BookNook, as he talks about his early days bootstrapping digital products inside a billion-dollar publishing company, to leading a turnaround that grew revenue 25% year over year and pulled customer retention from 27% to 70%...but the work is far from over.
Jared gets real about the kind of conviction it takes to build before you have permission — and how going straight to the market before writing a line of code is still the most powerful move a product leader can make.
Bringing your users in and the don't fall into the trap of build what they tell you to build and instead watch what they're doing, listen to what they're trying to solve for and build solutions for the problems.
SPEAKER_01Hey product rebels, welcome back. Today we're joined by Jared Hallis, a product leader who has spent his entire career in ed tech building products that shape how people learn. Jared spent 17 years at McGraw Hill Education, where he rose from marketing coordinator to VP. He led the company through a massive analog to digital transition and built products like adaptive learning platforms that reached millions of students. Now as chief product and technology officer at Booknook, he's led a strategic turnaround of the K-8 virtual tutoring platform, growing revenue 25% year over year and taking customer attention from 27 to 70% and driving the company to its first profitable quarter within a year of joining. We're so excited to dig into Jared's story and hear how he thinks about building product-led organizations in a space where the stakes are as high as they get. Kids learning to read.
SPEAKER_00And I think that translates kind of well in that, you know, this is this is in the product leadership space. I think of a product rebel more as really, really a strong belief in a position with enough conviction to fight for it. And that means moving the barriers, getting over hurdles, doing what it takes to bring something to fruition. Whether that means it's a success or not is less the point and more about taking that leap of faith to go chase what you believe is right.
SPEAKER_01Yeah, very cool. And gosh, it feels like we're living in sort of a dangerous time. So I think the start of the old description feels very apropos. Tell us an example. Go right into a place when you felt like a rebel.
SPEAKER_00Yeah, I actually it's one of perhaps my favorite career moments that I can reflect on. I've been doing doing this thing, so to speak, in ed tech for longer than I'll admit out loud unless you coaxed it out of me later. But early in the process was working with an organization that was making this massive pivot from analog into digital. And it meant that there was a lot of legacy and a lot of people who didn't really believe that you could do what you could do on paper online, which is kind of a wild concept. And this happened to be in the space of education, which makes it even wilder to reflect on. But I was working with a mentor who's still a wonderful friend of mine, and we've done some really, really, really cool things since this moment. But we came up with this wild and crazy idea that you could teach and deliver qualitative higher ed content in a virtual environment. We got scrappy, we built some proofs of concept, and we took it to the leadership of the organization that we were working at. And they sat us across the table, big mahogany rooms, of course, and looked us directly in the eyes and just said, no. And so we uh fortunately knew they were wrong. So we went and we actually scraped together and sort of bootstrapped in the context of a billion-dollar organization enough funding to go build and develop what we knew was right. And ultimately it became such a market success that the same leadership put us on top of or on the stage at a corporate headquarters and award us a corporate achievement award because we penetrated a market with such quickness and such depth that it actually unlocked the opportunity to build out an enormous amount of follow-on tech in this space, which was super cool. So, like just that again, that belief in a conviction, the staring at the opposition down in the eye and say, I'm gonna do it anyway. And it worked.
SPEAKER_02Love it. Love the daring attitude and the conviction. A lot of us get a little scared off when you have leadership that sort of pushes back. So I'd love to hear for our audience what were the three or four major strategies you took to enable you to get through that? Because I'm sure at every stage you need resourcing. You need to have this as a priority, maybe in other platforms in the organization that that were like, hey, I don't have the resources for this. This isn't a blessed program. I can't help you. Talk to us a little bit about some of the practices or the tactics you took to enable that success.
