Revenue Rehab: It's like therapy, but for marketers
Nov. 23, 2022

My Journey with Tyler Shields: Analyst, Investor, CMO

This week our host Brandi Starr is joined by Tyler Shields, CMO at JupiterOne. Tyler advises, guides, and operates high tech start-ups primarily in the B2B cyber security space. As a former market analyst, engineer, product manager, marketing leader,...

This week our host Brandi Starr is joined by Tyler Shields, CMO at JupiterOne.

Tyler advises, guides, and operates high tech start-ups primarily in the B2B cyber security space. As a former market analyst, engineer, product manager, marketing leader, and partnership manager, Tyler builds and grows businesses – in all aspects. He is a board advisor or board member at multiple firms and an investment advisor for multiple venture capital and debt firms and his experience includes starting, leading, and growing companies including JupiterOne, CA Technologies, Sonatype, Signal Sciences, Veracode, Symantec, LURHQ, Secureworks, and @Stake.

As a well-known leader in entrepreneurship and innovation in the cyber security market, and having spoken at many major industry conferences, his expert commentary has been referenced online and in print by publishers such as Rolling Stone, Bloomberg, Forbes, Reuters, and the LA Times.

In this week’s episode, the first of Revenue Rehab’s my journey series, Brandi and Tyler discuss his unique path to the present in My Journey with Tyler Shields: Analyst, Investor, CMO.

Bullet Points of Key Topics + Chapter Markers:

  • Topic #1 From Professional Cyber Security Hacker for Hire to Public Speaker [9:21] “I think there was a turning point for me, when I realized that hey, I know this content better than my audience” Tyler says. So public speaking was a natural progression; when you’ve created the knowledge that very few people have, you become more confident in your ability and in the benefit of doing public speaking.
  • Topic #2 How his Role as an Analyst Was Instrumental in his Journey [17:34] Tyler describes how these roles were key to taking him “to the next level of understanding how business actually operates at a strategic level and how to help guide executives”. You become informed in a way that helps C suite to understand their strategy and differentiators, he explains, as well as giving you a window into how both sides work, which is invaluable.
  • Topic #3 From an MBA to Investor, Advisor and Board Member [22:44] While his first advisory role was accidental, Tyler describes how it was his satisfaction in helping a company to do something that lead him to offer start-ups recommendations without charge. Which often lead to being compensated as an official advisor or invited to angel investing.

So, What's the One Thing You Can Do Today?

Tyler has one and a half things you can do today; the half is to be passionate about what you are doing. The ‘one thing’ you can do today says Tyler, is to start to figure out how you can be better than everybody else in your field and then leverage that differentiator, “almost consider yourself like a product,” says Tyler “leverage that differentiator to take you to the next level”.

Buzzword Banishment:

Tyler’s phrase to Banish is the expression PPL aka ‘product led growth’.  “I think it’s a false term”, shares Tyler.  He’s started swapping it out with PPL, Product Led Leads, which he says is a more accurate description of the PLG approach.


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[0:05] Intro: 

Welcome to Revenue Rehab, your one stop destination for collective solutions to the biggest challenges faced by marketing leaders today. Now head on over to the couch, make yourself comfortable and get ready to change the way you approach revenue. Leading your recovery is modern marketer, author, speaker and Chief Operating Officer at Tegrita, Brandi Starr.

[0:34] Brandi Starr:  

Hello, hello, hello and welcome to another episode of Revenue Rehab. I am your host Brandi Starr, and we have another amazing episode for you today. I am joined by Tyler Shields. Tyler advises, guides and operates high tech startups, primarily in the b2b cybersecurity space. He is a former market analyst, engineer, product manager, marketing leaders, and partnership manager. Tyler is also a board advisor and board member at multiple firms and an investment advisor for multiple venture capital and debt firms. Tyler's expert commentary has been referenced online and in print by publishers such as Rolling Stone, Bloomberg, Forbes, [inaudible 01:21] and the LA Times. He's also contributed to multiple television and radio interviews for both the National Public Radio and the BBC. Tyler, welcome to Revenue Rehab, your session begins now.

[1:37] Tyler Shields:   

Wow! What an introduction. It's almost embarrassing to have it read out like that, but thank you.

[1:43] Brandi Starr:   

I am always impressed by you know, the guests that I have, and I learn something from the bios. So the fact that you've been in Rolling Stone and Bloomberg, I feel privileged that you have come to the couch and are joining me on Revenue Rehab.

[2:00] Tyler Shields:  

Thank you so much for the invitation. I appreciate it.

