The First 100 Days of an Accidental Marketer with Kevin Marasco

Kevin Marasco, the CMO at Zenefits, joins us to discuss what to consider when evaluating your next career move. Kevin’s philosophies led him to a variety of positions, which eventually led him to marketing. Taking the next step as an entrepreneur or employee is challenging, so tune in to learn how to position yourself for a successful transition.

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The hosts:
Trinity Nguyen
Christian Kletzl

In this episode, you’ll learn:

  • How to evaluate your next career move
  • How to handle career challenges
  • How to evaluate the benefits of starting your own category or outperforming others in an existing category as a start-up
  • How to add value during the first 100 days

What to listen for:

  • [02:49] How to evaluate whether a role or company is the right fit
  • [08:00] Understanding failure
  • [10:34] Staying calm through challenges
  • [12:16] Creating your own business category or outperforming others in existing categories as a start-up
  • [16:19] How to add value during the first 100 days as a marketer

You can also check out his blog post here: "Embrace the Learnings with Kevin Marasco"

Reference Links:
Guest headshot

Kevin's passion for learning is embodied in his unconventional path to CMO. For the past 20 years, his focus has been sales and marketing, specifically the go-to-market side, in leadership roles at various high-growth public and private B2B SaaS firms. With 10 capital raises, an S1 process, and 12 M&A deals behind him, you might say he’s done it all.

Read Transcript

Kevin: It could be a bad day. It could be a failed marketing campaign. It could be a bad day of leads, but Hey, look at why did that happen? And how can we learn from that and build from that and then share those learnings with the team. I think that's the important thing, is to embrace the learnings.

Trinity: Welcome to the First 100 Days, a show for revenue practitioners by revenue practitioners, giving you unscripted access and exclusive resources to help you navigate any new transition or initiative. I'm your host Trinity Nguyen, from UserGems. Kevin Marasco is the Chief Marketing Officer at Zenefits, a disruptive software company, powering small businesses to shift from HR to people operations.

Kevin embraces changes with ease throughout his career with a "Why not?" Mentality, which accidentally landed him in his current field of marketing. To kick off our conversation, Kevin reflects on pivotal moments that unknowingly accelerated him forward 

Kevin: Career, it is a journey really, in an accumulation of experiences and learnings.

And so to me, I try to just like really embrace that, that journey, and feel fortunate to have just worked with some really amazing people and learned a lot of really neat things from them and from the experiences, you know, as well. And so I guess if I look back some of the milestones, the pivotal moments, if you will, were big decisions, and usually it's like a decision to join a company.

As I look back, like every job I've had, I actually started with no, Hey, I'm doing this other thing. After I had a conversation and then reconsidered and like, Hey, maybe I need to do this. This is a big decision, a big move. Similar milestones exist within a company, like a decision to launch a new product.

Change your strategy. Change the go to market motion. Signing a big new customer. Launching a big event, a big campaign. It's those big and kind of those big events that I think back, are those pivotal moments and whether it was a success or failure, it was a big event and you learn something from it. It might've been good in many cases. In my case, there were bad outcomes, but it was the actual experience and what you learned and then how you can then parlay that to your next experience and what you do next. I think it's interesting, as you look back, you pick these milestones, and sometimes you didn't know it was a milestone at the time that you'd look back on, but those were a lot of the events. I just kind of try to think about it as, like, an accumulation of experiences and learnings.

For those 

Trinity: who are looking to join a company, it could be startup or larger organization, what would you advise them? What were the things that you looked at and now that you know better, like, what were the things you wished you had looked at to evaluate whether a company is a right fit? 

Kevin: That's a great question.

Early in my career, I had a really myopic view. Who's working there? What's the company's brand? How fast are they growing? Type of thing. I think as I've matured, I like to think I've stepped back. Now I look at life's too short. You want to make good decisions about the decisions you make, especially when you're committing a big bucket of time and energy and calories to something. So, I want to look at the market. I tend to try to really paint a market, whole market view. What's the category? What's the potential of a category? Not just necessarily what it is today – more importantly, what could it be?

