🚀 Breathe.



“I'm a firm believer that being a little bit irrational drives creativity in teams and also in using stories to drive productivity. I think that any leader needs to make room for their teams to be irrational, to take risks, and to not always make decisions based off of data."

In this episode

In episode #57, Kyle Lacy shares how to communicate ideas in an effective way and why he believes the best ideas come from irrationality. 

Kyle Lacy serves the marketing team at Lessonly as the Chief Marketing Officer. Prior to Lessonly, Kyle grew his leadership skills at ExactTarget, Salesforce, and OpenView. 

In this episode, Kyle discusses servant leadership and the difference between job growth and career growth. 

Kyle also shares how he encourages cross-collaboration with his team and why you should always be looking towards the future.

Tune in to hear all about Kyle’s leadership journey and the lessons learned along the way!

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Storytellings’ place in leadership


Irrationality drives creativity


Being a manager at 25


Stories about feelings


I serve my team


Bottom up ideas


Job growth vs. career growth


Lessonly’s skill matrix


25% for six months ahead


Parking lot ideas


The importance of meeting people



Aydin Mirzaee (Fellow.app)  00:00

 Kyle, welcome to the show. 

Kyle Lacy (Lessonly)  01:57

Hey, thanks for having me. 

Aydin Mirzaee (Fellow.app)  01:59

Yeah, this is gonna be super fun. For those that are just listening in and not watching. I felt very welcomed in the beginning of this conversation, because there’s literally like a picture of a superhero in the background there. I thought that you did that just because you’re on the Supermanagers podcast, but it turns out that you like superheroes.

Kyle Lacy (Lessonly)   02:19

I love superheroes. It’s great, it’s one of the illustrations from our CEO’s book and we have them in every conference room, at Lessonly.

Aydin Mirzaee (Fellow.app)  02:19

Yeah, that’s amazing. I like that. So because there’s a lot that we’re gonna dive into, you’ve obviously had an extensive leadership career yourself. You’ve been at Salesforce OpenView venture partners, and today, your cmo at lessonly. And before we dive in, I wanted to start by asking you who has been the most memorable manager that you’ve had in your career and why

Kyle Lacy (Lessonly)   02:51

Oh, man, probably the guy that I reported to at exact target Jeff Rohrs. I think that to be a good leader, you have to be a good storyteller in order for people to want to follow you and waterfall ideas. And Jeff Rohrs is one of the best storytellers that I know. He hired me at Exact Target. And he, he basically gave me He taught me the value of storytelling, as well as just giving somebody free rein to do what they want and be a very hands off leader. I think the best managers and the best leaders are very hands off with their teams. And as long as they’re hiring the right people, then giving their team the bandwidth to do something as important. 

Aydin Mirzaee (Fellow.app)  03:40

So that is super interesting. Tell me more about storytelling, because like, you know, for senior leadership in a company, I can, I can kind of see and imagine that and you know, this is the company’s vision, this is what we’re doing. How does that work for all levels of leadership, say like, your first line manager, like, what does that look like?

Kyle Lacy (Lessonly)   03:58

Well, I think that it’s just how do you communicate ideas and communicate it in a way that’s meaningful? So people agree with doing the idea, especially in marketing, right? Like that’s hands down, it’s very important that they agree with going along with it, and they believe in it. And the best leaders, the best managers that I’ve ever come across, can communicate effectively. And storytelling is just one of those ways to do that. Right? If you can, if you can tell a story appropriately. You’re going to be great at marketing, but you’re also going to be good at leading teams, because they’ll follow you and they’ll remember

Aydin Mirzaee (Fellow.app)  04:39

Yeah, so I guess it’s more about understanding the why. versus just like, hey, let’s just go do this.

Kyle Lacy (Lessonly)   04:45

Yeah, or just or just, you know, being a little bit. I’m a firm believer that being a little bit irrational, drives creativity in teams and in using stories to drive productivity. Using stories to drive messaging using stories to drive campaigns, can you know a little bit of irrationality is important for teams, especially for creativity? Sure.

