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This week on How To Win: Kyle Lacy, Chief Marketing Officer at Jellyfish and former CMO at Lessonly, a sales training and coaching platform. Lessonly was acquired by Seismic in 2021. Kyle also served as the Director of Global Content Marketing at Salesforce after its acquisition of ExactTarget in 2014. Before its acquisition, Lessonly made $24M in revenue and had a team of 230 that migrated over to Seismic. Lessonly was used by 1,200 B2B customers.
In this episode, Kyle breaks down six important lessons he’s learned throughout his career. We discuss making the customer the hero, why you should always be willing to experiment and take risks, and why you should encourage your teams to grow their relationships. I give my thoughts on the power of customer feedback, building a strong brand moat, and trusting your team to be creative.
Hear how successful B2B SaaS companies and agencies compete - and win - in highly saturated categories. No fluff. No filler. Just strategies and tactics from founders, executives, and marketers. Learn about building moats, growing audiences, scaling businesses, and differentiating from the competition. New guests every week. Hosted by Peep Laja, founder at Wynter, Speero, CXL.
Six tips for building your business with Jellyfish's Kyle Lacy
Kyle Lacy:
Generate revenue first as a marketing team and then support that with doing cool grand investments.
Peep Laja:
I'm Peep Laja, I don't do fluff, I don't do filler, I don't do emojis. What I do is study winners and B2B SaaS, because I want to know how much is strategy? How much is luck? And how do they win? This week, Kyle Lacy, CMO at Jellyfish. This guy, he has a wealth of knowledge. Previously he was a SVP of marketing at Seismic, CMO at Lessonly, running marketing at OpenView, doing content marketing in Salesforce and ExactTarget, basically he has a ton of experience, lots of lessons learned.
Today's episode of How to Win is going to be a little different. In this episode Kyle breaks down six important lessons he's learned throughout his career. We discuss making the customer the hero, why you should always be willing to experiment and take risks, and why you should encourage your teams to grow their relationships. Let's get into it.
So why don't you kick it off with lesson number one, a meaningful story.
Kyle Lacy:
A meaningful story scales culture and community. My favorite quote ever is from Ben Horowitz, which is, "The company's story is the company's strategy." You and I both know in the marketing world the story is everything. I think where marketers lose is when they focus so much on only the external story of the company and not both the internal story, the employees, as well as the external story of what the company is selling, what's the product offering?
I believe that a great story will do two things, it will help scale your culture, and especially, I know you and I could talk for hours about VC-backed back companies, but in VC-backed companies, you're scaling much faster, you're hiring hundreds of people in a quarter, or a month, or whatever, no matter how big the company is, it helps you scale culture if you understand the story and how you onboard employees appropriately.
So at Lessonly, our mission statement was, "We help people do better work so they can live better lives," and do better work was our storyline. It was our external messaging, because we had a training and sales coaching product, we helped sales reps do better work, but it was also our internal story as a company that we help our employees do their best work, and then we had our values, and all that stuff. So what I learned at Lessonly was, by codifying those values and that messaging, it created a stronger culture internally and externally with our customers in the market. So number one, a great story scales interlynal and exterlynal.
Peep Laja:
You also have said that story helps you win competitive deals. How so?
Kyle Lacy:
If you tell the story the right way, the Lessonly story is that we wrote a book called Do Better Work, it was by our CEO.,It was about the leadership values of Lessonly, and what happened was our prospects were buying the book, and Max was going and speaking to these leadership teams, as we were in the sales process. So if we were competing against a Trainual or a WorkRamp, none of that was happening on the competitive side. Max was in the room with these leaders despite the fact that we were in a sales cycle.
So it just helped in terms of relationship building with champions and buyers, and it was also different. We weren't giving a book that was like, here's the six steps to build a great sales training platform, it was, here's how you can become a better leader. So it was higher level, but I think because it was higher level it worked better because we weren't selling, we were just saying, this is how we think you should build a team, and by the way, Lessonly, our product, fits really well when it comes to leadership development and onboarding employees, and all that stuff.
Peep Laja:
As startups get bigger they realize that they need to communicate more in story, their narrative needs to be connected to a bigger concept and be a strategic narrative. The world used to be like this, but now it's changed, and our startup will help you in this new reality. Many dismissed strategic messaging, brand storytelling, and positioning as marketing fluff. What these companies fail to realize is that story is the strategy. Your brand and story can act as a rallying cry to your audiences. Writing their book allowed Lessonly to communicate their story to customers in an impactful way , and indeed directly led to them acquiring more customers. So so-called marketing fluff can generate a lot of revenue.
