The First 100 Days as a First-Time CMO with Kyle Lacy, Lessonly

‍Kyle Lacy: [00:00:00] If you're building out an attribution model with your team in the first a hundred days, you are doing your job incorrectly.

Trinity Nguyen: [00:00:09] Welcome to the first 100 days. A show for revenue practitioners in five revenue practitioners, giving you unscripted access and exclusive resources to help you navigate any new transition or initiative I'm Trinity Nguyen. And I'm your host for this episode. For our very first episode, I could not have been more stoked to be interviewing our guests.

If you’re in SaaS  and you're in a revenue role like me, you probably have heard of Kyle Lacy. Kyle is well-known throughout the revenue community, and he's a thought leader in the marketing space. He's currently a CMO at Lessonly, a training software company based in Indianapolis.

Two years ago, Kyle became a first-time CMO. 

So I invited him onto the show to share his journey, his learnings, and his cheat sheet, going from being a VP of marketing to a first time CMO. 

Side note, outside of work, he's a chapter head for revenue collective. He also hosts a podcast called “Revenue Diaries”, where he interviews all the revenue leaders about everything other than work.

I actually really enjoy Revenue Diaries. Fun fact, it’s in my top five Spotify podcast for 2020. So needless to say, I'd encourage everyone to check it out. 

All right. Let's talk about the first 100 days of being a first time CMO with Kyle Lacy. 

Trinity Nguyen: Kyle, as you know, we’re focusing on the first 100 days of any new transitions or a new initiative, and that new transition for you was a promotion from being a VP of marketing to becoming a first-time CMO.

So before we get into the details, I want the audience to get to know you a little bit. So can you give us a speed dating version of your impressive career? 

Kyle Lacy: [00:02:02] I was doing content marketing and thought leadership stuff at ExactTarget. Fell in love with SaaS, that ExactTarget understood what huge SaaS companies, how they interact with the world at Salesforce.

I got an MBA in SaaS at OpenView and Lessonly is an OpenView portfolio company. So when I realized that venture capital was not the route I wanted to take as a partner in my career in general, I wanted to get back into an operator role. And Lessonly was looking for a VP of Marketing. And it just made sense.

So most of it's been content marketing strategy and growth. 

Trinity Nguyen: [00:02:39] In one of your recent episodes in Revenue Diaries, where you interviewed Sam Jacobs, you asked this one question and the moment I heard it, I had to pause, rewind because my jaw dropped. So I'm going to flip the situation and ask you that question, I don't know if you know which one's coming. In the book Selfish Gene that you mentioned where Richard Dawson says: “You can make some inferences about man or woman's character, if you know something about the conditions in which he or she has survived and prosper. So I'm going to ask you, what are the conditions you have survived, any challenges you have overcome so far that made you the person you are today? 

Kyle Lacy: [00:03:18] I think for me, it's two fold. One is overcoming and learning how to deal with self-confidence issues. Some people call it imposter syndrome. I have learned to compartmentalize that and use it to grow instead of it being detrimental, even though sometimes it can be, I've spent a lot of time working on the confidence and making sure that it's real confidence and not fake confidence, because you can definitely tell when somebody is trying to fake a confidence level. And you know, I've spent a lot of time trying to understand where that comes from. For me, it’s “how do I keep striving for a better job or a better confidence or growth in general”? Like, betterment of me, without it being detrimental to relationships and stuff. Cause I think sometimes people can, because they have imposter syndrome, they work extremely hard to try to overcome it. And they ruin relationships in the meantime. And for me, a lot of my self-worth is built in my career pretty much 60%, 40% of my kids and wife. Right. But some people are probably cringing listening to that, that a lot of my self worth is built in my career. But before kids and wife and family, a 100% of my self-worth was built in my career. So I've had to get over that. And I think that's really shaped me.

The other thing is just growing up in a conservative religious household, evangelical household in Indiana and how I've dealt with my own faith and moving in, in and out of atheism, if you can actually do that. But those two things have shaped me for who I am today, for sure.