Aydin Mirzaee (Fellow.app)  05:10

And you said irrationality, right? Oh, yeah. being irrational. Tell me about that. Like, that’s not typically a thing that that we normally hear, like, what does it mean to be irrational?

Kyle Lacy(Lessonly)   05:20

I’m gonna butcher the name of this book. But it’s basically, how do you, how do you make decisions on what to do while using data, but also being a little bit irrational. So a lot of the best ideas come from rationality so you know, there’s a direct mail piece that you think’s gonna work, because the data shows it’s gonna work and you did a focus group and all that. And then you come to find out that the actual rational idea that you didn’t test performed better, I think that any leader needs to make room for teams to be irrational and to take risks. And to not always make decisions based off of data. That’s kind of it’s from a book by Rory Sutherland. He wrote something like the lost genius of rationality. It’s like a TED talk that he gave about the psychology of irrationality. How to be less rational. He is president at Ogilvy, Rory Sutherland.

Aydin Mirzaee (Fellow.app)  06:19

Yeah, yeah, he did have a new book as well. I’m gonna Yeah, and I recently read it. And well, whenever it came out, I thought it was great. Yeah, we have to look that up and put that in the show notes, alchemy? Yes. Yeah. What an incredible book. So that’s really interesting. So storytelling, so you kick off your career. And this is one of the things that you notice in one of the managers that you like the most. And so now, when did you start leading a team yourself? Like, what were some of the mistakes that you made early on?

Kyle Lacy (Lessonly)   06:53

So it was at Exact Target, I was a year in I mean, this is outside of this is the professional setting, I had started an agency before exact target, we had employees. But this was right after I graduated college, it was just not like me, me as a 25 year old manager was not a good situation in general, but at an exact target. We built out a content marketing team in 2011. Yeah, 2011. And let’s see mistakes. Oh, man, I think I think the biggest mistake that I made early on was was placing too much of my self worth and ego into the role and not enough, and not having enough empathy for teams for the team, or the teammates, right is basically very much around what I thought was a great idea what I thought would catapult me into more leadership more responsibility, like I will, I was always asking for responsibility, because it fed the ego, it wasn’t necessarily that it was a good idea, at the time, and I and I’ve learned over the years is that in order to survive in a high growth, software environment, you need to be very aggressive. And if you don’t have the empathy side of managing teams, then you’re going to burn people out all the time, you’re not gonna be able to grow a team that can scale. So empathy is one thing that I failed miserably at, when I was a first time manager, I just didn’t have it. 

Aydin Mirzaee (Fellow.app)  08:25

I’d love to dive into an example of that. So for example, what’s the sort of thing that you know, the responsibility that you shouldn’t have taken on or just an example of what that might look like? So people have better pattern recognition to be able to see themselves? Sure.

Kyle Lacy (Lessonly)   08:41

So, half my time was spent speaking at conferences, and the other half was spent running this content marketing team. When I had the choice of what I would do, I usually pick the speaking engagements because it was more ego-friendly for me. So if I had a choice, a team off site, or you’re speaking at this email marketing summit, I would go speak to email marketing summon, the team would still function. That’s an example of putting myself over the team. And then there would be situations where somebody would be burnt out, or they were signaling that they were close to it, or, and I just didn’t, I didn’t understand how to see that. And I also didn’t care that much, which is not empathetic at all, which I have changed over the years. But those are some examples.

Aydin Mirzaee (Fellow.app)  09:33

Yeah. And so what are like what are some ways to watch out for, you know, people burning out I go back to the original thing that you said, as well, just like on the storytelling, because it sounded like when you first started You, You almost had like a, here are all the things that we need to do. And then just getting the team to operate and do those things and like can that lead to burnout or If they understand the why behind why they’re doing things, maybe that’s a different approach.