You've also said that story plus category creation is even more win. How do those two things fit together?
Kyle Lacy:
A great example is Seismic, they have a great story to the market, but they also have built a category around sales enablement.
Peep Laja:
We had the CEO of Seismic, Doug Winter, explain how they created the category of enablement in a previous episode of How To Win.
Doug Winter:
And I think as you're defining a category, you really are, you're defining a category. Everyone has a picture in their head when you say words like enablement, over time those pictures have changed and I think a lot of our job has been over the years to educate the marketplace on our definition of what enablement really means. Working together with our customers and seeing where the value is added and where the pain comes from, and then working on solutions for those things, and then applying the terminology enablement and having it become popular.
Kyle Lacy:
I think it's more valuable when you can communicate to analysts about what you do, but also move people in a positive way to buy something outside of just, you need the best sales enablement platform in the world, like say something different.
Peep Laja:
What's Seismic's story then?
Kyle Lacy:
It's one platform to manage all enablement across the entire company, so it's not a bunch of different point solutions. They have brought on this idea, after the acquisition of Lessonly, of how do we help people manage content appropriately, manage onboarding appropriately, to help them do their best work? We combined it as the companies were connecting, but I think they've done a good job telling both stories. It's a different market too, because it's enterprise.
Peep Laja:
You've also said that a story will fail if the employees don't believe it, or if the customers don't believe it.
Kyle Lacy:
Similar categories. You and I can name 50 people that have tried to create 50 companies that have tried to create categories, there's thousands of categories out there, just go to G2, they're everywhere. When a customer is not saying it, it's not a category. When I joined Lessonly we had learning automation software. Nobody cared, nobody cared, and that's my problem. You and I could talk about category creation in general, because I think most of the time people are doing it wrong, and I learned that at Lessonly, but nobody cared because nobody was talking about learning automation, they were just talking about the product benefits, like what are the benefits that it's giving me? I don't care if Forrester has a NOW Tech coming out, or whatever. But it's a fine line and it's hard to do.
Peep Laja:
Your next lesson is about making customers your heroes. So how do you do that?
Kyle Lacy:
It's pretty simple. Great companies are building partnership with great customers. I am tired of going to websites and not seeing a customer's face, just seeing air quotes, not putting them at the center of the marketing, trying to figure out who the customers are. I also think that marketing leaders, and a lot of leaders in general, aren't spending enough time talking to customers, which blows my mind. I had to learn that pretty quickly. But if you're going to do a campaign, put the customer at the center of the campaign. At Seismic we rolled out an out-of-home campaign where we put our customers on the billboards, we put our customers talking about what they do best. Now of course Seismic is on it, Seismic was the sponsor of it, but we wanted to celebrate the customer instead of saying, "Seismic's the number one platform for sales enablement."
It's like, hey, let's have Nicole from Citrix talk about how she leads enablement, and Seismic's just the supporting platform for it. Marketo did it brilliantly in the past, I think it was called 50 Fearless, or the Fearless Marketers, or something, where they had huge banners of people hanging at their conference, and it was like they were celebrities, these 50 CMOs, and I've always loved that. So make the customer heroes, just putting them at the center of marketing, and even just doing something simple like start a freaking customer advisory board, talk to your customer. I don't know if you see this very often, and I'm sure you do, but marketers don't spend enough time talking to the customer base, which is crazy.
Peep Laja:
Talking to your customers unlocks growth. When you look around, the winners are paying attention to customer needs and adapting their marketing accordingly. Customer feedback is a superpower, you need to know, what do your customers want? What do they think? The words on your website, in your ads, whatever, are they hitting home? Are the people nodding their heads? And if you don't know what they're thinking, you might be sending out irrelevant messages that nobody cares about for years. If you don't know the customer, that's a problem. Here's Red Hat's Claire Delandy talking about the techniques they use to get to know their customers.
Claire Delandy:
You have, I would say, the old traditional way of doing surveys, focus groups. We use a lot of communities within Red Hat as well, we have a developer community, we have some tech community, so we try as much as we can to speak to customers and potential customers to reflect on what's going on. We are looking as well to work with a lot of different partners who are feeding us as well with some feedback, so we are not just alone selling to customers, we have a broader ecosystem supporting us. So I think we are trying as much as we can to get some insights from different perspectives. We're talking, as well, a lot to influencers, analysts, and the media as well is helping us as well to better understand the trends and how to capture really the market trends.