Yes, size is part of that, but that's really only part of it. And you're going to have an opportunity to create that, right. So you want to look at it really from that lens, the potential of the category you want to look at. The company itself, like the DNA and characteristics, everything from the culture, the team, the leadership team, who are you going to be working with, and then all the forensics, the investors, who are the investors, what stage are they at? What does success look like for them and what's their timeline? What's their track record and history? Really kind of understanding, having a good 360-degree view, because all those things can have a big impact on the path of the company.

And sometimes it can be things – and I've learned this the hard way – beyond your control and sometimes beyond even the company's control. So, really trying to get a feel for some of those constituents. At the end of the day, I'm looking for what could be a big opportunity, a company that's well-positioned to take advantage of that opportunity, and then my ability to move the needle and make an impact. I like to build and create things. So can I come in and help move this along in a positive way? This is going to be a fun and enjoyable experience for 

Trinity: everybody. From what you said, basically assessing the company, the competitive landscape, the potential of the category, but you mentioned that you also assess what kind of impact you can bring to the company. So, what do you recommend people to do, some kind of introspective exercise or StrengthsFinder, et cetera, to kind of see what – it's like a Venn diagram where the two overlap? 

Kevin: Absolutely. Let me first, let me break it down, too. What I tend to do is I tend to do due diligence on an opportunity, like I would any type of deal. I want to talk to customers. I want to talk to competitors. I want to talk to the board, the management team, et cetera. It's a serious investment that you're making, right? So you want to do that type of due diligence cause you're voting with your career. So you want to do a good bit of due diligence and understand that, number one, to decide if you want to join, but also to start to map out what a strategy would be and what your ability to make an impact would be. So I think first you want to start with good self-awareness where you can come in and add value – what your strengths are and what your strengths could be. And then map that to what the needs are of the company and how that aligns to what you think the trajectory of the opportunity will be.

It's easy to get caught up in just making a decision to, Hey, I can go and make an extra X dollars here or get this bigger title here. That's short-term thinking. But before you just jump to that decision, step back and try to think about it holistically. What am I trying to do? Am I trying to build career equity?

What does success look like for me? What does that path look like? And then how well does this opportunity fit into that vision I have for my own career. I will say one of the learnings I've had, I mentioned that a lot of times I wasn't planning to take an opportunity. So in one case, I started a start up.

We built it from zero to 500 people and then a public company bought us and we were competitors. And my initial reaction was, there's no way I'd work for this company. As I met the team, I had to tell myself, Hey, don't jump to a conclusion. You can't do that as a marketer, right? You have to always understand your buyer, who your customer is.

And if you just jump to judgment, you're not doing yourself a service. You have to do the same thing with your own career. As I assess the situation, I said, Hey, here would be an opportunity. In this case, I was actually taking a smaller span of control. I had owned all of marketing, sales support, inside sales, and now I'm just going to have a part of marketing, but as for a publicly-traded company where I can get some public company experience and work with some different folks who are doing different things at a different stage.

I said this would be a great learning opportunity for me. So don't worry about the title. Don't worry about, you know, how big your team is or what your paycheck is. Here's an opportunity to learn something new and exciting. I decided to go for it. So, if 

Trinity: someone's listening to this, they might say, well, maybe Kevin you've been so lucky and things have been kind of smooth sailing for you.

I'm going to drill into the word failure that you mentioned earlier. So last year you mentioned that one of your favorite books was Obstacle Is the Way by Ryan Holiday, where he talks about turning adversities into strengths. So what would you say was the greatest obstacle that you faced probably in your career, and any kind of transition, maybe through an M&A, or launching a new go to market motion, et cetera, what did you learn from it? And, if it was a failure, what did you love? What would you do differently this time? 

Kevin: As I look back on my career, I think I've had more failures than successes. But I also think that's okay because I think I consider the failure, learning. I'd say failure, at whatever level, early on, we were taking a company public and we went all the way down to selecting our bankers, develop the S1, and you know, you have hundreds of employees excited about going public and ringing the bell and all that thing. We had a last minute issue happen and lost the market window, and so we didn't go public. So I would say, Hey, that's a failure. Like we didn't do what we planned to do, but a different opportunity came.

We learned a bunch of things and we ended up going in a different direction. In every company I've been at there's like 20 of those stories. Like we had a failed product launch. We went to market the wrong way. We were enterprise and we tried to do self-service, swipe your credit card, for an emerging category and it failed miserably. Almost ran out of money multiple times.