SPEAKER_00We went straight to the market. And so the only, you know, come up with a good idea, right? Have a good idea or get behind a good idea. Either way, we went straight to the market and presented the notion on scratch pads and easels and symposia and focus groups, and we brought people together from different walks of life and different parts of the space. And we iterated in real time. And we came up with all the different ways that we could deliver content in a way that hadn't been delivered before and gave them an opportunity to sit up and think outside the book, so to speak. And we built a following and we built an adoption list before we ever started coding. And so by having market-driven demand, outside in thinking, by defining product market fit before we even started to get down to the hard work, we had an ambassadorship, an engaged sort of VAT population that we could tap into at every single iterative moment throughout the development process. And so by the time that we were production and commercial ready, it was already pre-sold. And so the market was established and we didn't give ourselves an opportunity for failure. Micro failures along the way, of course, but ultimate failure wasn't an option. And so I think it's that outside in, it's that bringing your users in and the don't fall into the trap of build what they tell you to build, because otherwise, in our case, you'd end up with just a deeper pile of multiple choice questions. And instead, watch what they're doing, you know, listen to what they're trying to solve for and build solutions for the problems.
SPEAKER_01Very cool. You listed so many best practices there and things that we definitely have, you know, talked about, really built our business around as well. One of the things that you said in terms of listening, showing customers taking it to market early is that you do get a lot of feedback. And I want you to take us one step deeper into they'll probably tell you a lot of things, but people have a very specific perspective, especially coming from the education. I love when you said just build more questionnaires, build them longer. What is your process to turn that into insight? Tell us like how you listen and then how you make that decision on what's important.
SPEAKER_00Yeah, I'll be honest with the project that we've been discussing, it was just scrappy, sort of intuition, and it wasn't really built on process. And so that was part of the scalability in the long term. Like, how do you make this fabric of an organization going forward? And so I'm actually going to answer your question, but in the context of the next project that followed on. When we built this initial offering and we proved that it was there was a there there, it gave me an opportunity to springboard my career in terms of how do we then think about, okay, we we were working in these quantitative areas. Now we're tiptoeing into qualitative, but what happens if we look at the entire span of offerings? And how do we go about doing that in a scalable fashion with now thousands, millions of stakeholders? The platform ultimately, by the time I left the organization, we're talking about served six to seven million learners every year. And so that level of scale and the ability to rapidly produce that type of user volume clearly has got to be built on something better than just scrappy intuition by two guys having a good time with some undisclosed funding sources. I was actually invited to participate in a project that was to go out and build that scaled platform and figure out, okay, if we're going to do this, how do we accommodate everybody? Which is always a dangerous question to answer in product development. And I know that now, I didn't know it then. But we were, we engaged in an ethnographic research project, which was all Greek to me at the time. And eight of us flew to Manhattan on consultance hours, Sundays through Thursdays. And we sat in a small windowless room and we we designed and defined what we thought we were going to build. And then we actually did a lot of interviewing. We did a lot of direct observation of users and what their behaviors were. And then we started to build. And by build, we were building paper prototypes. If you've never done paper prototypes, and literally is what it sounds like. It's stacks of post-it notes on top of each other that you click with a Sharpie and you can track everything and you're navigating and you're starting to understand what UX concepts are. And meanwhile, this is 2005, 6 in a publishing industry, right? There was no such thing as a digital technology-driven product management organization. And so these were all brand new skills that were coming into the org. It was a blessing to be part of it. And we were traveling all over the country with these paper prototypes in briefcases, effectively. I mean, that's like walking on the airlines handcuffed to this whole pile of crazy stuff that nobody has any clue what you're about to do. And you sit down next to somebody and quite literally watch over their shoulder. And every time they do something, you claim an assumption. Don't ask them, what do you do? Instead, I see that you are doing this or I think you are doing this. And that way it gives them an opportunity to object in a much better fashion. Because if you simply ask somebody how to tie a shield to tell you, you loop and swoop and pull them tight, chase the bunny around the tree, whatever you do. But if you watch somebody half the time they drop a lace, or the knots inconsistent, and the one loop is high and one loop is low, or they're both low, like all those different variations are breakdowns. And so we were looking for ways to eliminate breakdowns based on the general outcome or job to be done that people were trying to achieve. And so it was lots and lots of hours and time. And every observation was recorded, every observation was transcribed into a post-it note. And now I know that you guys are big into affinity diagrams. And so we had a wall that was two conference rooms long, that we had entire groups of organizations walking and putting post-its and questions. And we quite literally built it by the book. And I don't think there's a better way to answer it. How we got all that insight and translated into what are product feature functionality? No, like fast forward 15 years, I don't have time to do that anymore. And so that's the rub in this space these days, especially with how quick it's moving and what the dev cycles need to be and when your the expectations are you're getting solutions feature functionality out a heck of a lot faster than 12 months down the road.
