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Maxine Anderson on Transforming Training through Text-Based Solutions

Product Chats Podcast · 2025-10-10 · 37 min

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Key moments - from our scoring

Substance score

57 / 100

Five dimensions, 20 points each

Insight Density12 / 20
Originality11 / 20
Guest Caliber13 / 20
Specificity & Evidence10 / 20
Conversational Craft11 / 20

Artist solves a fundamental problem in enterprise learning: employees want to learn but don't engage with traditional video-based training because it doesn't fit into their daily workflow. Founded by Maxine Anderson and co-founders Ryan and Michael, Artist delivers microlearning via SMS, Microsoft Teams, and Slack - channels where employees already communicate. The platform combines creation tools, delivery mechanisms, and analytics to surface learning gaps using AI, then pushes personalized, context-aware training at moments of need (e.g., a sales rep receives deal-specific coaching before a client meeting). Anderson shares the journey from validating the hypothesis that people can learn via text during college experiments with Stanford and Berkeley professors, through product-market fit challenges during 2022 budget cuts, to discovering stronger product-market fit with departmental sales and learning enablement teams rather than centralized HR. The platform now serves enterprises like HP, Google, and major insurance companies, enabling 80% of organizational learning - from compliance to sales training - through push-based, moment-of-need interventions rather than pull-based content libraries.

Key takeaways

  • →Text-based, push-delivered learning solves the core problem that most employees want to learn but won't proactively consume video training due to time constraints and poor integration with daily workflows.
  • →Artist uses AI to assess organizational and employee gaps, then generates and delivers personalized training recommendations to enablement teams for approval before pushing to employees - a push model rather than the pull-based personalization most AI learning tools use.
  • →The biggest scaling mistake is over-building product before validating that customers will pay for the solution; Artist validated manually and incrementally added features like SOC2 compliance only when required by enterprise deals.
  • →Initial product-market fit with centralized HR learning teams collapsed in 2022 when corporate budgets were cut, but repositioning as a departmental tool for sales and learning enablement teams (tied to revenue outcomes) unlocked stronger fit.
  • →Maintaining simplicity and a clear problem statement across pivots - rather than repositioning as a sales enablement tool - preserves optionality to scale across all 80% of organizational learning use cases over time.

Guests

Maxine Anderson

Topics in this episode

Sales enablementSlack integrationAgentic AI workflowsCompliance trainingProduct-market fit repositioningText-based microlearningPush-based learning deliveryMicrosoft Teams integrationSMS-based trainingEnterprise learning platforms

Questions this episode answers

How does Artist's AI personalization work if most employees won't pull learning on their own?

Artist uses an agentic workflow to assess employee profiles (tenure, deals, messaging gaps) and organizational needs, then AI generates recommended training that gets human approval before being pushed to employees via text or chat - a push-based model designed to overcome the 'pull problem' where only top 1% of employees proactively seek learning.

What is Artist's primary use case and customer profile?

While Artist can deliver 80% of organizational learning, its strongest product-market fit is with departmental sales and learning enablement teams responsible for driving specific outcomes tied to revenue, not centralized HR learning teams.

Why did Artist shift from centralized HR learning to departmental sales enablement?

In 2022, centralized HR budgets were cut sharply and HR learning teams treated Artist as dispensable overhead; departmental sales enablement teams with revenue accountability and tighter timelines provided stronger product-market fit and willingness to pay.

What was the core insight that led Artist from education startups to enterprise learning?

Maxine observed that traditional learning mediums (classes, videos, online courses) fail because they don't fit into people's real lives; text messaging - which 93% of the world's population already uses - removes friction and enables learning at moments of need while people are busy.

How does Artist avoid the trap of over-building product features?

Artist validates manually first (even texting people by hand in early days) before building technology, and only adds enterprise features like SOC2 compliance when customers explicitly need them to close deals, preventing premature over-engineering.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

12 / 20

The episode contains a solid origin story and several useful product lessons (e.g., avoiding over-building technology, the risks of roadmap-driven development, the importance of product perspective), but substantial portions are conversational meandering without new operational insights. The core ideas - hypothesis-driven development, validating before building, shifting from central learning teams to department-specific sellers - are sound but not densely packed; there's considerable throat-clearing and repetition throughout.

plans are useless but like planning is like invaluable
my job is to ship product that helps us win in the market and helps solve customer problems. It's not to run a perfect roadmap process

Originality

11 / 20

The text-based learning modality is genuinely novel in the context (circa 2020), and the shift from pull-based to push-based learning is a contrarian insight. However, the broader frameworks - hypothesis-driven sprints, finding product-market fit, pivoting go-to-market based on customer feedback - are standard startup playbooks. The confidence-shift metric as a leading indicator of behavior change is interesting but not deeply unpacked or substantiated.