[2:03] Brandi Starr:   

Awesome. So before we jump in, I like to break the ice with a little woosah moment that I call buzzword banishment. So tell me a buzzword that you'd like to get rid of forever?

[2:18] Tyler Shields:   

Well, you're probably going to be surprised to hear it, actually I'm sure most of your listeners will be surprised to hear it. But I think we need to get rid of the buzzword of product led growth because I think it's a false term. And it only works in certain magical scenarios. And it's, I think, a Nirvana that too many marketers shoot for when it may not be right for their business.

[2:44] Brandi Starr:   

Okay, I can definitely support that. I can say, overall, I believe in the PLG model, but I do agree that it has kind of become a hot thing that it seems like everyone needs to chase PLG and you know, it's not going to be right for all companies.

[3:05] Tyler Shields:   

That's exactly right. I don't dislike PLG. I love PLG in the perfect circumstance and I don't think enough marketers understand what it takes to have PLG be successful and what the circumstances really are for it to be successful.

[3:20] Brandi Starr:  

I see a lot of people that are trying to do this hybrid thing where it's going to be PLG, but then we'll have sales to support the later side. And it's like that that's not what that means.

[3:32] Tyler Shields:   

And actually what I've what I've started calling it as PLL- Product Lead Leads. And that's okay, go ahead and create product lead leads, have your product get out there, get people interested in it, and then sell to them. That's totally fine. But it's quite a bit different than a pure PLG approach.

[3:46] Brandi Starr:   

Yes. And I won't go down that rabbit hole, because we could definitely spend the next hour talking about what's wrong with PLG for sure. But I do like the term PLL, so I may have to dig into that separately. 

[04:00] Tyler Shields:  


[04:01] Brandi Starr:

But now that we've gotten that off our chest, tell me what brings you to revenue rehab today.

[4:08] Tyler Shields:   

I think what brings me here mostly is to talk about how every marketer and every market leader can have a unique journey. And you don't have to come up through traditional approaches to marketing to become a C suite executive in marketing. Right now I'm the CMO at a cybersecurity startup called JupiterOne. We're growing fast and my history, yeah, the last handful of years has been in marketing, but I didn't come up through a marketing path. I came up through a very different approach to marketing which is much more I guess, strategic and engineering centric, and then transferred and got that into a marketing type of role.

[4:51] Brandi Starr:

Awesome! I am looking forward to digging into your journey. And so I'm really excited; this my journey series was put together because figuring out their path is a hot topic amongst current executives, as well as those that want to become executives. And every time I meet people and hear their stories and how their career has progressed, I'm always so intrigued and learn something, so I wanted to bring that to our listeners. So you are the first journey that we are digging into. So thank you for letting me figure out how to pull that out of you live here on Revenue Rehab. So tell me, I will start with a where did your career begin? And was it on purpose or did you fall into it?

[5:49] Tyler Shields:   

It's a great question. I apologize. If I have the sniffles today, I'm coming off of a bit of an illness. So apologize in advance for that. But I would say I largely fell in to every phase of my career. And the reason why, and at the end, you asked me to come up with one recommendation for everybody. And my recommendation will play directly off of this fact.  I've always just done what I enjoyed doing. And I chased that. I always wanted to be happy day to day working on whatever it is I'm working. And if I was no longer happy, I found another way to be happy at that job or at a different job or at a at another stage of education. So actually, I came up as a cybersecurity professional hacker for hire, that's where my roots are. I started doing that before I even graduated from undergrad as a side business. Before it was even like a thing that you could barely legally do, I was doing it. So I came up through those ranks, became an engineer with a computer science background. From there, I got my master's degree in computer science, ended up being in an R&D side, became a speaker at different conferences on cybersecurity expertise and depth. And then kind of flipped things on its head, went back to business school, got a second master's degree in MBA, and decided I wanted to build businesses. That was my goal. It was never to be a CMO. It was to build businesses, whatever that meant. And so ended up being an analyst for Forrester Research, and that was my transitional phase between engineering and cybersecurity deep expertise. And where I ended up becoming an investor, CMO advisor to mostly cybersecurity related startups, because it's all anchored in that understanding of the technology depths that I have. So I've always just followed what I thought would be fun to do next. And that may not work for everybody but it certainly did for me in my career. 

[7:49] Brandi Starr:   

I do love the approach of really trying to follow what you enjoy most, because I mean, you know, you think about the number of hours and the percentage of our life that we spend at work and thinking about work and in school to lead to a job. It's like, there's a huge amount of time there. And so if you're doing something that makes you miserable, or that you're even lackluster about it's like you're investing a huge portion of your life to not enjoy it. So I love that as a driving factor.

