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How a Product-Led Company Utilizes Storytelling Instead of Feature Pushing

Kyle Lacy, VP of Marketing, Lessonly

Does product lead marketing or does marketing lead product?

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Anna: Does product lead marketing, or does marketing lead product?

Christian: On today's show we sit down with Kyle Lacey to discuss the answer to this very question.

Christian: Now, whether you know Kyle or not, a quick search will pull up his accolades. He's written books, he's an international speaker. He's truly a marketing thought leader. In 2017, he took on the opportunity to join Lessonly, a software company in Indianapolis, as their first VP of marketing.

Anna: And outside of exploring this question, does product lead marketing or does marketing lead product, we'll learn how Kyle launched a user conference that didn't feel like a user conference, a conference that he ultimately didn't get to attend, as his wife ended up having their second baby a bit earlier than anticipated. He also shares with us how they doubled down on their brand messaging, while making sure the company never lost the voice of its founder, Max Yoder.

Kyle Lacy: The vision for Lessonly from the very beginning was, we help people do better work so they can live better lives.

Anna: So for him, it was about taking the company to the next level by telling the Lessonly story. Hear how they focus on taking an internal conversation and made it external.

Kyle Lacy: It was more about taking the story and putting more of a foundation around it. So it was, how do we take everything we talk about internally, make it external so everybody truly understood what Lessonly's all about.

Christian: When you think about taking on a new opportunity and a new role, often people in leadership positions will come in thinking they need to make their mark, make a huge impact. They think that kind of starting they have to have it all figured out. But in fact, Kyle shows that he spent his first month just kind of observing what was going on.

Anna: He didn't come in with an agenda. He didn't come in with a one-year strategy plan. He started with a really simple objective, just listen and learn.

Kyle Lacy: I'm not a huge fan of the idea of having a strategy that you implement in a high-growth software company. Because the things we talked about at the beginning of the quarter changed dramatically throughout the quarter based off of growth, because you are growing so fast and you're bringing on customers at such a rapid pace.

Kyle Lacy: So right or wrong, I've never had a core strategy that I've implemented. It's been, here's what we need to accomplish in six to 12 months. Here's what we need to do to get to that point in the three months we have ahead of us. And then we change it along the way.

Christian: Looking at that, so you said in six to 12 months you kind of have an idea of what you want to happen. What were some of those things in your first year, in 2017?

Kyle Lacy: First one was have a conference.

Christian: So what drove that? The having a conference. What was the-

Kyle Lacy: They had been talking about it. It was mostly just taking the risk to do it. And I just, I'm a fan of just, if you think it's a good idea, and it somewhat aligns to strategy, then do it. The conference made sense to me; it was a good way to put a stake in the ground to say we're serious, and we want to make it different than everybody's else's, doing just another user conference.

Kyle Lacy: There was that. There was the doubling down on our brand and the voice of our brand, and making sure that we spent as much time as possible getting what Max portrays to the market into us, as Lessonly as much as possible. Because if we lose his voice throughout the product and throughout the market, then we lose in my opinion.

Christian: What's in a user conference that makes it a useful marketing tool for companies?

Kyle Lacy: What makes a conference valuable to a company is the face to face interaction between the customer, the prospect, and the company. It's a good way to get everybody in the same room, and we just took a different approach; we didn't spend a ton of money on a speaker, we had some really cool speakers that delivered impact. And then we had a lot of practitioners that did breakout sessions. And it was really just about the relationship and making sure that we could get across our do better work message.

Anna: Why was it so important for it to be different?

Kyle Lacy: Because Lessonly is different.

Anna: Okay.

Kyle Lacy: We just have a different approach to business. I mean, my first couple of months with Max, who's my boss, was about, talking about appreciative inquiry and nonviolent communication. Like, it's just not normal. I wish it was, in a lot of companies. I mean it's just, the way he approaches things is the ethos of Lessonly.

Christian: What worked about Yellowship last year that you want to bring forward to the next conference? And conversely, what are some things that you're hoping to improve upon?

Kyle Lacy: You know, improving upon the conference is going to be about creating new experiences. We actually lucked out that, we didn't have many complaints, other than I think the chairs were uncomfortable for people. Like, that was it. So it's more about how do you expanded upon the experience so it's different than other conferences? How do you make sure that the product offering that you are showing at the conference isn't like a full-blown product demo, because we don't want this to just be another user conference where you're talking about, here's what we built and we're going to build in six months and blah blah blah. Like, I want it to be an experience and not just we're going to sit and listen to somebody talk about a product.

Anna: How do you experience a product without sitting through a product demo?