how is there no learning, like, tool that uses text? The most common way of communicating to educate people
we were literally in a situation where we had a product and we had no market

Guest Caliber

13 / 20

Maxine Anderson is a genuine founder and CPO who has built a product from college startup through to enterprise sales with Fortune 500 logos (Google, HP, insurance companies). She has real operating experience across pivots, hiring, enterprise go-to-market, and product decisions at scale. However, she is not a household name in the B2B operator world and the company's stage (likely $5 - 20M ARR range based on clues) is solid but not exceptional at the time of recording.

we started ERIS in college
we've been building this for like, five years, working with large Fortune 500 organizations

Specificity & Evidence

10 / 20

The episode mentions specific company names (Google, HP, insurance company) and some metrics (35% average confidence lift, 80% of learning can be done via text, six interactions per lesson, 22-person team). However, these are lightly touched and lack detail: no ARR, growth rates, customer acquisition costs, deal sizes, churn, or quantified outcomes. The confidence lift claim is stated without methodology or sample size. Most of the discussion relies on conceptual examples rather than hard numbers.

after one learning experience, which is five lessons, one sent each day, 15 minutes of texting back and forth at most, um, after one learning experience, the average confidence lift is 35%
we're about like 22 people

Conversational Craft

11 / 20

The host, Rebecca, asks sensible questions and does attempt some follow-ups (e.g., clarifying whether experiences are personalized, asking how efficacy is measured). However, the interview is largely deferential; Rebecca rarely pushes back or probes deeper when Maxine makes broad claims (e.g., the 35% confidence lift statistic, the assertion that 80% of learning can be done via text). The host could have challenged the causality claims or asked for more specifics on customer outcomes. There are also few moments of productive disagreement or healthy skepticism.

So how do you show the efficacy of your application? Like, how do you guys. How do you know they're learning?
And if you were going the other way, it would have been a lot more painful

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A84%
  • Speaker B16%

Most-used words

product61learning49training26tool16build16based15sales15different15feel15organization14roadmap14learn13market13best12team12problem12

Episode notes

“What if the right knowledge reached people exactly when they needed it?” In this episode, Maxine Anderson, co-founder and Chief Product Officer at Arist, discusses how her team is redefining corporate learning through AI-driven, push-based training. What started as a text-based experiment at Stanford and Harvard has evolved into an enterprise solution trusted by companies like HP and Google to deliver the right information to the right people at the right time. Maxine shares how Arist scaled from startup experiments to enterprise clients, the lessons learned in product-market fit, and how simplicity became their biggest differentiator in a crowded e-learning space. She also explains how AI personalizes learning delivery, measures confidence gains, and links enablement directly to performance outcomes. Listeners will gain insight into the lean, hypothesis-driven product strategy that guided Arist through pivots, the leadership practices that keep a remote team aligned, and the future of scalable learning through automation and personalization.

Full transcript

37 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Want to take your product management career to the next level on your schedule?

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Speaker A: your team and organization. Get the world's most sought after product certification. Now available anytime, anywhere, foreign.

Speaker B: Hello and welcome to the Pragmatic Product Chat series where we tackle the biggest challenges facing today's product management, product marketing and other market and data driven professionals with some of the best minds in the industry. I'm Rebecca Calogeris for Pragmatic Institute, your host for this episode Today. I am really excited to have on Maxine Anderson who is both the co founder and chief product officer at Artist. Uh, and I'm not going to kind of like steal her thunder on her origin story, but we're going to talk about kind of finding, uh, founding and running your own company. We're going to talk about putting good product, uh, experiments and processes into practice, sort of eating your own dog food. Uh, and then obviously we're going to talk about AI and how that's really shifting things, uh, for the good and also keeping a lot of the same things the same even in the AI world. So welcome Maxine.

Speaker A: Thank you. Let's do it.

Speaker B: All right. I always like to start with origin story. Right. So how did you get where you are today? Why are you so passionate about what it is you guys do at Artist?