Kyle Lacy (Lessonly)   10:06

Yeah, yeah, say if you’re if they believe in what you’re doing, they’re gonna have, they’re gonna have more bandwidth, both mental as well as physical bandwidth just to get stuff done because they believe in it, I believe in the, the idea, you can never trust somebody’s ability to tell you, they’re going to burn out. So as a manager or a leader, you asking somebody, if they’re burning out, is not the best way to do it. What I’ve found over the years, and is that, and this goes to storytelling is that I will say that I’m close, or I will be very open, especially last year, 2020, just very open with the team saying I’m taking a half day because I need I need it, because I’m about to, you know, I’m about to burn out. And when you do that, that’s teams actually will be more open and honest with each other as well as their managers and as well as with you. Because you’re the one who started it. I think a lot of times managers give too much too much rope for people when they not like we’re assuming that everybody’s going to come to you and say I need to happen. And that’s not realistic at all. Because nobody, no, no individual contributor is going to go to you and say that, right? So telling stories about how I was feeling, how I was burning out how how my peers were feeling that I were talking to just helped. And it really set the stage for people to say, Hey, I’m also in that. I’m also feeling that way. And it just opened a dialog that wasn’t there before. So I don’t know if you can, I don’t know if there’s examples of like, Oh, hey, they’ve missed the deadline, or they look tired. Because I just don’t think that’s realistic.

Aydin Mirzaee (Fellow.app)  11:48

Yeah, no, that makes sense. I love just leading by example, and then doing things that seem okay. I mean, would you recommend to people that they almost even if they’re not on the verge of burnout to do things like that occasionally so that it does offer signaling?

Kyle Lacy (Lessonly)   12:05

Yes, absolutely. And it could be it doesn’t have to be just burnout. It could be anything, it could be like it could be I had a I had a rough conversation with my wife, my kids are being crazy, like being human goes a long way when it comes to empathy. and building a strong team is that look, it’s it’s I get the whole, you know, work life balance, maybe, but bringing, bringing your personal life to work and your mental, like mental health checks. And all that stuff is so important to building a team that can scale appropriately. It’s not just somebody who’s really good at a specific role, like search engine optimization, or ad campaigns or whatever,it’s that they can bring their whole self to work and do it in a way that’s meaningful. 

Aydin Mirzaee (Fellow.app)  12:48

It reminds me of something that you posted on LinkedIn recently, which is, I serve the marketing team at Lessonly. So tell us about what it means to serve the team versus how have the team serve you.

Kyle Lacy (Lessonly)   13:05

A lot of leaders have the team serve. So this came from a guy named Andrew Robinson AR three he was an engineering or product leader lesson way. And that’s how he would introduce himself, that at any function, he’s like, I served the product engineering team at Lessonly. And it was more just around servant leadership as you are there as a manager to support the people who work for you. They’re not there to support your rise, and getting promotions and stuff. I mean, that’s a very simplistic way to talk about servant leadership, there are plenty of amazing books to read on servant leadership. But for me, it’s, I exist. And I am here to make sure that the team that I am supporting succeeds at what they do. And that’s my job as a CMO. So when it comes to serving people, it’s what is what can I do to make sure that obstacles have been moved out of the way for the team to get done what they need to do and serve them in that way, not, Hey, can I just delegate stuff all the time and make sure that it’s done? Because the best ideas are coming from the bottom up, not top down. 

Aydin Mirzaee (Fellow.app)  14:16

So how does that relate then to goal setting and like where the direction for the team comes from? Especially when you say like the best ideas come from Bottoms up.

Kyle Lacy (Lessonly)   14:28

We have company objectives, you have team objectives that are set by management, but then the way that we do it at Lessonly, at least the marketing team, we have our revenue objectives. And then the teams are meant to come up with ideas to support those revenue objectives. So it’s really up to the individual contributors and the managers of each business unit to say this is what we think we need to do in order to hit these goals. It’s not us in an ivory tower, saying you need to do X, Y and Z. It’s a very community driven approach to it. But it’s more collaborative than anything else.

Aydin Mirzaee (Fellow.app)  15:05

Yeah. And that makes sense. And like, how do these cycles work? So for example, is that sort of on an annual cadence? I’m just trying to get a, you know, you’re you mentioned, you’re about like 250 or so employees there right now. So at that kind of scale, what does the planning look like?