Kyle Lacy: We did it at our last conference by building it into the Do Better Work methodology. So there are six pillars to it and we showed six different product offerings that we had built, or were building, that apply to the Do Better Work methodology. So, the Do Better Work platform. And that got us away from like, just demoing something and getting your product person up there and doing it.

Kyle Lacy: So just one thing to make clear on Yellowship. We do think about it as a conference, which is why it does help us keep the product from being front and center. I mean we had 380 people attend over the three days, and we had 400-something customers. We're shooting for 500 next October. We want it to be a conversation about how people can do better work, because we work [inaudible 00:06:40]. That's what we do, right? Most of us. We work all the time, right? Most of our day is working. So why not have the conversation about how you can make work more enjoyable for people.

Anna: I think it's super interesting, you mentioned the Yellowship brand, and how it's not a product conference, it's a conference. Like, it's not a user conference, like you said. So, how did that affect how the brand execution of Yellowship?

Kyle Lacy: I mean, yellow is our brand color. We wanted movement to be involved in the conference. Yellowship is easy to say; we actually liked saying it. The URL was open.

Anna: That's always important!

Kyle Lacy: Yeah. It was just a different way to brand a conference.

Anna: Any challenges that you didn't anticipate with the conference?

Kyle Lacy: Our biggest thing was just making sure that the story was told in a way that made sense to everyone. We'd spent a lot of time and energy trying to build that story. How do you fit the product into that story? How do you fit the soft skill Do Better Work side to the actual tactical side of doing better work in the platform? That was the hardest part. And I didn't necessarily see, I knew it was going to be hard to do that, but it was harder than I thought.

Anna: How so?

Kyle Lacy: It is difficult to try to get a bunch of people in a room and tell a story in a unique way that Max feels confident delivering and that all of us are behind.

Christian: And what did you do after the conference? How do you ensure that everything you've done there, that you're sort of leveraging or carrying the momentum through on the marketing side for the product?

Kyle Lacy: So, the most important part about leveraging momentum at a conference, at Yellowship in particular, is to make sure that the Do Better Work message is being now applied through everything: onboarding [inaudible 00:08:27] customers, the products, our messaging to the market moving forward. We put together a Do Better Work committee internally at Lessonly that has leaders from each team, that meets on a biweekly basis to kind of do quarterly projects on how they get the Do Better Work idea internally into Lessonly, as well as externally in the market.

Christian: Where did Do Better Work, the actual words, come from?

Kyle Lacy: It's the mission statement that Max wrote five years ago when he started the company.

Christian: So when you came on, it must have existed?

Kyle Lacy: No it didn't. We actually went through a couple of different ideas of how to bring the message of Lessonly into the market. The first one I came with was The Knowledge Divide, which was like, the fastest performing teams in the world compared to the normal businesses and what the gap is, and we believe the gap is continuous training, which-

Christian: That sounds like a great book title too.

Kyle Lacy: Yeah. It was great. Except, it just fell flat with everyone, right? Everybody, pitch decks. And then-

Christian: Sorry, because when you say everybody, was it ever tested externally or-

Kyle Lacy: Yeah, we had pitch decks. Max did it at a couple of conferences. I did it at a couple of conferences. And I think the messaging was good, but The Knowledge Divide just did not fit with Lessonly.

Christian: The way that I kind of look at this conference too, it's almost as if it's like the launch party for a new messaging.

Kyle Lacy: New messaging. And I think any software company and product-led any company, especially software, you either do high level messaging that captures imaginations of a lot of people, or you try to create a category. It's not something that we wanted to pursue, because we serve so many different types of people: sales enablement, customer service training, learning and development; that we wanted to go more broad. So it's a different strategy.

Anna: How do you feel like that is an advantage, and maybe in some ways a disadvantage?

Kyle Lacy: I don't know how it's an advantage yet. It's definitely a disadvantage, which we are constantly looking at. We kind of bridge that gap with review sites like G2 Crowd and TrustRadius, where it's more about the customer reviews than it is an analyst's opinion on where you fit in a quadrant. It's definitely, I think as we start expanding as a company, moving into larger deals and upper market, we definitely are looking at categories. We just don't know. So we're trying to bet on something that we believe is true right now, and evolve that as the market changes.

Anna: You mentioned the website overhaul, and you call it simplifying, simplifying the brand, simplifying the message. And then you also mentioned you guys really were very B2C inspired, as opposed to looking at other B2B websites, which you did as well. So I guess tell us a little bit about that.

Kyle Lacy: We spend so much time as consumers in our day to day lives that we do not apply them to marketing tactics in our day to day as B2B marketers. Like, if you go to a lot of the largest B2B marketing sites in the world, like software companies, they're just a mess.