Speaker A: Yeah, so we started ERIS in college. Um, we actually. So me and my co founders all work in education. So personally I took a gap year after high school and I created an education program, like an after school program for kids in um, rural areas around Oregon, um, mainly to help them find their passions and try to create the impact that maybe, um, someone inspirational would create for you. Like when they create aha moments and you say, oh, I want to pursue that or I'm curious about that and basically spark curiosity. Um, and what I observed working first, I worked as actually a teacher, um, in those rural, in that rural area in Oregon. And I observed that a lot of the students couldn't, didn't have like a purpose for their education. Um, and there was an opportunity to solve a gap that traditional education methods weren't solving, I felt. Um, and so that's basically what I was pursuing. And I found that some teachers were really, really effective at creating like aha, moments for their kids. And then there's tons, honestly that are super burnt out and like those kids have really rough at home lives. And so I was trying to fill the gap and find out like, what's the responsibility of schools in these areas. And um, it was basically just like an exploratory year where I taught and I learned a lot. Um, and basically, you know, I, I think teachers are incredible. I didn't have the patience to be a teacher, but I understood a lot of the challenges all the way from kindergarten through like young adults. Um, and one of the things I did when I was there was I tried to teach a financial literacy class, um, for young adults. And I found like no one would show up. And I would put flyers for video training to go to. No one would show up. And I was like, everyone has this need. There's no way. No one wants to be financially literate. Um, but I think what I found was like, there's a, um, like social context component of learning where like it was uncomfortable for people to show the class or to pull that learning. And on top of that it just didn't fit into their life. Like a lot of these people would go to school and then they have other things going on and they're just not like being forced to go to these classes. So I basically had this moment that I was like, people want to learn, but a lot of learning methods in a way that like the mediums of doing learning, um, don't meet people's needs. Like candidly, right? Whether you're like a kid in school, whether you're an adult and you're busy, like people love to learn, everyone loves to learn. Everyone wants to get better and realize their potential. But like the mediums just don't help people learn that well. Honestly. So I went to college with this like problem in mind and like this problem set. And I met Michael and Ryan. Ryan was um, actually helping students, like uh, people around the world become better at public speaking. So like skill based education. And Michael was um, he led like a nonprofit series basically where people would host like business executives and um, create chapters at their high school to do that. And he was working with a student in Yemen and we all lived together in entrepreneurship, living community. And the student in Yemen said, hey, I want to open a chapter, but I can't access your materials because I don't have access to Internet. And, And Michael couldn't send him printed materials because he's in Yemen. He lived in a war zone at the time. And Michael and him, the Student, Yemen, both realized, like, we're texting each other, so I guess that's the medium that we can communicate. And so Michael started sharing knowledge that way. And I realized, like, hey, wait, I've texted my students to, like, share insights and things. And Ryan had been using WhatsApp to do a lot of the, like, training basically. And so we had this aha moment where we're like, how is there no learning, like, tool that uses text? The most common way of communicating to educate people. Like, it was such a simple idea that felt so overlooked. We, like, couldn't turn back. Basically, we're like, how is this not a way of learning? Like, 93% of the world has a phone. Like, no matter where you are in the world, most people can access a phone, which increases, like, education accessibility time. So anyways, long story short, we fast forward. We ran tons of experiments my first year of college to see if people can actually learn this way. We worked with professors at Stanford, at Berkeley, Babson, where we went to school, um, and Harvard to build, like, effective training. And we kind of started as like, masterclass over text. Like, learn from the best professor no matter where you are in the world. And it was really interesting. Like, people, we were manually texting people and like, they were opting out. Like, they would just respond and go through the training. We thought, this is crazy. Like, us and all of our friends, we love learning. But we couldn't get through one module on Coursera. Like, why? And it's because. Not designed around your life. Like, it's amazing content. Masterclass, amazing content. But it's like, so difficult at the end of your day to sit down and go through like three hours of training. Right? So there's definitely a place for that. But I think we discovered, like, oh, this is kind of an interesting way to learn, actually works. And a professor, he worked in corporate learning and he said, you know, you know, most of, like, people spend a majority of their life in the workforce and most growth and learning opportunities are missed because learning that's done in the workforce is video based. It's one time. And so we started doing research and found, like, there's tons of money spent on it. And honestly, it doesn't really enable people as much as it should to perform their best at work. Um, so that's when we started going after, like, basically working with companies. And that was in 2020. Um, and now we've been building this for like, five years, working with large Fortune 500 organizations. Um, and we still do work with like, nonprofits. And education groups that I care a lot about. So I lead those initiatives um, to help educate like in enterprises to help educate people to basically do their jobs. And what we have designed is essentially a solution now that understands context in the organization. So like basically if you know someone gets, is a new sales rep, they get assigned a new deal, um, then they'll get a text like right before their meeting saying hey, like practice these things in the meeting. Right. And so the point is it's like in moment of time it's the most important information you need and it's very action oriented to help people actually take action. And we found like incredible success with it all the way from like frontline employees, um, like literally in like mines, um, to people who are in construction areas to sales reps of pharma companies. So like there's tons of use cases for it and it's really cool to like bring a new way of learning to life. So that was a long story. But that's how we got to corporate learning. People always ask because we were like 18 year olds selling a corporate learning solution or like why were you born passionate about corporate learning? But that's how we got into it and it's really fulfilling to build um, a learning solution that like impacts someone's life.

Speaker B: So yeah, so let's talk about. So okay, so it's all text based. So it's not app based but it's text based.