There's all these stories behind the scenes of companies. It's easy to see the headlines of the huge successes, but often what's missing is the failures. You kind of need to embrace it. You're going to have challenges and you have to look up these hills and it's how you deal with that and manage the situations.

Just kind of embrace it. Hey, there's going to be adversity. There's going to be challenges. It's how we embrace and learn from those. Perhaps just me, you know, being a runner and it's kind of like, you almost embrace a little bit of pain, right? It's like, well, look, anyone can do it. You just start. It's one mile at a time, one step at a time. You just put one foot in front of the next. It could be a bad day.

It could be a failed marketing campaign. It could be a bad day of leads, but Hey, look at why did that happen? And how can we learn from that and build from that? Then share those learnings with the team. I think that's the important thing, is to embrace the 

Trinity: learnings. You mentioned the running. So in running, you can at least measure it.

Like just take one more step and then one more step. So there's a thing, like if you improve just 1% every day, then by the end of the year, you're like, I think 37% better than where you started, but in work life, sometimes it's a little bit harder to measure that precisely like running. So do you have any kind of personal tips on how to keep yourself basically stoic and calm and just be patient.

Kevin: I think having some level of balance in Zen and in your life can help. So for me, like my way to do that is running, meditation, trying to eat fairly healthy, right? That kind of keeps you like balanced and keeps your head level to where you can deal with adversity, with continuous change, and you're able to kind of keep a level head and make smart decisions and kind of evaluate your progress.

I think starting that and trying to create a culture of that, where, look, we live in a world of chaos. Right. And it's all about keeping a level head and taking in data and insights and be like, okay, Hey, what do we need to do next? And sometimes that's one day at a time and same in business. So it's, you do need to find a way to measure though, right?

That's like, different for every company at every stage, but you need to be looking across how are we doing with customers. Like, what's our NPS, our response times, our net and gross retention. So you have to pick those measures and continue to look at those and track them daily, weekly, monthly, and annually.

Trinity: So just switch gear a little bit on the, to like the business questions. So you turned to newcomer companies like RecruitMax, Vurv Technologies, and then hired you from being a newcomer into a category leaders. What would you advise the startups now? Whether they should create their own category or join existing category and outperform the competition?


Kevin: any doctor or lawyer would say, it depends. It really. First of all, I love category creation. It's one of my favorite things in marketing. I find it fascinating and I love it. It's one of my favorite things to do. So I tend to lean in that direction personally, but checking that bias aside, it is a situational. It's definitely, I would say any company should consider it and step back and take a look, does this make sense? What's the current category? What's the perception of that? What does the competitive dynamic look like? Where are we at in our stage of growth and where are we going? What do we think that path looks like? Could we be better off basically breaking off a piece of the category to create a new category completely?

You know, is it a paradigm shift? Is this creating something entirely new in white space alone?  Understanding and making a decision on that. It does take a commitment. It does take time. It takes resources to do it. So if you're, you know, super early startup with two people, It could make sense, but just know what you're getting into and what it will require to be successful.

If you're a little further along and have the resources and the time to put behind it, you just need to think about that. But it's absolutely something that I think everyone should at least consider and take a position on. Know where they are. It might be a thing where you say, Hey, yeah, we're going to do this, but it needs to be 24 months out because we need to get initial traction with product market fit.

Then we can really parlay more investment into that because it does take both a time and capital commitment and you want to be able to do it right. 

Trinity: And unless someone else joins that category, you yourself cannot be the category alone, right? So, it's not only just like building out your ARR and doing the promotion for your category, but someone else has to agree with the category and join and say that they are part of this category.

So at least two companies in one category to be considered as a 

Kevin: category, right. That's right. And it's really interesting because there's areas where – you know, rising tide lifts all boats, right? So you could be an instigator to a category creation. You might be early stage, but you say, Hey, if we create a new category or reposition this category, this way, it would benefit all these players.

And maybe it breaks the market in half, but you would benefit from the market breaking in half and a rising tide lifting. In one of my early companies, we did exactly that. It was, there were all these different terms for hiring software, right? Applicant tracking, you recruiting, all these things. We started a few basically and said, Hey, we're going to call it talent management.