Kyle Lacy (Lessonly)   15:22

You’ve got annual company objectives that are set at the beginning of the year. And we do that usually over December because we’re February fiscal, sorry, Your starts in February. And then each team lead, each executive member comes up with their team, quarterly objectives that align to the company objectives, and then individual contributors have their personal objectives that align up all the way up to the top of the company objectives. So it’s not quite as intense as like Salesforce is B to mom, which I highly recommend anyone check out because it’s brilliant, how they set that up internally. But it is it is a bottom and it kind of meets in the middle, like the personal objectives of each individual, the company objectives, and then the team objectives in the middle kind of support everyone. 

Aydin Mirzaee (Fellow.app)  16:11

Cool, that makes a lot of sense. So, we’ve talked about now like the goal setting, serving the team, one of the other things that you also talk about is, you know, the difference between job growth and career growth. One of the things that you say is you’ve really got to care about your team’s career growth, what is the difference between job and career in that case,

Kyle Lacy (Lessonly)   16:35

I think I think it’s very much dependent on the job that you’re in, and the career that you’re in and venture backed software, you like companies are created and die within two to five to 10 years, like there isn’t a this is my parents, I worked with somebody for 55 years in some manufacturing plant, right, you’re gonna have 10 jobs by the time you retire, or you just keep working, right? So for me with my team, it’s very much supporting a career because the job and lessonly is finite, right? It will, they will work, Leslie will succeed or fail, and then they’ll go on to the next role. And for me, I’ve talked to way too many people that put their head down and do not create a community or a network that don’t talk to people outside of their companies. And when the job ends, they don’t have a career to back it up. They pick their head up, and they’re like, oh, where do I go now. But if you work on building a community around a career, so like, if you want to be an account executive, Leslie, you should also be talking to a bunch of account executives and account and sales managers, at other software companies, because just in case, it doesn’t work out a lesson, Lee, you have the opportunity to go to these other places, because you built relationships there. I don’t think a lot of people I know don’t think that way. Like it is, it does not come naturally that you would go talk to other companies. So that’s what I mean is that you, you want to succeed at your job, we hired you for a role to do and we want you to hit those metrics and those KPIs. But the reality is that your career might not necessarily be to let you know, your next job might not be here. So you need to think very proactively about that. And then I help if I have people, if we have other companies trying to poach my teammates, I’ll talk them through the deals their offers, and I’ll give them a straight up answer on whether I think it’s a good career move or not. And we’ve had people leave Lastly, at least the marketing team because the deal was great, and it was a good opportunity for them.

Aydin Mirzaee (Fellow.app)  18:45

Yeah, that’s a very, like good kind of, like long term approach to take there. And certainly not very typical, like you said, Are you then also doing things like, you know, career check ins with people’s, for example, like in your one on ones? Or? Or how do you schedule? Like, how do you make sure that while they are at lesson lead, they are also able to get to their career objectives even at the company. 

Kyle Lacy (Lessonly)   19:13

There are a couple things that we are implementing, it’s not perfect, but  we have a product called Skills, where we are building a skills matrix for each individual on the team to develop skills towards their career. And then I meet with every individual quarterly for 30 minutes. So at the first two weeks of every quarter, I basically have 45, 30 minute meetings, basically and we are talking about their career in those meetings. And I’m asking them, like, Who did you meet last quarter? How are you? How do you feel about this field of marketing or compare this account executive role? That’s kind of how we approach it. We’ve had we’ve played around with objectives related to career but it’s really around enabling somebody in the role that they want. So if an SDR on the marketing team wants to become an account executive, if they hit certain goals, they get to go into account executive enablement. So there’s a lot of different things that we do. But for me personally, I’m spending at least 30 minutes every three months with each team member talking about it.

Aydin Mirzaee (Fellow.app)  20:16

Yeah. And so this is across the organization, obviously, like you don’t have 45 people directly reporting to you. But you’re actually meeting with everybody, then.

Kyle Lacy (Lessonly)   20:24

Yeah, all 45 people on the marketing team, Yeah, at least once a quarter. 