Speaker A: We do deliver also over Microsoft, ah, teams slack. So whatever communication tool that influencer we

Speaker B: push to and is it generally like, is it reinforcement learning, is it onboarding learning? Is it like everyone has to take sexual harassment training learning, like is it all of these?

Speaker A: So we think about 80% of learning in an organization can be done this way. So we do everything from compliance training, like a certain subset of compliance training, um, through our main use cases are actually around sales product training for sales teams, customer teams, um, because those people are on the field and they need very important training about what to say about a product or things like that. So usually that's our main use case. Um, but we do everything. Like some of our customers, HP uses us for their onboarding programs. Um, so yeah, uh, we're also, you know, it's a new way of learning so we have to kind of shuffle our way through organizations and like what are you willing to use this for? And it's like a new concept for them. When we first started selling this a lot of companies thought video or virtual training was still like new. So there's like A whole, a huge jump from that. And so we've had to sort of create our own categories. Learning in enterprise organizations, which is a fun job.

Speaker B: Yeah, yeah. And I certainly with COVID that certainly forced the issue in some areas, which was a positive. But also, you know. Yeah, there were other obvious negatives. Um, so when you talk about the sort of how you guys leverage AI, uh, is this in? So there's, I mean imagine and maybe it's in again, all of these. The creation there is in the, in the experience. Like is my experience and your experience. If we work at the same company and we're both sales people, is our experience the same or is it tailored for me in different ways, like whether it was time of day or how frequently or how I did on some performance thing?

Speaker A: Yeah, yeah, that's a good question. So how it works is, um, so we have a creation, delivery and analytics product. Um, and it's meant to be like automated based on data points. So there's like an employee profile, so like context about that employee. When did they start, what deals are they managing just for a sales rep, for example. Um, like what gaps do they have, like in the way they talk on calls about like messaging frameworks. We take that data and then there's like what the company needs them to know, which is pushed to our AI tool. And our AI tool, what it does is it assesses organization and employee needs and surfaces that to the enablement team or the business owner of like that initiative or area. Um, and then it will generate like here are the gaps that exist, here's a recommended training. It will build that training and then it will like get human approval and then it can be pushed out. So we're a push based learning solution. Most learning solutions, especially AI solutions, are pull based, meaning they generate personalized training when the employee goes to pull them. But our thesis and what we found is that just like I observed in Laughter high school is that people want to learn, they just don't pull learning, no matter how good the experience is, maybe the top 1% of employees will pull learning. And it's largely because of time and how you're like every day you're so busy, right? So people want to perform better. But to actually pause and take time to learn is like really, really difficult for people to do. So we've optimized our product and how do we give each employee what they need to know, which it is personalized version based on the organizational context and what the people who have the central knowledge, uh, whether that's In a department like a sales enablement team or central learning development and what they have to push out to people. So it's kind of a combination of both and it's like we started on the learner side and then we built out admin workflows and now we're in a unique place to sort of streamline the automation and using AI. It's an agentic workflow across entire enablement um, stack basically for employees.

Speaker B: I think one of the other things that's really interesting and I was excited to talk to you about is that in your time at Aries, like you've. The change has been immense. Right. So you started up is full startup, right. University entrepreneur lab startup, few employees, you know, like let's get clients and see what happens. Right. To hey, we've got to be more predictable uh because they rely up. That's not the way it's like more predictable and more so because we have more clients and we've got bigger expectations of big deals. At the same time you've had sort of the, the, the COVID change which we talked about, which sort of change perspectives on online learning.

Speaker A: Mhm.

Speaker B: And also a uh, big change in AI which not only changes some of the capabilities you guys have, but I think it also really changes the questions and expectations from your clients. And through all that very busy.

Speaker A: Five years married me five years.

Speaker B: Right. You've led the product team. So.

Speaker A: Yeah, yeah.

Speaker B: So I would love just kind of thinking about like if you map out sort of how it's evolved and sort of the big lessons you've learned along the way as you've, as you've scaled during these very, very intense exciting times.