Christian: Why do you think that is?

Kyle Lacy: They have a lot of product. They have a lot of people. It's harder and harder to simply it as you get bigger. But for us it was, one of our tenets as a marketing team is obsess over the experience. So obsess over the prospect experience. If they come to the website and they have no idea how to get in front of a salesperson to make a buy, you've missed it, right?

Kyle Lacy: So, I give a lot of credit to Mitch Causey, who's our director of marketing, but he said we should remove all forms and only do one CTA, which was get a demo. And that way you're opening up all of our content to more eyeballs. It's free for everyone. And if they want to get a demo they get a demo.

Kyle Lacy: And like you said, we looked at a lot of consumer sites, we looked at some of what we were the top B2B software sites, and realized that simplifying the messaging, simplifying the UI, simplifying everything about the website, was the most important thing we could do.

Anna: What do you mean by simplifying?

Kyle Lacy: Like, not having 60 forms. Because somebody that downloads a template for a training guide, that does not mean they want to buy training software. It just means that they need a guide for training.

Christian: So what do you think drove the decision to gate the content to begin with?

Kyle Lacy: Leads. Having more volume of leads is better. And it took a lot of energy for us just to say we're okay with getting less leads. But what we've found is that we're actually getting more than what we thought, and they're more qualified.

Anna: Why did you say that took more energy, to get more leads?

Kyle Lacy: Because you're seeing leads go up, but that's great, because it makes you feel great, but then if conversion's going down, like, who cares about the volume of leads you're getting? So we just thought, let's simplify our idea of a lead, which is a demo, and all the demos we get are qualified. And that allows our inbound team to work more effectively, because they don't have to process through all the crap that we were getting before, and it allows our sales team to believe in inbound again because they're more qualified leads.

Kyle Lacy: But, at the core of it, it was, how do we make the experience as simple as possible. Like, it's amazing that marketers, like everyone that we think that just because somebody filled out a form, they want to buy it. And I fully admit that I was that type of marketer and I had to be pulled around. But it works, because it's working for us.

Christian: It's interesting, because earlier you were talking about up-leveling and going upmarket, larger clients, getting more clients and broadening. And you're a B2B, SaaS company. I think a lot of times we meet B2B SaaS companies, they typically think business speak, feature first, talking in that sort of way, but you're saying when you rebranded, when you're up-leveling, you're getting back to some of the brand voice that's more honest. How do those two worlds collide? Because it seems a little bit against what there's conventional wisdom around in the B2B world.

Kyle Lacy: Yeah. I mean I'll go back to consumer. I mean think about, if you're searching for a flight, you have how many options to try to find a flight? A ton of options. Brand plays into that. It's the same thing with software. A feature does not sell software anymore. There's just way too many competitors; the market is wide open. It's your ability to tell a story that delivers a different value to somebody than just a feature set. People ultimately want to work with people they enjoy. With today's software world, you can buy from anybody you want.

Kyle Lacy: But that's the value of brand. If you can tell a story differently they're going to listen to you. And we just happen to be able to tell a story differently in a way that works. Now, from a features standpoint, you have to continue to work to be on par with your competitors so you don't lose the feature battle after you get the lead.

Kyle Lacy: And B2B software companies sometimes think the exact opposite. They're like well, we're going to sell our feature and then hopefully we get the deal through the sales process. We're saying, you tell a story first, they fall in love with you, and then the product delivers on the values that you're trying to sell through the top of funnel.

Anna: How do you continue that story into the product?

Kyle Lacy: The hardest part about including the messaging within the product is the question you have to answer, does product live in front of the message or does the message live in front of product? So is marketing tailing product releases, or is marketing out front of product releases before they're delivered? They're two very, very different strategies.

Kyle Lacy: We tend to go about the idea that if we understand the market correctly, we are a product-led company. Where, product is out front of the needs of the customer, and marketing is delivering on the messaging in one holistic approach. A lot of people just talk about, here's the product we're going to build and it's not built for 12 months, and that is not product-led, that's marketing-led. Which I think has worked in the past and does not work anymore.

Anna: So in your experience, when do you recommend a company should start thinking about product marketing?

Kyle Lacy: It's really dependent on how the software company was built. For me it's more around middle of your Series A, Series B raise, when you start investing in product marketing talent. And that's because you're getting to the point where you've found product-market fit, meaning that it's repeatable and it's scalable, and now it's about truly understanding competitive set, win-loss reviews. Understanding what the market needs from a customer standpoint, which could live between product management and product marketing. And it's also doubling down on new industries or new verticals or segments that you might not have thought about before. Because you're starting to find repeatability in the process.