Aydin Mirzaee (Fellow.app)  20:28

And so how does it work? In terms of like, the, I’m just thinking of the agenda for this meeting? Is it that they come to you and say, like, here’s what we think our goals are, or, like, what happens in those 30 minutes?

Kyle Lacy (Lessonly)   20:41

We definitely follow the start, stop, and continue. Like, what, what? And they bring that agenda? And then I will bring up more career conversations. So the first 15 minutes, we’ll be talking about the past quarter, like or how do they feel? What should we start? What should we stop? What should we continue as a team as well as me as a leader? And then the last 15 minutes is, and this is not a perfect science, but the last 15 minutes, we usually talk about how you were thinking about your career last quarter, you said you want to become a county executive, but I’ve seen you meeting with the field marketing team? Like how do you feel about that? Like, how many people did you meet outside in the community? You know, how many peers did you meet? So it’s more? It’s not necessarily career development as much as it is network development, community development for the most part.

Aydin Mirzaee (Fellow.app)  21:30

Yeah, that makes sense. And so you’re then spending a lot of time talking about all the meetings you’re having, but you’re probably ending up doing prep work for all these things as well. So this is like a significant effort.

Kyle Lacy (Lessonly)   21:42

Yes. Yeah. And Well, look, I mean, we bought we, you and I both have been in situations where, you know, especially in a town like Indianapolis, where Lessonly is one of the largest software companies right now outside of Salesforce, which has a huge office here. You’re going to be working with these people again, at some point, right, that’s just reality. You know, we hire the best and we want them to be the best. And I don’t, you cannot be the best at what you do without thinking about community development and networking and meeting people outside of your office. I mean, it’s just, it’s something that I have taught my dad very early on. And it’s been a huge part of my success over the past 10 years.

Aydin Mirzaee (Fellow.app)  22:26

Yeah, I think I think that makes a lot of sense. And, you know, I mean, there’s no way I mean, it’s such a great way to show people that you really, really care. And I think that that comes across and I love this just the idea of playing the long game, because you’re right, like careers are winding and you come across a lot of people.

Kyle Lacy (Lessonly)   22:43

Yeah. Look, I met a gentleman named Scott Dorsey who was the CEO of Exact Target when I was 25. But I was running an agency, it was a mess. I had no idea what to do. I had met him for like, five minutes at a net-added event. And I randomly emailed him out of the blue and said, Hey, would you take some time to talk to me about a problem I’m having in my business? Keep in mind, he at the time, exact target, over 100 million in ARR. Like they are just killing it. And he talked to me for 45 minutes driving home one night about how he didn’t even know me. They had no idea who I was. And he has been an integral part of my entire career. Like I joined the exact target. Because of that, I went to open view, because Open View is an investor at Exact Target and Scott’s on the board at Lessonly. Open View is an investor in Lessonly. And every time I have a major inflection in my career, I will call Scott and talk to him about it. And if I can do that, for just a handful of people, like that’s what I want. I think that’s true. I think that is true servant leadership, if you can do that, and you are, you’re selfless with your time with the people that are reporting to you. I mean, it just makes so much sense that that’s what a leader should be and do.

Aydin Mirzaee (Fellow.app)  24:12

Yeah, no, I love that story. That’s so incredible. And yeah, and I love it. I love it all. It’s basically like really showing servant leadership. So one of the things that we kind of also talked about in this conversation, which is not trying to do it all yourself. And so like you said, a lot of the ideas come from others and, and I feel like this is a thing that a lot of new managers have an issue with, right you just get promoted to the role and you go from like, maker to manager and, and then you want to feel productive. So you want to, you know, be doing more things and walk us through that. Like how do you, how do you make sure that you’re not trying to do it at all?