Peep Laja:
Your third lesson is about revenue versus brand, or rather revenue first, brand second.
Kyle Lacy:
I believe that brand marketers have the hardest job in the world because it's really, really hard to justify spend. It's really, really hard to talk about why you should spend X amount of money, without using attribution models or share a voice, or whatever the hell metric you can come up with, NPS scores. I believe that marketing should be revenue generating revenue or pipeline first, and then making the brand investments once they've figured out the revenue side. Revenue gives you a seat at the table as a marketing leader. If you think about budgets, it usually breaks down 60% should be demand gen, 20 or 30% should be brand spend, and then 10 to 15 is operations. But that 60% is your most important.
So at Lessonly we were spending 60 to 70% on generating inbound revenue, and then the 20 to 30% that we spent on brand was less important to the board because we were hitting our revenue numbers. We did a Lego llama, we did a board game, we did events, tons of digital events, and as long as our efficiency number stayed with what the board wanted across sales and marketing, they never questioned the brand side. And I would argue that the brand played huge in our acquisition, and the multiple we got on the acquisition, because we had something that was valuable when it came to just the brand.
Now people love talking about branding, they don't love resourcing branding. Boards, investors are like, "Brand's the best thing," but then when you get in the weeds it's like, "You want to spend a hundred grand on out-of-home? You want to spend it on billboards?" And yeah, maybe you should, because nobody else is doing it. Maybe you should do direct mail instead of a ton of money in LinkedIn ads. Generate revenue first as a marketing team, and then support that with doing cool grand investments.
Peep Laja:
Every marketer needs to also be a brand marketer, know how to work with it. 95% of the market is not actively looking for you, and won't buy for months, or even years. So what do you do? Give up? Focus on the 5% who are in market today? Ignore the 95% who aren't? No. Marketers should focus on the 95%, the out of market buyers, and the right approach here is brand marketing. A strong brand is your moat, a reason to choose you, a way to resonate with the buyer. You need both, revenue marketing to push sales today, as well as brand marketing, cultivating the buyers of tomorrow.
Lesson number four is building on this brand thing, be experiential and irrational.
Kyle Lacy:
Rory Sutherland, he wrote a book called Alchemy, I read that book and I was like, hell yeah, because it explained the way that I think as a marketer, which is, and I'm just going to read a quote to explain it, we can get in the weeds on stuff that we've done, but, "It is much easier to be fired for being illogical than it is for being unimaginative, the fatal issue is that logic always gets you exactly the same place as your competitors." Marketing without allowing your team to be a little bit irrational, you're never as creative as you can be.
So for brand campaigns, as an example, we never put a revenue number or a pipeline generation number on a brand campaign because I didn't want the creative team to be stuck thinking about a pipeline number, I wanted them to be as creative as possible, because our competitor was not going to say, "We need to send a golden llama to people through direct mail." They were never going to do that, or they were never going to design a board game, and I believe that that differentiated us as a company because it was the experience. And ultimately as marketers the only thing that makes us relevant is the experience we're creating for the prospect of the customer. That's it, that's our relevance level. So if you can create some irrationality, it helps with the creativity of the team, and all that stuff. That's why we launched clothing lines at Lessonly, at Seismic, and it makes things more fun too. New ideas differentiate brands and they create memorable experiences.
Peep Laja:
Some business problems you have might be logic proof, and irrationality is exactly what's needed. Here's Rory Sutherland explaining it.
Rory Sutherland:
If there were already a logical answer we would've already found it. Now this isn't the Middle Ages, there isn't a shortage of people who are desperately trying to look logical to each other. You can call them McKinsey, you can call them your board of directors, you can call them your finance department, you can call them your procurement department, rational people are all over the sodding place and they control everything. Therefore, if a problem is persistent, it's fairly likely, I would suggest, that the reason for the persistence of that problem is that it's logic proof. There may be a solution to it, but conventional linear rationality isn't going to find it.
And so little while ago, I totally hate things that aren't dishwasher proof, so I said to my wife, "Look, here's a suggestion. For two years we'll treat everything in the kitchen as if it's dishwasher proof, and by a process of Darwinian elimination, two years down the line everything that survives, by definition, will be." Now in the same way, if you expose everything to logic and the things still persists as a problem, it's fairly reasonable to assume that logic isn't the answer to that particular problem. So the problems that persist, the problems that the bedevil government decision making, the problems that divide politicians, the problems that obsess businesses, are probably still problems because no one's yet had the balls to try an irrational solution to them.