Christian: What was Lessonly like when you came on?

Kyle Lacy: We had a targeted approach to go to market. We had an outbound sales team. It was about reaching out to people to get them interested in the product. And to sell the product. And the way you go to market in that way is much different than if I was at a Typeform or a Mailchimp, where it's about volume. Where somebody can do a free trial, they can start using the product. You have automated onboarding and everything. And Lessonly, it's more hands on. The CX team is much more involved because that's our strategy from the very beginning. And it's just a different approach to marketing. You spend way more money on organic and Google Adwords from a product-led company, 'cause it's cheaper, than like, spending money in an outbound sales team.

Christian: Have you found in your time at Lessonly, has product marketing impacted other internal groups? The way the product is sold, how the product is built?

Kyle Lacy: Product marketing is involved in all of our win-loss reviews. So that has impact for the sales team. Product marketing is responsible for a lot of the product enablement. So that means we use Lessonly as a software to enable our sales and CX team on our roadmap. So here's how you talk about our Zendesk integration, here's how you talk about our practice features that are launching. Here's how you talk about X, Y, and Z.

Kyle Lacy: And then product marketing from a competitive standpoint, we keep our Lessonly lessons up to date on the competitive standpoint so that, you know, if a salesperson is dealing with a competitor, they can go to Lessonly and take the competitive lesson, to make sure they fully understand why we beat them. It's like a battle card for us.

Kyle Lacy: So, it touches pretty much all parts of the org. And it will only get more ingrained as we grow and we add more people.

Christian: So as you scale, looking towards the future, what does that look like for Lessonly?

Kyle Lacy: It really is doubling down on what we have done. It is fully understanding if product marketing will get more robust as we enter new markets. Like, I'm not saying this is going to happen in the next year, but as we open up new markets like APAC and UK, I mean it's just a normal thing, Canada, as you grow. You know, that's going to open up new competitive sets, it's going to open up new niche players that we might not have seen before. From a product standpoint, as we move into larger deals, which we will continue to do, the product landscape changes dramatically. Because you have needs that you didn't know existed because they are huge organizations. And I think product marketing being involved in that is important. To fully understand the enterprise buyer is a completely different thing than what we're dealing with right now. Which we would continue to work on.

Kyle Lacy: And then we're doing another up-leveling of the brand, to invest in getting Max and Connor out more in front of people and speaking and the book and really trying to own the conversation around how do you help employees enjoy what they do, and Do Better Work.

Kyle Lacy: It's funny that we as people admire musicians and athletes, and we even practice. Like, I run, I practice running because I run races, right? And we don't do that at work most of the time. It's really interesting that salespeople don't practice, customer service people don't practice. And at Lessonly we believe that practice is actually the most important part about training. And that's kind of what we're doubling down on in 2019.

Anna: So, what does better product mean to you?

Kyle Lacy: Better product meets the need of the customer better than it did before, in ways that only the customer could tell you. And it's really customer-led type product development. Because your customer is your best salesperson. And if you can deliver a better product to the customer than what they bought, they will stay with you. And in the software world, retention is everything.

Christian: That was Kyle Lacey, VP of marketing at Lessonly. The best place to learn about Lessonly is, and the best place to learn about their user conference, which is coming back October of 2019, is And of course the best place to learn about Kyle Lacey is on LinkedIn.

Anna: Christian and I sat down and wanted to rehash some of the things that he said. He made a lot of really good points and wanted to kind of hit those home. So, enjoy us discussing these things!

Christian: The first thing that resonated with me was, obviously we knew here locally in Indy, we knew about the Yellowship Conference. But when he was talking and he was tying it to the messaging of, Do Better Work, it really struck me how to pull something like that off, you have to have a strong brand. Because, he wanted to make a user conference that wasn't like a user conference, and that came through. And when Yellowship came out, I don't know that I even knew that it was Lessonly to begin with. It just looked like a great conference. But to pull that off, to be genuine, you have to have developed an honest brand, and I think brand ties into something like that really strongly.

Anna: I think it speaks that the honesty of the brand, trickles down from the authenticity of Max as their CEO, was really interesting.

Christian: Yeah. Totally. And I think when you read about startups that have a founder that has a distinct vision, really the growth of the startup, the success kind of is determined by how well you can scale that vision down throughout the company. And what's interesting with Kyle is he wasn't there from the beginning, he came in a few years after Lessonly had started. He's been there for a couple years. And he got what Max was trying to do and could execute on that. But I think that's part of being honest, is like, a lot of the keys to your product's messaging, even when you scale to new markets, is really rooted in what it was to begin with. And just finding new ways to tell it, new stories to tell. And I think that's kind of what Yellowship was; it was almost like a package around the vision that they'd always had, but buttoned up and more formalized.