Speaker A: Yeah. Where to begin? Uh, it's been quite a journey. Yeah. So I'd say that the whole time we have been trying to, to solve the same problem which is like how do you get the right information to the right people at the right time so that they can do their best work basically like, and by work I mean like even when I taught like young kids. Right. Like work is like your life, like what you want out of life. So that is like very much has been our purpose the entire time. I uh, went to an entrepreneurship school, I have tons of other founders and I think the mistake is that you trade like the problem you're solving for the product you're building. M and we built like the product in the beginning was a very different model and a very different product. It was basically like a marketplace, like a, like a creation market, two side marketplace and like the, the challenge was that is like there just wasn't a market for that that allowed scale. And what we realized with texting is like, it's amazing for scale. And so I think how we ran things in the beginning isn't that different than now. But it was very experimental in the sense. Like we were very hypothesis driven. So when we built products in the beginning, we were like, okay, hypothesis one was like, do people engage with text and can they learn from it? Basically, right? That was what we were trying. If people can, then we have a big opportunity on our head. So we did that and we ran that experiment. We say in three months, if people aren't like engaging with this, like, okay, not disproven either, we change our product, we work on something else, whatever, right? So we ran a three month sprint on that. The next sprint was like, can people, like, can we convince educators that people can run this way? Because that's like kind of a rate limiter, almost like for getting the content out. And that failed. Like, that experiment failed because educators believe you need very high touch experiences. And they were college educators or had a very, were very set in their way, uh, in their model. Right. So I thought, okay, can you convince anyone else who controls the flow of information to people about this? And that's. And then we went after enterprise basically because their needs are slightly different, but they control ultimately that experience that employees have in an organization of like what information they get and how that enables them in their job. So it was an opportunity to solve our problem through like an interesting business model is kind of the way I think about it. But the product that we were building and the purpose of it was the same. The product has evolved a lot. Right. So we were like basically to validate those. In the beginning, by the way, we were like manually doing everything. Like we based, um, technology and like, I am the biggest fan of that. Like you think you're at the threshold where you need to build technology you don't like, you will have to validate. Like that is the biggest mistake that every single founder friend I've had is like, they really over build technology like always because it's fun. Like it's fun to build it. And even now I feel like I want to build this and I want it to be perfect and like that's a good standard to have. But it's a very dangerous business mindset. Like you need people, you need to be solving a specific problem and you need people to pay for that. Otherwise you don't have a business and you can't build a product. So like we went through that. But the interesting thing is so we solved this problem. We, we had like sort of probably. So then Covid hit. We sort of had product market fit. We were bringing on these big organizations and at first they were pilots. So I'd say we had some Lee room like our like freedom basically in the fact that like we weren't SOC2 compliant yet. You know all the enterprise features m you need. So it basically like product that. So I was like okay, what does every other learning product out there have? What do we absolutely have to build for them to be able to say they can buy this but still maintain our product value? So I basically did a sprout on that for literally two years. This was like the start of 2020 through 2022. The other benefit of sticking to enterprise is like the contract cycles are really long. Their implementation is kind of long too. And so we were able to like sprint to building out all of that while we were building on these like bringing all these customers. It was very like scary and like very stressful. But it was also fun and it worked out like the timelines worked out. And we also learned from early pilots they knew what they were using, right? So they didn't need US to have socket 2 compliance. It was like very early. The contract size were lower and so we basically work our way up like slowly increase like it's just been like a slow game. Like slowly increase contract um size and slowly add like more enterprise features. We got SOC2 compliance and like we basically have to. But what happened is we spent two years doing that. We had amazing, we had great logos, like huge insurance company hp. We had Google like honestly like my co founders grant selling. So we had really lows Covid people needed something like this. Mhm. We raised around 2022 and then we thought we had product lineups too. We said we bring all these customers, all these central learning teams are buying us. It's like perfect solution. We're just going to scale within these customers. And then like all these companies basically pulled back their budget, especially HR teams which like their budgets get slashed first. So they pulled back their budget and we were basically just like this extra tool that had to get slashed. So we were like what do we do? Like it was like 2022. We thought we had program fit and at that time like we had this product and then we faced the opposite problem, right. Which was not like, which was what we told every founder not to do which was like don't build a Project and find a market right like right. Find people's problems. But we had, we were literally in a situation where we had a product and we had no market and we were like what do we do? So we basically just like talked to a ton of people, had these teams introduce us to like maybe other people in the organization who might want to use it and we found really good, much better product market fit with um, sales enablement teams or like learning teams that were under a specific department and the reason being is that they're responsible for driving a certain outcome in a certain amount of time and it's tied to revenue and eras is a great solution for pushing only what people need to know. Not a content library. Check the box. Like we have this training which central learning teams need. So we basically change our entire go to market function when after all of these people and I and we definitely evolve the product to have features that meet those audiences a little bit better. Mhm. And so we did have to add those products. But the way that I've built product which is a risky, maybe not like the best way we'll see how the bet plays out is like long term. We do believe that like 80% of uh learning can be done this way. And the more administrative side like agentic workflow we figure out the more you don't need to rely on the central learning team to deliver learning organization. So each like function can use us. Therefore we are a generalized tool for like just the best tool for push based enablement in an organization. So I've actually never, I viewed sales enablement and like that part as a really good use case for ERIS and making that use case obvious in the product. But I didn't reverse our product and say oh now we're a sales enablement tool and like who knows maybe like that that won't play out but like we didn't do that. And we also went after a life science company, added some like compliance we needed for those. But like we really like simplicity is our biggest principle and values. Like our, our solution is quite simple. We're literally texting people what they need to know. Like doesn't matter about learning styles. Like we've abstracted a lot right. Like just put the information in front of people that they need to know and it's like it's like 10 times better than most solutions out there. And so same thing with like our go to market approach. It's like what is like the thread of what people need across all these use cases and how can we build products for that and make the pathways easy. But long term still enable what we're trying to work towards which is we believe that 80% of learning can be done this way in an organization. So that's kind of been our path and like you know the, we've had moments where we're sprinting on product and then moments where we have this product and we're sprinting on go to market. I think that's just natural in a startup. And now we're finally in a place where it's like coming together. We're building out like way more AI into our product. We're super well positioned because we're like a conversational uh, tool and we're tech specific space. We're starting to generate like more videos and podcast style learning. But um, but yeah, we're just really well positioned. So we were one of the first companies to use OpenAI as like LLM when they let people use it. Um, and we created our content creation tool that generates content based on existing content. We're the first tool that did that. Now it's like every elearning tool has that but we are the first tool that had a ah, content creation generation engine with AI. So that's been our journey. Um, I think you asked for lessons but maybe there are stranger out there.