SPEAKER_02This is fantastic. We love rolling up our sleeves. I think the best product leaders we've talked to, even on this on this podcast and just worked with in the past are those that want to be at the grassroots level listening and observing and talking to customers. And so we love this. The challenge comes when you are scaling your own teams, right? So there's a point at which we have to figure out how to take what we've learned and have a passion for and scale product teams to do the same because you can't be in all places and all. Talk to us a little bit about how you took your sort of passion, curiosity processes, and practices or philosophies and how have you scaled that to build really great product organizations to do the same.
SPEAKER_00Wonderful question. And I I feel like this is one of those questions that everybody asks. And I don't know if anybody has like a real answer. I think I have a lot of words I could use to answer the question, but like some of it just has to be you, right? Like if you're if you're not by nature a leader, it's going to be very difficult to just build a team based on process. And so I like I think some of that is just naturally inherent. And I don't mean that in like a tromping my horn type way, but I love to surround myself with people who could take my job. In a 17-year career, early part of my career at a single company, I never vacated a position that wasn't refilled by somebody that I brought up and coached up into a position, which is a wonderful thing to be able to say. The in my last couple of organizations, I have brought very select people with me that are the right skill sets dependent upon the next company's strategies and needs and things like that. But once you start to get those pieces and those puzzle pieces, the ability to identify the gaps and not be afraid to hire to fill them rather than trying to, you know, to hire unicorns every single time you go around, like that's important. You get cross-functional collaborative skill sets. People can work across different parts of the organization. You can task people out with different parts and functions of the overall product org. I rarely have a single product manager that is the big air quote, the CEO of their product, right? Like they don't have a PL, it's not real. And so instead, it's more thinking about user types and persona and different aspects of things, you know, where people are coming into different parts of a collective, you know, collaborative product and solution. I do think that there is a lot of transparency and candor that has to go into being real with people. It's okay to disagree. I'm not always right, but I will try to be. And but I am at the same time, I'm absolutely willing to listen and let people prove their point if they have conviction. And so I think I I don't know if that directly answers the question. And as long as I've been trying to answer that question in my life, I don't think I can just hit it with a sentence.
SPEAKER_01Yeah, I think the fact that you've got that record of replacing just shows the kind of leadership that you're practicing. It's it's very, that's very inspiring. Um, I want to go actually back to something that you said just a few minutes ago. And you said it in passing. So I just want to go back to you'd spent all this time early on with you know, long ethnographic, various different sort of like projects that you've done for research. And then you said, gosh, do we have the time right now? And so let's can we explore that? What does it look like now? Because it it we are under pressure to build faster. There's lots of new sort of technology, but I think we're still very much in favor and we care so much about listening to customers. So I'm curious as to what you meant by that remark and how you're actually involved with customers now.