Anna: Something else that was really interesting about that too is, how they are doing things a bit differently. So, like a lot of B2B SaaS companies, big sales teams going out, direct to customer kind of selling, and they're leaning so heavily on their brand. And I think what he said, it was so interesting about the idea that, if you're going to compete on features you're not going to win. Everyone's got the same features. But you have to build that brand that people are going to fall in love with. They're going to fall in love with your story, and those are the people who are going to want to do business with you.

Christian: I think when he said that comment about good product will sell itself, I had the same sort of skepticism, think well I don't know if that's true. But I think what he meant was not that if you just make a good product and you just put it on the internet and everybody's just going to buy it. It was more that good product will sell itself. Meaning look at the product, all the things that you need to sell this and market this should be reflected in the product.

Christian: And one of the things that I think a lot of B2B companies struggle with, and I think it's kind of old school mentality, is we build features and products for large customers. We even- [crosstalk 00:25:02]

Anna: But that's how a lot of this offer in this town was built, right? It was vaporware. And they built it to the first couple of people who would buy software.

Christian: Large contract driven, and then over time you keep building these. And you make good money that way but eventually your product becomes kind of unstable and unsustainable.

Anna: [crosstalk 00:25:18].

Christian: So they have the six pillars driving the product. So, it's not as if they'll just do anything in the product to kind of customize it for a new client. It still has to roll up into something larger. Which makes it a lot easier for them to tell their story through the product. Whereas a lot of B2B companies, if you continue to create customizations for clients over time, you're left after a few years with something that just doesn't look like anything.

Anna: We didn't get much into this with him. But the way that the product marketing and the product management sides of the house are so integrated, and the idea that when customer requests come in the, they kind of bucket them into, the buckets are ready, and they fall into a pillar. Of, what pillar of Do Better Work does this request fall into? And then of course what team builds it, because each team is responsible for a different pillar. And I think that probably is another way maybe they keep from doing that such deep customization, is they have their roadmap themes preset in a way.

Christian: Right. And, he mentioned switching over to sort of Agile marketing, which you hear more and more about, but still not a lot of people practice it. That allows his team to be just as flexible. Like when he joked about not having a strategy, I think it was joke. I don't know, he might be serious. But he seems to be succeeding, so if he doesn't have a strategy, then maybe this is a new way of doing things.

Anna: And he had this great quote, they're concerned about what's true right now, and then they adapt as things change. Which I think, is a general [inaudible 00:26:38].

Christian: Mm-hmm (affirmative).

Anna: I mean, we can all take and apply.

Christian: So the B2C, I can't remember if we talked about it or if we were talking about it afterwards, about there's this idea that in the B2B world everybody has to talk like in features and capabilities, and it's almost as if, if you were to personify a brand voice for B2B, it's like somebody's wearing a suit. Or a power suit, or whatever they call it. That's almost like the traditional logic, I guess, if a tradition existed in B2B.

Anna: Like, professional trust.

Christian: But now, Lessonly's taken, and it's not unprofessional, but it's very personable, it's very direct, what they're talking about. Yellowship is almost charitable in what they're trying to do for people and it all comes through. So they're creating a brand that, I think we would see with B2C. When you think about, I don't know, Casper mattresses, or a lot of this Warby Parker, a lot of this space getting taken over by brands that are speaking directly to consumers.

Anna: Yeah. And I think another good example of kind of similar to what they're doing is Mailchimp. I mean Mailchimp has a really playful, fun brand, and it's a B2B product. I think people can use it.

Christian: Email marketing is also highly competitive. And it's really well established, so the only way Mailchimp's really been able to succeed is through a strong brand and a brand voice coming through. And I think Lessonly is probably ahead of the curve in their industry. We don't know all the competitors there, but I would venture to say that, there's nothing wrong with establishing that brand now, because ultimately over time, and we see with technology it moves so fast, that you have to find something that actually competes when everybody's doing the same thing.

Anna: That's what Kyle said, right? If you go to feature-feature comparison with them, you might lose. But if they love you and if they love your brand, then they'll want to do business with you.

Anna: Thanks so much for listening to the show this week. If you haven't yet, be sure to subscribe, rate, and review this podcast. Until then, visit [ 00:28:35] and subscribe to learn how you could take your product to the next level.

Anna: As always we're curious, what does better product mean to you? Hit us up at Twitter @innovatemap, or shoot us an email at

Christian: I'm Christian.

Anna: And I'm Anna. And you've been listening to Better Product.

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