Speaker B: But no, no, that was great and it was really interesting to see both how the product has evolved and how the market evolved and some of that is responsive but I mean that is the truth, right? You, you're starting education. The next closest sort of Persona to that in the corporate world is your learning and development people. But it is a truth that their budgets go, go way faster. Uh, and they're smaller. Yeah. And, and it's also interesting because I imagine both in your feature set and your conversations, the things that lnd cares about, the things they talk about, the, the requirements they'd have and show in, in terms of some of the like you know, learning best practices that they want to see reflected is very different than when you're talking to a salesperson, sales enablement. Like they have very different measurements. It's, I mean they both want the same thing at the end of the day but the terminology, the measurements, all of that that they use to get there is very different.

Speaker A: Very different. Yeah. Then I think we went from a more robust criteria to people who are just looking for an outcome I'd say. Yeah. And uh, so that was actually a really like, I'd say we were lucky there. Like I don't know that that's true for every time you change who you self tip.

Speaker B: And if you were going the other

Speaker A: way, it would have been a lot more painful. Painful. Yeah.

Speaker B: So how do you show the efficacy of your application? Like, how do you guys. How do you know they're learning?

Speaker A: Yeah, so a few things. So one is, um, we're always like the holy grail. And this is for any learning tool, but I think we're a little bit better positioned to do it is to show that people are actually performing better in their jobs. Right. So if you're a sales rep, obviously, like you're either closing more deals in the final stages that you're struggling with, or you're handling objections better. Like whatever the objective of that course is, you're doing that better. Right. Um, so we look at a few leading indicators towards that. Like of course we track engagement, whatever. We try to not index on it too much. Uh, but what we do look at is we found that the biggest predictor of potential behavior change is confidence shift. So in the way that they respond, um, like their tone, like our AI evaluates it or how we're actually like marking it, like they'll self report their confidence. And on average, after one learning experience, which is five lessons, one sent each day, 15 minutes of texting back and forth at most, um, after one learning experience, the average confidence lift is 35% with our tool, um, which is quite high. And that is the biggest correlation to behavior change. Often especially with management training and things like that, the confidence lift drops at first because they thought they were great managers. And then they go seeing feedback course and they're like, we're not. So that's like the first level of like a leading indicator we look at. Obviously if you're like following learn. I don't know how much this audience knows about like learning and all that, but like Kirkpatrick model is kind of like you have sentiment. Do people like it? Uh, are they practicing? Okay, so of course we follow that, but let's like skip that and say, okay, now we're at confidence, then what we look at is we actually pull. Our agent will pull data from other tools to understand. Like pull data from gong and surfaces that say, okay, this person is still missing these three pillars in the messaging framework on like every call. And that's a risk. So of course I'd say like, if I'm being completely candid, are like integration across an enterprise customer base quite varies. So like the value we provide without integration is mainly just like we have tons of data points on like learner response data. Because they're like every single lesson is like six interactions that user. Right. So like most learning tools they click a few buttons but you're not getting like the open ended. What people share over text. People share a lot more over text. So it's actually more like valuable information that gives you a pulse on the business. So that's like without integration we use that to surface like potential business risks or like hey, everyone under this manager isn't comfortable like giving feedback to like their manager, like bringing things up on the team. That's a business risk. Right. So that's one. But then the integrated data, once we can get integrated with customers, we do try to pull insights and then surface actual like gaps or like outcome changes. And we basically like how we operate. Like the workflow we've developed is like the business owner goes in and they'll share, hey, this is the uh, experience or like this is a business problem we have. So instead of saying this is a training need we have, it's like here's the business problem. And then our agent runs a needs analysis process. So it interviews tons of people, evaluates data internally. Then it surfaces gaps and it says here's our recommend training, we're going to create it or do training elsewhere. Right. Then you launch the training and then it tracks against those gaps. Like are those gaps being fulfilled based on like data and evidence or like there it's still like open for all these employees. Like it's not doing anything. And sometimes like training isn't actually the right solution. And you'll talk to anyone on our team, they say Yeah, I get 40 requests. I was talking to like um, literally yeah, like one of our customers in Mid Marketplace where they're like, they get like 60 requests a week from other business units on like training needed to like solve employee problem. Like their employees not performing. It's like there's no way that like all of those are actual like training is a solution.