SPEAKER_00Yeah, definitely still constantly involved with customers. And I don't view customers as process, they're a constant. What I was really referencing was more the luxuries of affinity diagrams and easels and whiteboards. And I work in a fully remote environment now. And once you can correct the thought process, I think that you don't necessarily need the tools all the time, as much as I would love to employ them all the time. But if you can get people to be thinking about outcomes versus outputs, and you can get people to be thinking about assumptive conversations and giving well, they're giving clients, giving users, giving people, giving whoever you're interviewing the opportunity to tell you you're wrong and then be able to listen to that, that some of the structure goes away. Like at one point, I took a lean six sigma certification because I needed a framework. I was involved in a heavily operational project across pan organization, and like everybody was using different language, and I just needed a framework and it did a little research, and that was the obvious language and vocabulary. And if I could communicate in that model and help people kind of understand and give a little bit of places for people to go research and understand, then they could keep up. And that is sort of similar to leveraging ethnographic research studies and affinity diagrams and I love user story maps. Can I do a user story map for every feature? No. Does it need to be done for every feature? No. But when I came into the organization I'm at now, the product managers were very green and they didn't really have that same level of coaching and leadership, and they hadn't been part of those, you know, big undertaking soup to not projects. And so introduced them to user story maps. And we did it on Miro, which was a lot less fun than doing it in person. But we helped, it helped them and it helped them. Part of the project here was to convert from a sales led to a product-led organization, but it helped the org understand the trade-off and decision-making process and you know how you can slice into an MVP or a V1 and all those things. And so, in a very roundabout way, it's if we can get the thinking right, I don't think we always need to apply a tool set to every product development decision that needs to be made. And then when you throw in things like cowork and cloud code and all this V0 and lovable, I mean, it's like they've they're starting to replace some of that process so long as you don't displace the customer and the user needs.
SPEAKER_02Yeah, what a great point. And that was going to be the my follow-on question was in this age of AI, we hear so many different ways that AI is being infused into sort of the more discovery process. Vidy and I have a very specific point of view around this, but I'd love to hear your point of view on when and where is AI appropriate in this sort of I'm gonna call it the discovery process, which is amorphous and people define it in different ways. But how do you think about AI and where it should go and where we need to stay at the grassroots where we've been?
SPEAKER_00Yeah, this feels like a trap, but I will I will give you my my perspective.
SPEAKER_02It wasn't meant to be a trap, not meant to be no trap.
SPEAKER_00So I love the ability to even back to the book on user story maps. Like one of my favorite images is three people shaking hands, all in agreement, and one of them with a thought bubble of a triangle, one with a thought bubble of a circle, and one with a thought bubble of a square, right? And they're all 100% dialed in. Love it. We're ready to rock and roll, let's do this. The ability to make sure that everybody's thinking about a triangle is like it is awesome. For me to be able to, I'm not a coder, for me to be able to write a PRD with Claude and then tell Claude to make it and then take that to my team, be like, this is what I'm trying to describe. I heard this on a client call the other day. Like, let's fit, let's shop this a little bit and figure out if this is a scaled opportunity or if this is kind of a one-off and figure out if we want to apply resourcing to it. No question whatsoever as to what it is we're talking about. And the team immediately goes into edge cases, right? That's good and bad. But the rapid ability to get complete and total alignment is like something that I think product management is has been screaming for since inception, maybe. And it just cuts the timeline so dramatically. The other thing I think it's doing is allowing the engineering team to become a much bigger part of the discovery process because they can, what I've been finding is that if I can get a high-level output PRD over to an engineer that's equipped with an AI toolkit that understands the stack, they can not only prototype for validation, but they can also do it in a production-ready fashion. And we're shipping things on weekends that would have taken us months before. And so, as much as I hate the idea of replacing people with AI, I absolutely love the human in the loop, superpower people, and make sure to push on the guardrails, right? And leverage it for discovery. Should you build everything zero to want and be the first one person billion dollar organization, a lault man and all the powers that be, like that's not really what I'm chasing because I think there's a lot of there's a lot of risk and scale that approach.