We started working with the gardeners and foresters and, you know, advocating, and finally the newer players aligned on talent management. And, at least, back behind legacy providers and that actually benefited the category and everyone in the new category. Then there's other cases where you have to create an entire category just for yourself, where you can only, you do that.

So that's where you kind of got to think about a strategy that can depend on where you are. Sometimes you can pull resources, other times you want to just go it alone and just own the category. Then there's also the case where it's not necessarily the first that owns it. Someone might start it and spark it, but then someone with more resources comes along and kind of steals your position.

So you just want to be mindful of those things and think about your timing. There's not like a one size fits all playbook for it, but again, I think it's something that everyone should think about and consider. 

Trinity: So to get back to our main theme of the first 100 days, what's your advice for those going through a new transition right now, maybe a new job or a company pivoting?

Kevin: The first 100 days going into any big change, a new job, a pivot of a company or anything like that – in today's world a hundred days, like, that's a lot of time. Facebook was built in two weeks. You need to come in and add value in that first 100 days. So really, I think the 100 day starts before. You should be doing all your homework to understand some of the dynamics around the category, understand who the competitors are.

Customers think their perception of value in the category, and start to formulate some hypothesis. You don't want to jump to a decision or specific direction, but at least get some ideas on the board to be thinking about, Hey, thoughts on the category. Thoughts on the go-to-market motion, thoughts on our ideal customer profile, thoughts on marketing channels and strategies, thoughts on data and metrics, right?

Then you've kind of done good homework and groundwork. So when you're coming in, like the first hundred days, you can immediately add more value in every conversation you have. You're talking to your team, you're talking to your peers, you're talking to customers. You're like, okay, you have more context and you can go deeper and start to really listen and understand and start to build out.

Yeah, I'm trying to do two things. I'm trying to build out hypothesis of ideas we want to test, but then second, add short-term, almost near immediate value on little things where you're not coming in with a specific opinion or playbook, anything like that, because that can backfire, but at least, Hey, we're trying to move this well, Hey, can we do this, that might move it along a little faster? A lot of times it's just listening and understanding like, Hey, how is marketing, helping? What are some of the challenges with marketing, sales, or whatever the situation is? I think just kind of twofold, like trying to add value, but also listening and then you can accelerate that time to value if you will, by combining some of the pre-work with then quickly getting like this 360-degree view of the situation and opportunity.

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According to reviews and G2 Crowd, and I quote, "User Gems is a prospecting miracle. If you're in a revenue role, check out"

What do you think, Christian? 

Christian: What stuck out to me, because we're currently hiring, is the way he's making the decision in a sense from the other side. I found it so interesting that he went into this direction. Just how big of a decision it is for you.  I think that's what I always highlight to the candidates because when I talked to VC and they're spending other people's money, they're still making these men, like they ask for so much data, they evaluate every aspect of the company. It should be the same for a person making a career decision because ultimately you're investing the most valuable resource, which is your time. Therefore you should ask for the same amount of information pretty much. If there is an investor that asked for the investor deck, because ultimately you only have one shot for the next one, two, three, four years, and you want to make sure that it's the best shot. As he mentioned, it's a combination of two elements. It's how well is the company doing in their category? How much are they growing? How excited am I about the company? And then the second part is this, is my skillset a good fit to drive this forward?

As you mentioned, this Venn diagram of is there an overlap between my skillset and the skills that the company needs? 

Trinity: I think that the phrase he used and I really liked is you're voting with your career when you're evaluating a new job opportunity. I think is so true. And I like the fact that at User Jams, when we extend an offer and the candidate is interested, we usually, actually, we proactively suggest to the candidate take a look at the investor deck because if someone else wants to put money into this company and you're basically putting your money, time, resources, emotional investment into this, you should have the same amount of information as well. So I love that. And the Venn diagram is great.