Trinity Nguyen: [00:04:51] I feel like the imposter syndrome is actually more prevalent than people make it sound to be. But I think the culture here doesn't encourage people to be vulnerable. So I think you've talked about this in one of the other episodes in your revenue diaries as well, but imposter syndrome, the VP of marketing of Terminus, had to watch Youtube to learn how to use Salesforce. We all try to improve ourselves, but like that voice inside your head, if you can share it at some points, I would love to know what you did. 

Kyle Lacy: [00:05:25] It's quick. It's simple for me. It is. How do you channel the imposter syndrome to get better at what you do?

Not let it be detrimental. You know, for me, it's just making sure that I am working hard and I'm working to better myself every day and being empathetic with myself. Right. We talk a lot about just empathy for other people. Well guess what? You're, you've got to have empathy for yourself, cause you're not going to succeed all the time.

You're going to fail. You're going to fail miserably sometimes because we're all human. And I think I had to develop the empathy for myself and how I dealt with things in order to really deal with it because I will never overcome it because I believe that if you channel imposter syndrome the right way, it can be a superpower because you're always striving.

Trying to prove something to yourself. When in reality, I'm never going to be able to prove it, but I'm just going to still keep trying

Trinity Nguyen: [00:06:18] You've been in marketing for years. And you know, and you've seen a lot of executives usually externally hired into the roles. And in the first few weeks advice I usually give is to understand the needs of the new peers, the team, the board, et cetera. But yours was an internal promotion at Lessonly. And I'd love to just pick your brain on how did the roles differ? How do the roles differ? Like how did the expectations from the leadership and your team change? 

Kyle Lacy: [00:06:48] They didn't really, honestly, you know, when I walked into Lessonly, the VP of marketing role was on the exec team and, you know, the responsibilities changed because we brought the business development reps, BDRs and SDRs under marketing in 2018 at Lessonly.

And then I, and then I moved up into the CMO position, but there wasn't a, there wasn't really a discussion of like, here's what you need to do in order to get the COO role. I think that is partly because it's Lessonly and we do things a little bit differently just by the way, we're run as a company. But for me it was.

Mostly just the title adjustment, honestly. And it's something that I it's one of the goals that I had had for myself, not necessarily at Lessonly, but you know, to be as CMO before I turned 35 and I got it right at 35. 

Trinity Nguyen: [00:07:44] So even though there wasn't exactly a change of expectations from the leadership. But now as a CMO, you’re hiring your team, like other VP of marketing and head of marketing, you probably see the difference in terms of roles, right? So some other people who are VPs right now who need to make a case for their promotion, how would you say the roles differ between a VP and a C-suite.

Kyle Lacy: [00:08:09] I think it's mostly on how far ahead you are planning and this is not a perfect, this is not a perfect model. I am terrible at this in my current role. And my team knows this, and this is something I need to work on. But if you're a CMO, you should be thinking 12 to 18 months in advance. If you're a VP, you should be thinking eight to 12. If you're senior director, you should be thinking to two quarters in advance or director or whatever.

And then if you're a manager, you're probably a frontline manager. So you have quarterly, you know, you're thinking on a quarterly basis. I think that's the biggest leap you have to make is, is the strategic thinking around the future of the team and the company, depending on what role you're in, you know, marketing, what does messaging look like for Lessonly a year from now?

And if my team members are listening to this, which they probably will. They know that we're not great at that right now. And we're trying to fix that, but it's “how do you proactively think”, I think is the difference between a VP of a CMO. And I would say that I did adjust that, or I had to, um, and it also helps, you know, when you hire in people who do it as well in the VP director level, senior director level.

Trinity Nguyen: [00:09:17] You mentioned you had to adjust for that, can you share a little bit more detail? How did you realize that adjustment yourself? How long did it take you to realize it and how do you actually execute that adjustment?

Kyle Lacy: [00:09:28] I think it's an evolution of a company. I joined Lessonly at 50 people. We'll finish the year at 200. As you adjust and add more people, there are layers that you have to put on in the strategic process.

You need alignment with sales alignment, with CX alignment, with sales, engineers, solutions, consultants, like the level of complexity of the org kind of pushes. Leaders to think more strategically you have to, or you will, or you will burn out you'll churn out of the company cause you can't keep up with it. Right. 