Kyle Lacy (Lessonly)   25:03

Oh, well, I think it’s how you manage time, number one. And it really depends on what level you are. And I think it’s more about forward-looking type projects. And it is getting tactical and granular like getting in the marketing automation software, looking at the analytics, like you, you have a teammate that should probably be doing that for you. But for first-time managers, I encourage them to set at least 20% to 25% of your week should be spent looking six months in advance, like, what are you going to be doing? What is your team going to be doing six months from now? And then as you move up to director level, senior director, VP, executive, that timeframe just gets larger. And so for me, most of my time is spent thinking about next year, and how I can support the team. I’m not doing very many tactical things. Because as the company grows, you’ve got you it’s your responsibility, like we talked about before, to remove obstacles, but I think it’s how you structure your week, like if you haven’t spent time, I mean, deep works a great book by Cal Newport, right? When it just has to do with just productivity and time management. If you haven’t structured your week appropriately, and you don’t have work blocks and you understand what you’re going to be doing, you’re going to flow back into the tactical, because it’s gonna give you a dopamine hit when you set up an email to send. And that’s and that’s the reality, right is that we, we want to end the day feeling like we did something and the way you do that from a strategic person, you know, when you’re thinking about strategy is that you have work blocks that, hey, I’m going to spend 60 minutes tomorrow, thinking about q4 and how we do x. And once that 60 minutes is up, and I have a bunch of ideas, great, I accomplished something. So I think it’s, I think too many times managers don’t structure their time appropriately. And then they always just flow back to what they were doing beforehand.

Aydin Mirzaee (Fellow.app)  25:34

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Kyle Lacy (Lessonly)   28:15

Yeah, so my time blocks are usually between four and 6 am. 

Aydin Mirzaee (Fellow.app)  28:23

Wow, that’s early.

Kyle Lacy (Lessonly)   28:23

Because the reality is, yeah, well, I’m an early riser. But the reality is, I don’t have because of removing obstacles, firefighting, sitting in exact meetings, like having calls with team members, I have five for direct reports. I don’t have the luxury of having 60 minutes in the day to do that. But I don’t because I want my team to be able to do that. Right? Like I don’t want to, I don’t want my managers to be so busy that they can’t think, like we just we’re dealing with this right now, like a lot of my direct reports are in meetings all day. And we’ve had discussions as a management team saying, this is not this, this cannot be the way we do this. Because you’re not thinking strategically you’re thinking about how do I accomplish 10 zoom calls in you know, from nine to five. So as an executive, I think it’s your job to remove those obstacles. So your direct reports and the reports under them have the opportunity to have a deep work every day. And so for me, if I’m thinking about next year, I’ll set aside 90 minutes but it but it’s not every week I’ll do it once every other week or once a month where I’m just alone, and I don’t have the phone on or anything so I can think but outside of that it’s pretty much meeting to me.

Aydin Mirzaee (Fellow.app)  29:50

I think that’s super helpful for people to kind of get a sense of what it looks like. You know, at your level and at that kind of company size. I assume you must also have systems though, because I find that like, Can it be difficult to say, okay, go 90 minutes, all ideas must come now versus like, I guess you’re probably also jotting things down but like leaving time to think about them deeply during those periods.

Kyle Lacy (Lessonly)   30:18

So I like the parking lot, I  recommend a Remarkable tablet. I don’t know if you’ve used it, but it’s basically a note-taking tablet. And I have a notebook in there that’s just parking lot ideas where I’ll randomly jot down stuff. So it will either be time spent thinking about some of the ideas that are there or it will be a chat, as an opportunity for improvement or a challenge, right? Like, hey, and the team isn’t performing well, our pipe gen is low, or we’ve got a huge product launch that’s happening, that we think is going to happen 12 months from now. And then so that the system’s around that I’m not very systematic, to begin with, it’s more just me laying out what the challenge is, and then trying to come up with as many ideas as possible for my team to bet. Because it’s really, they are going to be the ones that are going to say, hey, love those ideas, but they’re not realistic, or they’re gonna say, hey, that one idea that you came up with out of the five makes sense.

Aydin Mirzaee (Fellow.app)  31:17

I think that makes a lot of sense. So the other thing about marketing in particular, is that I mean, all departments, but you know, marketing definitely has a lot of cross-functional collaboration that happens, right? You’re, and it sounds like in your team, you have some salespeople, as well as sales-type functions. But certainly, marketing works with everybody in the company. And so one of the things that I’m curious about is, you know, how you encourage collaboration, you know, amongst teams, like teams that are in your company, like it basically under your organization, like how do you make sure that collaboration is happening with the other teams, and they really understand each other and build empathy?