Kyle Lacy:
Hiring creative people and giving them space to think. Usually what happens is that you set a bunch of creative people in the room and you're like, "Let's run a post-it note thing where we put ideas on the board and everybody chooses what their favorite thing is." Just give them space, you don't have to be in the room. Say, "There's not any guidelines, just go think about the most creative thing possible," and that's where we got some of our creative ideas, and I had to be irrational enough as a leader to say, "Go do it, I love it."
Peep Laja:
For assembly line type of work, create all the standard operating procedures you need. For creative people to do creative work, you need to give lots of room for independent judgment. Sure, you need guardrails, but jobs should not be decision trees in a document.
to Your next lesson is encourage alignment through shared goals.
Kyle Lacy:
I think Udi from Gong says this, which is, "You should know your sales leader's coffee order." I think that's a direct quote from him. Alignment between all business units is very important no matter what size and scale, and for me, marketing should own OKRs with sales. That's pretty much the extent of the lesson. Where people get siloed is when marketing's off doing whatever the hell they want, and sales is off trying to hit a quota, and nobody's talking because they don't, that's why marketing should own a revenue number, marketing should be responsible for some percentage of a rep's quota, then you're forcing alignment. I also think that you could have BDRs report into marketing as well if you have an outbound motion, I think that also forces alignment, but shared goals is the most important thing.
Peep Laja:
What is the north star metric for marketing?
Kyle Lacy:
I think it depends on the business. Lessonly was high velocity, half of our deals closed in quarter. We had a closed one revenue number because our inbound motion was so strong. Seismic, enterprise level, huge sales cycles, huge deals, it was a total pipeline number. But also you can do an inbound pipeline number as well, inbound sourced pipeline. So I think it depends on the business model, but it should have a number, this shouldn't be like marketing's a production org. When you're a production org, you're just one sheets and decks everywhere, you're going to get your team cut in half, budget's going to be taken from you, your leader's not going to have a seat to table. So having that own revenue number helps align sales, marketing, and CS, if marketing's also involved in net revenue retention, or net dollar retention. And that gives even more support from a marketing side, and a lot of times marketers don't think about what happens after the deals close, which I think is a loss.
Peep Laja:
You've also said that the glue that holds everything together is rev ops, revenue operations.
Kyle Lacy:
It's something I came across, Seismic I think built it appropriately, their biz ops leader lives on the exec team. When it's a smaller company, like a Lessonly, biz ops, sales ops, marketing ops lived in the CFO, under the CFO. Sometimes they live in the teams, like you have marketing ops, sales ops, CS. I believe that it's a separate team, they're the people that should be running the pipeline forecast meetings, they should be running the revenue meetings, they should be running the reporting, because they are the people that keep revenue teams accountable, not marketing and sales arguing.
Peep Laja:
What about meeting cadences to bring all the stakeholder, sales, and marketing together? How often should they meet and what should they talk about?-
Kyle Lacy:
Revenue-generating teams should be meeting weekly. There's a pipeline of forecast meeting where you're saying, what happened last week? What's going to happen next week? Your inbound leader's given a called shot, your outbound leader's doing a called shot, your sales leader knows how much dollars is going to move into closed one, or move to the next stage of the sales cycle, and the operations team is keeping people accountable. And then I think it's up to the business unit leaders to be meeting weekly. I don't understand how you can grow a business or do business where the sales leader and the marketing leaders meeting once a month. Just seems crazy to me. Y'all should be tied at the hip constantly, because you have to be, you're moving so fast, and if you want to be competitive, you want to be able to move as quickly as possible and the only way to do that is through alignment. It doesn't have to be really long meetings, but you should be touching base, for sure.
Peep Laja:
And where does product marketing fit in here?
Kyle Lacy:
My number one failure, man, not hiring product marketing soon enough at Lessonly. I think product marketing, I think that forces the alignment with the product team, in my opinion, for every product manager you're hiring a product marketer, but I also think they help with just the enablement. You could argue that sales enablement should live in enablement, I also think that it works pretty well within product marketing, where you are constantly enabling and training and coaching the customer facing teams on the changes in the market, the persona challenges, what the hell's product doing on the roadmap? That type of stuff.
I think that they could also be seen as a hub. At Lessonly, our product marketing org lived within sales enablement, which is fairly, actually is very odd, you don't see that happen very often, because they were the hub with all the different revenue folk. So product marketing, I think, is essential to just understanding the market in general, and without that it's just really hard to make decisions on how to position a product, or pricing of a product, the competitive landscape, win, loss, all that stuff.