So for me, I had to do it for me between the first two years at Lessonly to the last two years of less than only the first two years I was in the weeds quite a bit. And these last two years have been more executive level projects. Like working with Forrester or owning a go-to-market strategy for enterprise for the next two years.

And not necessarily like helping manage nurture tracks and Marketo, or giving feedback on a landing page. Like, I don't give feedback on a lot of that stuff anymore. So delegation, sometimes it's a hard skill to learn. 

So it was really my managers that helped with that. Our director of marketing at the time, Ben Bataglia who went on to be a VP at a startup here at Indy. He developed a system called squads. So they're basically committees of marketing team members. So BDRs, graphic designers, web dev, whoever, and they were responsible for projects. And you had a project owner and that project owner owned the project plan. So, if we're doing a campaign, they are the point person for that.

All that stuff feeds into Monday.com. And we talk about it an hour each week. So because we had those squads and because I had inherited and hired managers that were really good at building processes. So that speaks to your ability to delegate is based off of your ability to hire people that balance you. Right? 

Because I am terrible at process development, like horrible. It’s not a natural skillset of mine at all. My team knows that. So it's just hiring people that have different skillsets and trusting those people to get the job done well.

Trinity Nguyen: [00:12:00] One of your LinkedIn posts about one of the priorities that you had in your first 100 days as a CMO is to produce and share customer success stories at the very beginning of a product's life. So, was bringing in a product marketing and customer marketing the new priority? and why did it come to your priority list as a CMO and not when you were VP of marketing?

Kyle Lacy: [00:12:25] I actually listed that on that LinkedIn post because those two things I should have done as a VP of marketing. So I had the ability within the first year to hire on a product marketer and I decided to readjust the headcount to hire somebody else, a different role. And that person's still at the company and they're excelling, and it's awesome that we hired them. But we should have hired a product marketer because what happened was, as the company grew business outcomes, commercial insights, like data behind what the success that the customer was having with Lessonly was not being captured in a way that was meaningful, or it could be used.

And now we are doing that. But the reason why I put that is because in my mind, for product led growth or sales led, it doesn't matter. You’re either hiring a product marketer in your first a hundred days, or you're hiring a really good graphic designer. And those are the two, in my opinion.

I was lucky that when I joined Lessonly, there was a great designer already. There was a great content, PR, we had a good team. But if I were to go into another role and they didn't have those two things, they would be my first thing. 

Trinity Nguyen: [00:13:39] So it's interesting that you said that they did have customer success stories, but the data behind the success of the customers weren't shared in a meaningful way, can you clarify what that means? Like, what would a meaningful customer success stories look like? 

Kyle Lacy: [00:13:53] Yeah, well, I mean,  it's mostly just setting it up, sending the agreement upfront with the customer “Hey, here's the success metrics we're going to start tracking and tracking them across the entire life cycle of the customer”.

We have the, I would argue, you might argue this, but one of the best account managers in the country. In my opinion, our support system, after somebody becomes a customer is world-class. There is zero chance competitors that can touch our support system after somebody becomes a customer. So I want to make that very clear. But there's things like when we cut onboarding down for a customer from eight weeks to two weeks... the eight weeks to two weeks is important and we capture that and we use it. But what was the impact? Because it was cut down by 60% because we did, we saved millions of dollars capturing the commercial insight. And the business outcome was not something that we were funneling. So, like our customer success and customer stories on the website, if you go look, they are beautifully written, the narrative is amazing, but there are cases where we are just missing that commercial insight.

And so we have righted that now, but that's, you know, in the first a hundred days, I wish that that would have been something that I focused on. And I didn't, because product marketing is not a strong suit of mine. Like it's just not in my tool set. No, I think that's a challenge for a lot of companies.

We talk a lot about sales and marketing alignment, but marketing customer success alignment is almost just as important. And I could, I could talk about that for hours, but so we talked about delegation before. That's an example of where I screwed up and my first a hundred days, in my opinion, because product marketing is not a skill set of mine.

I should have hired somebody that balanced that. And I didn't. 

Trinity Nguyen: So what were the priorities in your first 100 days? 