Kyle Lacy (Lessonly)   32:02

Yeah, so we actually have pretty strong systems in place for alignment. It’s kind of specified to describe this, it’s very tactical, but we have a revenue effectiveness team and a revenue operations team that kind of lives in the center of our revenue teams. So cx sales, support, or services and marketing. And they are responsible for alignment. And so what we have is my managers meeting with their peers, at least bi-weekly, we have a weekly funnel and pipeline meeting with all revenue leaders, where we’re talking about what happened last week, what does the quarter look like? How’s the forecast looking? How is pipe chat and all that stuff? quarterly, we have a revenue and experience summit, where it’s basically a core QPR, but each manager, each business unit leader is responsible for talking to each other on setting up objectives for the quarter. And then it’s and then it’s making sure that when I’m meeting one on one with my managers, weekly, we’re talking about, Hey, who did you meet with last week? Is there any, you know, let’s start to stop, continue, we use all the time. And that’s kind of how we align and it’s weekly. And that’s so that but the revenue ops team is the one that runs all this stuff. And because they are the data, and then the revenue effectiveness side is the training and enablement of like, what do we need to do in terms of just deal support or demo support or onboarding all this stuff? And so it’s kind of their hub to split the revenue spokes, which is terrible visualization, us talking about storytelling, I can’t tell. Can’t tell a very creative story there. But that’s kind of how we do it from the linemen perspective.

Aydin Mirzaee (Fellow.app)  33:48

Yeah. So I think what’s interesting about that is like, I’m curious to know, when, for example, you created some of those meetings or regular cadences. I assume that like you, was it you just came in? And you said, Well, these are the things that need to happen. So let’s put these things in place, or was it hey, we have this problem. And so this needs to be looked at, say on a certain cadence?

Kyle Lacy (Lessonly)   34:14

Well, I think that the funnel and pipeline meeting I helped implement the first year I was at lustily 2017. And that’s because we weren’t anybody was looking at anything. Now, this was, this was pre 5 million in ARR. So it’s kind of there wasn’t anything in place to go to, to check where we were at. Right. So I would say that that was probably the challenge is that there wasn’t any there wasn’t. There wasn’t any meeting where everybody that owns revenue is in the room. The revenue experienced in summer we’ve only done it once. It’s fairly new. And I think it just, it was mostly just around. There wasn’t a lot of communication between mean frontline managers and then directors and VPS with each other, and everybody’s kind of setting objectives separately. And, and, you know, that’s okay with 100 people, that’s okay when everybody’s an IC. But when you’re hiring 50, Indianapolis where we’re headquartered, I guess we should probably say that when you’re hiring 50 to 80 people a quarter, and most of them are remote, you have to have some type of vehicle to make sure that objectives are aligned, because individual contributors or even frontline managers, it’s going to get just too chaotic, because there’s just so many people that you, you know, your onboarding or that have been here, but they have objectives that they need to hit.

Aydin Mirzaee (Fellow.app)  35:44

Yeah, no, I think that that’s super helpful and gives everyone a sense of the systems that need to be put in place and, you know, various growth stages. Speaking of growth stages, you spent some time at Open View, which is a venture capital firm. What lessons Do you think that it helps you learn from going from like, you know, an operating company, it sounds like you’re a part of the exact target when it was acquired by Salesforce. So you’ve certainly been through hyper-growth at different companies, a large company, going to open view and now you know, a scale-up so curious what lessons you learned, during your Open View time?