Peep Laja:
Product marketing as a function is still unfamiliar and confusing to many, and even some product marketers can't define it well. The best way to think about it, product marketing is strategy, it's basically the same thing, and we need to start explaining it that way. Product marketers work to understand the market and customers. They choose the market segments to target, determine what attributes the product needs to win against the competition, design an effective good market plan, along with the required positioning and messaging.
Your sixth and final lesson is invest in your team's career.
Kyle Lacy:
Your job as a leader is that the people on your team should never have to use their resume to get their next job. You should be talking to them about network development, you should be talking to them about talking to their peers in other companies. I hate the term networking, but you know what I mean, building a community of people around them to where they are poached from you, not we failed and they have to go find something. You as a leader should be training them for their next thing, and if their next thing is not at the company that you're at, you should be fine with that and you should be excited. Because life's short, life's even shorter in venture back software, but that's what I tell every team I manage, it's more about your career than it is the job you have right now.
Peep Laja:
And in very practical terms then, what do you do? How do you ensure that as a manager?
Kyle Lacy:
It is how many meetings are they having on a quarterly basis with their peer group? You need to do two a month. "Hey, demand gen manager, I would love for you to meet with two other demand gen managers, and I'd love to know what you talked about." That came very naturally to me because my father taught me that early on. I hated it when we talked about it in high school, but he taught me it, and it just does not come naturally to people to say, oh, I should go talk to my peers. They're so focused on their day-to-day that they don't think about what you could learn. This is why we do podcasts, this is why we listen to podcasts, when I'm really, really stuck on something I'm going to send Udi a note through LinkedIn, because that's what makes the job fun. But yeah, I would have it as a personal OKR for your teams, is that they have to meet peers.
Peep Laja:
Personal relationships open most of the doors, from business deals, to Stanford graduate program entrances, to raising VC money. Relationships get you back links, conference speaking slots, and word of mouth. Basically, the good old nepotist is well and alive. No matter your goals, relationships is the rocket ship to get you there. As the saying goes, context become contracts, and your network is your net worth. Here's Verhaal Brand Design's Philip VanDusen explaining the benefits of strong business relationships.
Philip VanDusen:
Building relationships and establishing trust over time is probably the most important thing that you can too for your business, and it's also the most important thing and the best way to build your network. It's all about giving value to others, and hopefully in time getting value from them. So getting people to the point where they really look forward to hearing from you and look forward to opening your emails is valuable because eventually when you ask for that favor, you ask for that referral, you ask for that introduction, they're going to be more apt to give it to you. You may be looking for a job referral, or you may be looking for a client introduction, or some sort of LinkedIn introduction, or something like that. So when you ask for that favor, they are more likely to say yes. Essentially what you've done is you've built up equity with them, you've built up relationship equity.
Peep Laja:
In addition to these six core lessons, you've had some other interesting thoughts that I would love your take on. One is budget size doesn't matter, it's about moving quickly.
Kyle Lacy:
What I've found with moving into a larger org, when we moved from Lessonly to Seismic, where my budget was basically 10x what I had a Lessonly, the tactics that we were employing didn't change at all, it was just the size, it was just the size of what we were spending. So for me, I thought that, hey, with the larger budgets, you're still doing a ton of testing, you're still trying to figure out the most optimal way to spend this money, it just doesn't change. It does not matter whether you have 1 million in programs spent or 10 million in programs spent, or 100 million in programs spent, you're still doing the same type of tactical things as a team, or you should be. When you don't, then you've got an issue.
Peep Laja:
What are Kyle's top three winning lessons? One, make your company story your strategy.
Kyle Lacy:
Do better work with our storyline. So what I learned at Lessonly was by codifying that messaging, it created a stronger culture internally and externally with our customers.
Peep Laja:
Two, when approaching your marketing, speak to your customers.
Kyle Lacy:
Great companies are building partnerships with great customers.
Peep Laja:
And three, build a culture that encourages relationship development.
Kyle Lacy:
Your job as a leader is that the people on your team should never have to use their resume to get their next job.
Peep Laja:
One last takeaway from Kyle.
Kyle Lacy:
You're moving so fast, and if you want to be competitive, you want to be able to move as quickly as possible, and the only way to do that is through alignment.
Peep Laja:
That's how you win. I'm Peep Laja, for more tips on how to win follow me on LinkedIn or Twitter. Thanks for listening.