Kyle Lacy: So my first a hundred days, actually 30 of those days, I just sat in the office and observed. So I spent the first month of my role at Lessonly as a VP of marketing, just going to meetings and not giving any feedback, basically just observing what the team, I think, I think you've mentioned this before, right?

Like meeting people, observing, taking in before you give feedback. I think leaders should do that anyway. And that's something else that I have to work on as a leader. So I spent the first 30 days doing that and then the next 60 days was just trying to prioritize exactly what we thought we needed to do.

To be successful as a team moving forward. So at the three where we overhauled the way that we reported the funnel way too many definitions lead visitor. We were just tracking way too many metrics. So we just cut them down to only four or five. That was the first thing was a better alignment between sales and marketing and on what, what we were doing.

And the second thing was agile. We tried to put an agile marketing play in place to manage the team. So daily stand ups, we started doing the Trello boards. Like portions of scrum. It was definitely a marketing version of agile. So somebody is going to listen to this, that's it actual scrum master, like, like I used to be and be like, this has nothing to do with that job, but it was just focusing the team, um, and making sure that everybody was following the same path.

And the third thing was putting together a funnel and forecast meeting between sales, marketing, and CX that happened every week. And the second thing was putting an exact meeting together where we were meeting constantly. 

Trinity Nguyen: [00:17:31] I did read a, your, one of your blog posts on your website about redoing the funnel, and you got the help from the folks at OpenView to redo the funnel. So if someone is joining a company and needs to redo that funnel and don't have the luxury of the OpenView team, how would you advise them to tackle that? 

Kyle Lacy: [00:17:42] I mean, I don't care. You have to simplify. You have to first things first, you walk through your funnel and figure the four steps. The funnel that mattered at the time it was lead - MQL - demo - closed won.

So that week, and then, and then you watch those conversion rates to see if that makes sense. Right? So you simplify it and then you make sure sales knows what the hell you're talking about. Cause you could say MQL and they have no idea. And then why would you be talking about it in a weekly meeting then nobody has any idea what you're talking about.

So simplify the funnel, um, and then communicate it. And I just think marketers tend to be data crazy and just look at too much stuff. Like you could look at like attribution models as an example, like give me a break. Like I get it. We should all do it, but. Just simplify it. So everybody understands you can, you can do your wonky stuff in the background, but you don't need to put an attribution model on a deck to show the sales team.

Trinity Nguyen: [00:18:46] I totally agree with you. 

Kyle Lacy: [00:18:49] It's kind of the same thing as influence, like people throwing out the influence number. And my, I will never use influence ever as a marketing leader as a metric because marketing should be influencing 100% of everything. Right. And if you're not doing that, you're not doing marketing correctly at a software company.

So in the attribution model, I get it for some things, right? Like if you want to track the, from somebody going to a Facebook ad to a Google ad, to your website and then Bri targeted and then coming back and filling out a form so you can spend your money better. Great. I just don't need to know about it.

I think my point is, if you're, if we're talking about the first a hundred days, your team can use whatever tools they want to make the best decisions to hit the goal that you're putting in front of them, whatever model they're using. Great. You just don't need to be involved in, in the first a hundred days as a CFO.

If you're building out an attribution model with your team and the first 100 days, you are doing your job incorrectly, right. It's about setting vision and it's about making sure that there's alignment between teams. I feel like that is 80% of a CMOs job is to set vision and to enforce the alignment as much as you can.

Trinity Nguyen: [00:19:56] So on that alignment one. So you mentioned like the four or five steps in the funnel earlier. So you said that it was the step. So I'm assuming this, the funnel that you have now has changed where you don't have MQL anymore at Lessonly. If I understand correctly, 

Kyle Lacy: [00:20:13] We do, but it's not something that we track very often.

Cause we just have one, basically we have one form, that's a demo. Everything else is pretty much on gated. So we don't really need a marketing qualified lead. We still track it. Like my team still is attractive because the conversion rate between lead and MQL, it starts dropping there's something going on with a website that we have to look at.

But outside of that, it's pretty much just demo to pipe 

Trinity Nguyen: [00:20:38] A hundred percent. We're doing the same thing here. Your background's in content marketing and a lot of time content marketers. The success is measured by the gated form and how many form filled. What was that moment that you decided to engage all of that? What went on in your head that got you to do that? 