Speaker B: Not always a training issue.

Speaker A: Yeah, actually always a training issue. And so we also tried to like how can we help the organization enable employees like not just through training. And so we started to get into that like higher level anyways that's moving away from sort of how we measure success. But yeah, we always try to look at like performance indicators. Whether that's like our customer success team which is like very consulting heavy or it's like in our product. Either way you have to understand the business really well to do that. Well. Yeah, yeah.

Speaker B: So the other, my other question would be Around. So your founders have been together from the beginning and clearly you were all in this at that startup stage where it was an idea and let's see if it has legs as you get larger and you have more of a team. How do you keep, um, how do you keep everyone aligned with that spirit? Right. Because there is the. Yes. We need to be agile and fluid and responsive. It can also feel chaotic and ah, unorganized. Right.

Speaker A: Yeah.

Speaker B: And depending on your point of view in the organization and the amount of understanding you have. Right. Um, so how do you, in terms of talking about roadmaps and changes and those kind of things, how do you keep the organization aligned with where you're heading and why and what may change along the way?

Speaker A: Yeah. So I think, I think that what. I've definitely not done this. We haven't done this well forever, I'd say, especially in times when it wasn't.

Speaker B: You are not alone. Yeah, let's put that out there.

Speaker A: I think roadmaps and startups are valuable for vision alignment. Mhm. I think other than that, uh, they can be a little dangerous because you get into, and it's happened to us for I'd say an eight month period, you get into a cadence where you're optimizing for roadmap delivery and not like business success or like solving people's problems. And sometimes they, they definitely overlap. But I always, I found this and it was like uh, this quote. I love it. It's like plans are useless but like planning is like invaluable. Like it's so helpful. And that's how I feel about roadmaps. Planning is like how you're getting toward a vision. The plan of a roadmap is like, unfortunately, as much as I'd like to, you know, commit to and everything's perfect, it's just like super unrealistic. So I, as much as everyone in the organization might not agree, I like set that expectation internally. I'm like, hey, my job is to ship product that helps us win in the market and helps solve customer problems. It's not to run a perfect roadmap process. It feels really good. And that's the thing in startups, especially with product. So many things feel really, really good. And unfortunately so much good product work doesn't feel really good, does it? It's like you're fighting with stakeholders. You're like taking a bet on something and people are like, why aren't you fixing this other stuff? Right. Like I felt like our best product work is like, it just doesn't feel that good. Like. And I could go on a tangent about this. I think there's so many helpful frameworks for product and I think it's a very complex job and it's very different in every organization. But I think product is just. It's such an art. And I don't. I think frameworks can be super limiting. Like learn the framework so you know, like the general science of it. But then like, get yourself out of that and know what your job is. Your job is to like make money, like for the company. To like people to pay for what you're building. Building. Right. So anyways, I'll start it. But yeah, so that's vision wise. Like what I found successful is like one setting expectations properly. I used to like over promise all the time, which is a really dangerous place to be and don't do that. But every PM goes to that. I feel like, um, especially founders, because you're so excited about the vision and you're like, yes, we'll have this next. Like, I think being a founder in a product course is actually really dangerous and you're way more likely to over promise than not. The second thing is that, um, I do work with our CEO and I make sure that he's like representing our vision and how our product roadmap aligns with that. Like we both will do that like every six months for the company. And then, um, I try to do like have a central place where anyone can go in and look at the roadmap, like how it's. How it's evolving and whatever. M and then work for a small team. So like, we're still pretty lean. We're about like 22 people. And so I think that like it's easier in our size, but we are remote. So I actually try to do more deep dives with CS on like, what are the top 10 problems people are experiencing? Um, how can we deliver? Like there is value to delivering satisfaction even if it's not like exactly your product vision. So we try to figure that out. And then with sales reps, I'm like, why did we lose these like deals from the last quarter? How are we going to win the next ones? And I always do sessions like that. I think like more in depth conversations where people are realizing why you're building things is more valuable than presenting a roadmap. I always try like roadmap presentations and it just like sometimes it's like they need a feature for their deal. They don't really pay attention. I feel like the most valuable thing is like what do you think we should build? Like, why? And they come to kind of their own conclusions about like our perspective. I think product perspective makes roadmap features obvious. Like yes, uh, no, we don't, we are, we don't build like an in house video hosting tool because we are a push based product for like quick insights. We're not 10 minute video product. Like really sharing perspective and getting people aligned behind that is like more valuable I think because then they obviously know, yeah, we're not going to add a feature where you like annotate a video ever. Yes, ever. It's just not a product perspective. So I think that's like a really helpful way to get vision. I think between the three of us, because you asked the co founder question, I'd say luckily our vision's always pretty aligned. I think the strategy on execution, how to get there is different because one, like you said, we all have different contexts and two, we're all very different people. But like we share the same purpose and that helps a lot. Um, and just like I think tough conversations, like we try to meet like every month and just talk about like what our anxieties are and what we're concerned about and that helps a lot. Um, but we all have different data points from like product perspective. And I'm always the one who has to be like, no, we're not doing that or yes, we are, whatever. So, uh, yeah, product is a tough, tough job.