SPEAKER_01I think the way that you just set this up in terms of how you presented that to your team, how you're sharing the structure and like what you expect. I heard this, I'm showing you what this looks like. And then it's really like, let's go test this, right? This isn't a go build, this is a starting point to get us very quickly on the same page. I love that framing from a leadership point of view. What else? How else are you guiding your team in terms of use of these new tools? What else are you telling them and modeling behavior on?
SPEAKER_00One thing that we have found that the company as a whole, we're a small company, but that there's not a really there's not a big operations side of the organization, especially like a tech-enabled operations side of the organization. And so I've been turning the team loose on our internal processes recently because a lot of it has to do with extracting, understanding, and translating and transforming data for either external purposes, client purposes, or even business intelligence and internal. And how can we communicate back to the organization in an effective fashion? And so we've been giving a long leash in a safe way. We use bedrock and PIIs covered and obfuscated and all those types of things. So we put policy and guardrail around it to make sure people aren't making just silly choices. But the ability to be a leader from a product perspective is so rooted in communication and the ability to communicate across the organization depends on data, in my perspective. You can have a really strong conviction, but if you can't get out and prove it somehow, then it's not really all that great. And so I've been, everybody on the team has a cloud license. Everybody is able to come to the table with a show and tell on a regular basis. We've got the Slack channels, we're showing off all the cool things that we're doing. But the risk is not getting distracted by the shiny objects, I think, because you can go so fast and because you can do anything anytime. And the worst thing that I have seen so far is somebody builds a wonderful automation and it creates this great deliverable, but the team that's supposed to then use it tries. At one time, doesn't really get it fully, didn't have all the context, doesn't you know know the narrative, and instead just defaults back to their old clumsy spreadsheets that they used to use. So I do think it is it's a blessing and a curse. You can do everything, but it can result in doing nothing if you're not careful.
SPEAKER_02Yeah, so true. And and your response on how you're using AI is fantastic. And that wasn't meaning to set you up at all. So I didn't get trapped. Yeah, no, you didn't get trapped. No, I feel like one of our biggest challenges that we see with teams is not leveraging their own critical thinking and listening skills prior to using AI, right? Oh, I'm just going to use AI to take all this and tell me what to do next. We even had one team utilize AI as a customer for a customer interview about a product. So there's a time and place when AI is fantastic and it's really as a partner to your thinking, not as a surrogate, right? So I love your response.
SPEAKER_00AI is a tool. It's not a thing. Yeah. And if you understand that it's a tool and use it as a tool for what the tool is good at, it's incredibly powerful. If not, it just puts you in a build trip. You're just building stuff that nobody wants. And so it has no value.
SPEAKER_02And faster.
SPEAKER_00Faster. And sloppier. And nobody even knows what's going on behind the scenes. Yeah.
SPEAKER_02Yeah. One of the questions we get from some of the leaders that we work with is it's really hard to understand the return on the investment we're making in some of these AI tools and sort of augmenting our processes with AI. What's your response? What's your response to that? Is that important? Is if it is, how are you doing that? And if not, what do you want to do to make that happen?
SPEAKER_00If I followed the question well, we have found very measurable value on our engineering side of the house in terms of what we can share. Now, we also are very, very cognizant on what can it do for our legacy stack versus what can it do for our net new feature functionality. We try to move to shared services. And so making sure that all those things have well-documented endpoints and all those things are wonderful, but we still risk a QA bottleneck if we're doing too much and too big and too fast. And so we've taken a very metered approach there, but I can tell you that a zero-to-one replacement of a tool that we're licensing right now cost me $700 to build over the last six days. And so I know exactly what the reward is there. That's a $60,000 offset. And so rock and roll, we're gonna we're gonna put that to production. On the more product side and business side of the house, it can be a little bit more challenging. And so as I mentioned earlier, by pointing the team with these tools to our internal operational workflows and processes, we're able to measure it in man hour offset. And it's like quite literally taking a couple hours of click, copy, paste work and turning it down into boop, right? Just boop it. And it's done and it's logged, and you can review it and you can validate it. And you know, it looks great, and it can automatically send and dump in a Salesforce and be ready for the AEs to take it, like all the things. It's fantastic, hyper-measurable. Can I say the same thing for my teams just kind of rapidly prototyping a bunch of great ideas that day? Like, probably not. I mean, I think that's probably on the negative, maybe the adverse impact. We've been trying to be pretty metered and pretty measured with how exactly we're rolling everything out and making sure that it does have quantifiable, valid, positive impact on the business, whether that's in in favor of chasing revenue opportunities or reducing costs, like both of those, all of those things matter.