Kyle Lacy: [00:20:55] Yeah, so I built my career at ExactTarget off of form fills and influence pipe and numbers that I don't talk about it anymore. To be clear, we talked about that a lot at ExactTarget, but ExactTarget was 2000 employees, hundreds of millions in revenue, like just a completely different company for us.

It was. We noticed that the tracking of leads to, uh, SQLs to revenue basically was starting to drop on in 2018. For some reason, we had no idea why. And what we found was that our website was loading so slowly that Google was starting to basically rip apart our S our organic search. We were getting, we were on second pages instead of first because our site speed was just terrible.

And so I pulled, we pulled the entire team out of the office and put them in a remote location and we completely overhauled our entire site and like eight weeks. And during that process, we made the decision, why are we tracking all of this crap? It does not matter. Let's cut. So we cut. The MQL is down significantly because it was just demo and our revenue, our inbound revenue, 10 X, because the team was focused on people that wanted demos.

There was urgency. There's a sense of urgency, right? There is not a sense of urgency when somebody downloads your e-book. I don't, I don't care how, how much time you spend on the ebook. Like if you really want, if you created an ebook that people want to read, ungated. Let people read it because I don't, I don't care to hear, you know, I don't care to hear from an SDR.

Now there are cases where you spend a lot of money on something like a Forrester, total economic report or a, you do a paid webinar. There's some things that I will gait to test. Right. We will test whether or not it works most of the time. It doesn't work at all. So you've got to balance the content creation and thought leadership with lead gen, because I think it's very different. It's a different animal.

Trinity Nguyen: [00:22:53] So that kind of ties in with why you think marketing should be measured by the revenue, not none of the influence. So that's still uncommon for many companies and marketing leaders, just different. What would you advise other marketers or revenue leaders listening to embrace this approach?

And is there a cap? like we are in the mid market, right? Is there a limit to this approach where like, Oh, if it's enterprise like ExactTarget, this would not work?

Kyle Lacy: [00:23:19] No, the first, the first thing is measure, measure everything off direct source. What was the first touch point that sourced the deal and put a timeframe around it? Right? So for us, it's a 90 day shot clock, basically. You know, if there's no interaction with the contact of record in 90 days, you know, whatever touch point came after that is the direct source. Then. So, first step is agree with ops and finance or whoever you need to agree with that. We're going to start direct source. Where did the customer come in? Where did the prospect come in? And you get the credit for that? If you can set that up, you don't have to talk about influence anymore. And when you grow as a company, like we are, we've introduced pipeline as a measure, but we're still, it's still direct source.

So we need to source X amount of pipeline. We need to source X amount of revenue. We need to source the X amount of meetings.

Trinity Nguyen: [00:24:13] If you were to create a cheat sheet for a first time CMO, knowing what you know now, what would be on it when you mentioned this throughout the conversation, but if you going to visualize that...

Kyle Lacy: [00:24:25] yeah, I would say, uh, my entire cheat sheet would be: launch a marketing request form. That was one of the, that was one of the better things that I did in the first six months of my job at Lessonly because the team was being stretched from everywhere. Like a CX rep could walk in and say, Hey Zach, could you help me on this deck? And then, and then they would be like, time management goes out the window when you don't have a request for launch a request form. 

The second thing is time management, like a cheat sheet. It is, there's a certain point where this becomes hard to do, but time blocks. Block two time blocks a day, 60 to 90 minute blocks of time that allow you to do deep thinking work, like getting involved in something that you can think through because my days are filled with meetings as I'm sure yours are. I have to do that at night sometimes. But if you are a first-time marketing leader, time management is huge. If you can figure out how to do 180 minutes a day of thinking and work. Your success is it's going to be a rocket ship because you're just working. You're not just going in between meetings and trying to talk to people.

Okay. Then the third thing is just figuring out alignment, your peers and sales and CX and enablement and product. You need to be their best friend. In a professional sense. You don't have to be their best friend in personal, but you need to be friend with them. You need to understand what makes them tick. You know, we use predictive index at Lessonly, you've got disk, right? You've got a ton of different stuff, ETQ stuff, but just understanding how they tick and how they work.