I feel like a lot of time, maybe I'm biased, but based on what I've seen so far is people tend to – like the Venn diagram – one is understanding yourself, and the other one is understanding the space, which is the, how the company is doing the competitors, the trajectory of the space. A lot of time, people, kind of, they only do one or the other. I've never seen anyone actually thinking about both. Either they, kind of, like my background is, say, content marketer, or my background is sales for software. Therefore I'm going to find a job that has a title that matches that because that's an easy search. But they don't really look at it the other way around – which space is it at, how they're doing in terms of the competitive landscape, et cetera. Or sometimes the other way around, kind of, like, you see some shiny brands and you see when you drive down the 101 and you see a billboard.

Like, that sounds great. They doing great in that space, the space is growing. So you love that space, but then you forgot that, wait, am I really a right fit? Can I bring anything to this? Or is it I'm just trying to hop into the rocketship and hopefully it will take me there. 

Christian: But sometimes it's also hard, like the way he described it.

I want to talk to customers, talk to investors. You can do this if you apply for the C-suite, but this ask is much harder if you're an individual contributor, for example. 

Trinity: Agree, but there are also a lot of third-party review sites. Obviously nothing is 100 percent as objective as you'd like, but at least that's something you can do.

You can look into the glass door, you can do like G2, Gartner. I think it's Gartner Insights, all of these review sites and information is out there. Just do a little bit of research. Maybe I look at their customer's page. If you know someone who works at any of the companies there, reach out to them and see. The second part was when he talks about the failure. Just based on the LinkedIn alone, Kevin's resume is impressive.

It's just like the moment I read his LinkedIn profile, I immediately mapped to the Crossing the Chasm journey, just because it just seemed like he went through the chasm over and over again with multiple companies. I really appreciate the fact that he shared a story. You don't see the failure stories with any headlines or with any LinkedIn profile, you never know.

It's just something that people have to go through and it's like death and taxes. Failure is just a part of life. People just tend to forget if you keep like reading the tech crunch headlines or any other news headlines. It's 

Christian: also interesting, he said he has more failures than success. It seems like that, just one success makes up for many failures.

So as long as we continue pushing, even after failure, we will have success. And then we hopefully have ultimately a resume that looks like Kevin's. 

Trinity: I think you learn from the failures, right? I don't think you're going to get to success over and over if you never had any failures. I feel that it's, kind of, like ingredients. Like you make a dish, do you need ingredients, A, B, C, D, and failures? Just those ingredients. If you don't have any of those ingredients and you just hit it straight out of the park, I think that's just pure luck. And maybe you're lucky and you have it once in your life. So the third area is about the category creation part.

Everyone loves the Thinking Big book and then Category Creation by Anthony Kannada from Inside. Everyone loves talking about category creation, and then everyone thinks that their startup should be the new category. Maybe this is kind of obvious and already mentioned, but I feel like a lot of times people think of creating category is creating a brand new category that no one has ever heard of before people think about categories and they think.

This new thing that no one thought of before, but now that I talk to more people about it, read both books, actually in the third one, is the Obviously Awesome by April Dunford. The new category could be a niche within an existing category. Where you could be the winner. So like, say if you're competing, if you want to compete with Salesforce and CRM, don't come up with something completely different that no one understands.

Maybe you could be a CRM for financial services or something. Cause then that will give you a chance of, at least give the audience a frame of reference of what you're in without having to educate them so much about what this is. But then also, maybe you're so small that the competitors, like the big ones, the incumbents won't care so much that you getting that because that's not their space.

So that gives you a chance to grow. Then when you're ready and the timing's right, like what Kevin said, then you can expand to the next adjacent niche within that category and eventually kind of helping you crossing the next stage, and the next stage, to be a legitimate CRM player that's worthy of going head to head against Salesforce.

Christian: He talks about the first hundred days, and I think the important thing is that he said, that already starts before you actually have your job. I think the idea behind this is we always draw on between, let's say, the first three days of the first hundred days, how much is it listening and how much is it already like trying to add value there? I think he wants to get this jump start on the conversations where it's like, yes, obviously the first 30 days are about listening, about creating my hypothesis, but if possible, can I already, a little bit, establish myself, create a little bit of short-term value on small things.

Because even if I'm getting like, it's about getting information from everyone, from sales, from marketing, et cetera. I still have this outside perspective that as long as I know my limitations can be helpful in seeing things a little bit differently. 

Trinity: Are you going 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 And if you're looking for the ultimate revenue leader, Cheat Sheets, sign up to receive