Kyle Lacy (Lessonly)   36:27

Personally, I learned how I learned alignment, because, at a venture capital firm, you have basically the partners who are your boss, right? So you have like seven bosses, or eight, depending on how big the firm is. So making sure that everybody was heard, and everybody was aligned was very important. I learned that firsthand, at OpenView. The other The most important thing that I applied to Leslie was, what different stages of growth looked like, like what team structures looked like at a series, a sub 50 employees, what does the team structure look like? If you had just raised $100 million, and you’ve got to hire 100 people, that was probably the most valuable thing, and just talking to peers, like I being part of a venture capital firm that has an operating team, you’re looking at 20 different portfolio companies and how those leaders, you know, are scaling, and some of them are doing well, and some of them aren’t. And so you get to see all of those different examples. That was probably the most important thing that I like to say, Exact Target was, I mean, I, the year I joined, we hired 500 people, I’m pretty sure. So it wasn’t like it didn’t matter. Like we could have gotten there and just failed completely the whole time. An Exact Target would have still IPO, they still would have bought two companies, and they would have been bought by Salesforce. So when I got to open view I basically got a master’s degree in software and hydro SAS. And that’s in the best two years that I’ve spent, it really set me up for success here. Because I got to see it firsthand.

Aydin Mirzaee (Fellow.app)  38:01

Yeah, no, that’s amazing. Like just that kind of pattern recognition. And I guess for people who maybe can’t work at venture firms. I mean, your community approach and meeting people at other companies is, I mean, you have to do it.

Kyle Lacy (Lessonly)   38:15

Go meet with people at a venture capital firm. Like I got, there’s, it’s not like they’re in an ivory tower. You know, they’re trying to build a network just like you are. Right. So, you know, I just think that the more people that you meet, as long as you’re being productive with your time like you shouldn’t have 10 zoom calls a day, right? Just meeting people, like you have a job, make sure you do your job. But it’s so important to meet people because you will be a better employee, and you’ll be a better person because you’re just learning more. Like I spend a lot of time with peers with other CMOS at all different stages of growth, because you’ll walk away from the conversation learning something, and that’s so important. Yeah,

Aydin Mirzaee (Fellow.app)  38:59

I think that is amazing. And so, you know, it sounds like you meet with a lot of people do you also have I think like the founder of Exact Target was one of those kinds of like mentor folks for you. Do you have other people in your circle that also serve kind of like a mentorship role?

Kyle Lacy (Lessonly)   39:18

I do have a, I don’t want to say a career coach because he’d probably make fun of me for saying that but Gonzo who led marketing for Ot Zero, who’s now at a more of like a growth stage company. I meet with him bi-weekly to talk about marketing. And then you know, a lot of us are involved in the revenue collective, which is a community of high growth, exacts. And if I have a question or I have a problem, I’m usually going to revenue collection and talking to four or five CMOS that might have dealt with something in the past and I’m dealing with today. So for me, it’s I have my chosen few people that I’ve worked with for over on time and that I definitely have a career coach when it comes to well, don’t tell him I said he’s a career coach, but he’s, he’s been coaching me over the past month. Maybe a growth coach. That’s better that’s a better way to put it.

Aydin Mirzaee (Fellow.app)  40:15

 Yeah. No, that’s, that’s awesome. You know, Kyle, this has been super valuable, so many different insights. And like, certainly from like different stages of companies. And like we’ve kind of started from, you know, when you first started leading teams to all the way now leading, being CMO at Lessonly. One of the questions that we ask all of the guests on this show is for all that managers and leaders looking to uplevel and get better at their craft of managing and leading teams, are there any, you know, books or resources or tips or tricks or just parting words of wisdom that you would leave them with?

Kyle Lacy (Lessonly)   40:51

This is gonna sound self-serving, but I’m gonna say it anyway, Do Better Work. But it’s a book by Max Yoder, as our CEO, it is one of the best books on leadership I’ve ever read has nothing to do with lessons. It has everything to do with our values as a company and how he built the value of the foundation. And it’s all its chock full of great stories on servant leadership, nonviolent communication, doing your best work, you know, sharing before ready all the values that we talked about a lesson late. It is it’s, it’s an hour and a half-read. It’s on Amazon do better work. It’s it is amazing. It’s an amazing book, highly recommend that I brought up four times.

Aydin Mirzaee (Fellow.app)  41:36

Wow, four times. That’s pretty good. That’s amazing advice. And we’ll link to that in the show notes. Kyle, thanks so much for doing this. 

Kyle Lacy (Lessonly)   41:44

Thank you. It was a pleasure.

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