Trinity Nguyen: [00:26:02] Do you think having the BDR team reporting to marketing helps with some of that alignment? 

Kyle Lacy: [00:26:07] Yes, that was part of the reason why we did it. I thought that, you know, there was things that I wanted to do with that team from a marketing perspective. But the number one reason was because marketing is responsible for sourcing 80% of revenue.

It forces sales to care. And not that they don't, marketers are just as bad. Like we, we complain about changing decks and using clip art. And they complain about us never understanding their jobs, right? Like that, that will always be there. But if you are responsible for putting food on the table, you have to work together.

Trinity Nguyen: [00:26:43] So the very last questions probably I saved the most serious question to the end. What are your thoughts on weighted blankets? 

Kyle Lacy: [00:26:50] Well, you know, I love weighted blankets. I should put that on tips. Your first a hundred days is CMO by way to blanket. You go to gravity blankets and use Kyle 15 and get 15% off at gravity blankets.

Trinity Nguyen: [00:27:04] Oh my God. Are you serious? 

Kyle Lacy: [00:27:08] Yeah. So all kidding aside, my wife bought me a weighted blanket for, I think father's day, maybe. And it has changed the way I sleep. It is unbelievable the difference. And if you want another super power outside of figuring out how to control your imposter syndrome, it's just getting good sleep. Because most people don't, right. And I freaking love weighted blankets. I will never stop talking about it.

‍

Trinity Nguyen: [00:27:37] That was Kyle Lacy, CMO of Lessonly next. Next, I sit down with Christian CEO of UserGems to break down the conversation. 

What are some things that you think are the big takeaways for our audience?

Christian Kletzl: [00:27:52] I think there are three things that stuck out and there is the alignment part. I think that makes sense. Like once you become an executive, you need to make sure that your own department delivers the goals of the organization and therefore is aligned with the other parts of the organization.

What I found very interesting is about delegation. Like where it's about. It's obviously now you're in a position where you need to delegate tasks and there are actually two things that, that you need to consider to actually to be good at delegating: A) You need to be good at hiring, and B) and this makes sense, like as to be an effective leader, you need to know what you're good at; we also need to know what you're not good at so that you can find people that compliment you and only then can you cover all the tasks that your organization need to do?

Trinity Nguyen: [00:28:45] I think it's an advice that I've heard before, but I think it's actually harder to do in real life because people tend to like those who are similar to them. So it's actually really not just that you understand, like you have a strong self-awareness of what you're good at and what you're not good at, and then find someone who helps you fill that gap, it’s the execution of it. When you’re sitting across someone who is very different from you, how can you make that rational choice of hiring someone that compliments you and might not, you might not have that natural rapport like you would with someone who's identical to you. 

Christian Kletzl: [00:29:19] Absolutely. Talking about this, comes back to, in a sense, that the part he talked about imposter syndrome and how to take care of it, which is by figuring out what you're good at.

So that instead of faking the confidence, you know, what you're good at so that you can draw the confidence in you need from the things that you're actually good at. 

Trinity Nguyen: [00:29:40] Yeah, no, that's great. Another piece that he talked about... it wasn't in his cheat sheet because I think it came naturally for him, but I thought that was really really interesting, and I would love to implement that within our own organization and within the marketing team is: agile marketing play. 

So I've heard of agile in the product management, more in the technical engineering side, but not within the marketing team. And I would love to be able to bring that into our organization so we make decisions faster, experiment faster and learn faster.

Christian Kletzl: [00:30:12] Yeah, I think it's part of a few topics of like the forward thinking that he applies to his marketing, where so many of the things that we currently hear being a trend like: marketing isn't measured by influencer but measured by revenue, that SDR is part of the marketing organization, that you don't gate content, do you work in an agile way, etc.

I think so many of the things are actually very much forward thinking and we can think about whether we should apply them to our organization. 

Trinity Nguyen: [00:30:44] Are you going to, through a major transition within your organization or your career? Do you have a first 100 day journey to share.. recently or in the past? If, yes, I want to hear from you. Email me at podcast@usergems.com. 

And if you're looking for the ultimate revenue leader cheat sheets, sign up to receive them at usergems.com/podcast.