Speaker B: It is a tough job.

Speaker A: Yeah.

Speaker B: Best job.

Speaker A: Yeah.

Speaker B: Uh, so what's next for you guys? Where, where, where does like the. Not don't tell me your roadmap, but like, what are you most excited about next?

Speaker A: Yeah. So we're at a point now where like people are, are using our product for a wide variety of use cases, which is exciting. It took a long time to con people to even like use it for one because it was like such a crazy way of doing learning in some people's mind. Um, we now have the opportunity. Like I think our product is best designed for scale. Like I think if you have 10 people on your team, like you should just, you probably should just talk to them and teach them. I mean, honestly. Right, but.

Speaker B: Very true.

Speaker A: But if you have like six regions of sales reps where there's a hundred sales reps in each region, like you can't possibly give them each a coach. Like, even with AI, like it's just, it's really hard to streamline. And I think we're in a unique place to like really change the way the information Flows from like a learning perspective in organizations. And I think that enables the potential for one, like companies to move a lot faster and two, for like all employees later, frontline in the field at the desk to like feel enabled to do their job really well. And I think that's really exciting. Like, I think people always feel like they like can't keep up in their job or like if you're part of a learning team, like you can't deliver results and like you just feel like that your whole career. And I feel like we're in a unique place with like automation, AI, ah, adoption and the product we built to really streamline that. And so that's what we're working towards now in the future is like, I really think the reason that people can't get the right information, the right place, right time. I used to think it was like learner driven and modality, but I feel like we solved a lot of that and now it's like, how do you solve organizational red tape and challenges around organizing stakeholders, all of that. And that's a hard, complex problem. But I think we're well equipped to solve it. And I think that is really our focus over the next few years because that's ultimately what prevents employees from feeling like they have what they need to do their jobs well.

Speaker B: Excellent.

Speaker A: Yeah.

Speaker B: All right, Maxi, we talked about lots of different things.

Speaker A: Yeah.

Speaker B: If you could have listeners do two things differently tomorrow based on what we talked about today, what would it be?

Speaker A: Uh, one, reevaluate your roadmap and like look at it and say, like, what on this roadmap is like making our company like 150% it's going to succeed. What on this roadmap is really driving success. And two, make sure that you have a perspective that you could sell anyone about your product, a strong perspective because it makes product. I didn't actually for a while we need to have this. It's so easy to get overwhelmed. And I think that having a perspective is like really the best way to build an effective product that like cuts through the noise. Um, because it's really fast to build product now and really honestly easy. And so like perspective and like design and product sense is like really the differentiator.

Speaker B: I feel like, I feel like those two kind of go hand in hand too. Right. Because you have the, um. What is. If you have a perspective or the point of view about what is distinctive and differentiated.

Speaker A: Yeah.

Speaker B: Right. This is who we are and what we solve. Then you look at your roadmap and go, okay, what one thing on that roadmap really helps us, like, either build that promise or reinforce it, because that's the thing that cannot move on 100%.

Speaker A: Yeah.

Speaker B: Right. And that's the thing I have to fight for versus, like, there's all the, you know, there's technical debt, and there's, like, there's a lot of stuff. But that those two things and understanding that going hand in hand makes a ton of sense.

Speaker A: Sense. Yeah. Cool.

Speaker B: Awesome. Well, this was great. Maxine, thank you for joining us today.

Speaker A: Yeah, thanks for having me.

Speaker B: All right, that does it for today's episode. Thank you, everyone, for listening. And don't forget to join us next week when we tackle, uh, another great topic designed to help you elevate your product, your company, and your career.

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