SPEAKER_01So interesting. I love the practical nature of it. I think just giving us really very specific, this is exactly what I'm doing, is is going to be so helpful. Like everyone's learning this together. Just as we come to the end of this, it's been such a great conversation. What other advice would you give? We started with this, this is a dangerous place. I think there's a lot of things that you said that make it safer. What other advice would you give to someone who needs to be a rebel right now, to one of your peers out there as a product leader?
SPEAKER_00Look, I think it's the people around you. There's no sense in trying to be on a solo mission, so to speak. One rebel doesn't get very far, but you get a whole group of rebels together and it and it goes fast. And so I think that's what I've taken away from my career, as I can reflect back, is it's you know, get behind somebody else's good idea is equally as effective as having your own good idea and finding other people that believe you and finding those mentors, finding the people who are going to give you the room to explore and fail fast. And it's not gonna be, it's not gonna be a punishment on the other side of that. Which I guess said in a word is just like it's team, it's way more. That's why I focus so much on leadership and making sure that I'm bringing good people along for the ride and making sure that I'm always at risk of having somebody replace me because that means that we're just we're powerful. We can do a lot more together.
SPEAKER_02That's great advice. What's one thing we can brag about you right now? What do you what's one thing you're really excited about that you want to share with the audience?
SPEAKER_00I think we're where I work in the space I work in right now is high impact tutoring. And if I'm sure you follow the same news I follow. High impact tutoring is is having a moment. And the reason it's having a moment is because the nation, especially in our KA space, is in an absolute crisis when it comes to students' ability to read and do math in particular. Those are undisputed indicators of persistence and success and the ability to find yourself in the career and the life that you want as a human outside of education system, but complete your educational pathways and be successful in those journeys while you're there. And so we have built, and through random control trial study, which is awesome, right? That's usually talked about in pharma, not education. We've proven that our intervention can drive outcomes to the tune of 10% telepoint improvement on standardized assessments, which is something that is very difficult to be able to say. Because it was so successful, and actually this kind of goes back to our earlier conversation. We were listening to the market, and the market said, we love what you're doing with reading. Can you please do it with math? And so we brought math to market four months later. And we we did all the things we've been talking about. We went really fast and we broke things, but we got it to the market, and it is proving out to have very accomplible results. And I think it's just a killer opportunity to be able to play a massive role and to contribute to the tailwinds that this model is getting because there's so many other toys and tools in the education system that are simply unproven and a distraction. So I think it's really wonderful what we've built at Booknook. I think it's wonderful what our team is capable of doing, and I think it's an honor to be part of a mission-driven organization like this.
SPEAKER_01What a cool impact. Wow. That's what and what a great way to end this. That's kind of goosebumps. Congratulations to you and your space.
SPEAKER_02We're gonna fix it.
SPEAKER_01Uh yeah, please do. I hope so. Yeah, I hope so too. Jared, this has been an absolute pleasure learning from you, listening to you. Thank you so much for joining us.
SPEAKER_00Thank you very much again, appreciate it.
SPEAKER_01Thanks for listening to this episode of the Product Rebels podcast.
SPEAKER_02If you enjoyed this conversation and want to learn more from Product Rebels from companies like Netflix, Amplitude, and beyond, please follow us wherever you listen to podcasts and join us for another impactful interview in about two weeks.