[8:29] Tyler Shields:   

And I would say like, the transition periods were funny for me, because usually it came down to the fact that I was stagnant in learning. So I did a lot of cybersecurity hacking for higher penetration testing offensive security stuff, and then got bored with that. I said okay, I'm going to, I'm going to go back to school. My twist was always well, if I'm not getting enough out of my employer, to make me happy, how can I figure it out for myself to make me happy? How can I continue to grow? And for me, that was, alright I'm going to go back to school and get a master's degree in computer science. Do that for a while, got tired of that, okay, I'm going to go back and get an MBA, do that for a while. So for me, it was always education. I don't think I can pull the trigger on a PhD but trust me, I'm pushing 50. And I thought about it, I've thought about going back and doing the PhD thing. But I don't think I can pull the trigger on that. That might be a little too ambitious.

[9:21] Brandi Starr:   

So I want to back up a little bit. So professional hacker for hire, turned engineer, turned R&R. I can see a very logical path there. those skill sets are very complementary. And then you became a speaker, and I want to talk a little bit about that because generally people who are very technology or engineering oriented, tend to not like to be out front, aren't great at being able to command the stage. So I want to hear a little bit about how you became a speaker, and how you were able to be successful in that?

[10:02] Tyler Shields:   

Actually there's a couple of fun stories in that. What ended up happening was I was doing a bunch of deep computer science research for a company called Veracode at the time, around mobile security and reverse engineering of different binaries and applications and trying to understand if there was malware malicious code inside the applications. I did a bunch of work for them. And then I started going on the lecture circuit on the back of that work based on talking about the research that I did. So it's very academic style of speaking right out of the gate. It's funny, the first time I actually did any public speaking, was at a conference way, way back. It was much earlier than that kind of phase we're talking about. And I remember that my first speaking engagement, I went up, and it was probably close to 800 people in a room, 700-800 people in a room was a massive ballroom at a conference in New York City. And I remember walking up on stage, completely blanking out; I don't remember from the time I got on stage, the time I got off. But when I went back and watched the video, I literally read from a piece of paper, my speech word for word. It was the worst speech and experience ever. I got off the stage and one of my friends was like, good job. And I was like, go away! That was awful! I don't even remember any of it, it was so bad. But I think there was a turning point for me, where I realized, hey, I know this content better than my audience. And when you kind of make that leap, when you're like, hey, I wrote this content, I created this research, I created this knowledge that nobody else has or very few people have, you become a lot more confident in your ability to speak about it. And I've also found that when you're doing public speaking, I think there's a normal curve almost to it, where you get better and better and better and better as you speak the same talk at different conferences and events, and then you hit a peak where you're so bored with the content, you get worse and worse and worse. And so I definitely had that curve. But I would say the public speaking became more natural to me, as I became aware that people cared about the content, and that it just became kind of a natural flow for me, which is funny, because I'm a natural introvert. I actually don't care for public speaking, it drains me. And I intentionally got out of it for quite a while, and I haven't done much public speaking in a handful of years.

[12:24] Brandi Starr:   

And I know I have always heard that introverts make great speakers, because they tend to prepare more than... I'm naturally very extroverted. I started doing public speaking in middle school. And I have had scenarios where it's been like two days before, and I'm like, oh yeah, I should figure out what I'm saying. And so it is a little bit more for me of like, I'm going to take the stage and I'm going to wing it, and it's still going to be amazing. And so that is sort of the downside to extroverted speakers is there....

[12:59] Tyler Shields:   

I would argue, I would argue you're capable of that because you know your content so well. 

[13:05] Brandi Starr:  

That is true. 

13:05] Tyler Shields:

In your heart, you created it, you truly believe what you're speaking about. And so that actually happened for me too. Early on, I would prep big time as an introvert. And then I got to the point where I just like, hey, I know this content so well, because I built all the research, I built all the stuff behind it, that I could actually not even prep, just walk up on stage, have a handful of slides ready and talk about it for an hour. So that's also something that I think, as you become a more frequent speaker and more recognized, you become just more and more confident, you can actually kind of ad lib a lot more. Today, I pretty much will only do conversational like panels and moderated type stuff because I love the conversation, it's so natural for me because you're just speaking from the heart.

[13:46] Brandi Starr:   

And those are a lot of times for the audience the most insightful because they tend to go where the conversation goes and not in a planned path. So you talked about education, and when you got to the point where you recognize that you wanted to build businesses, that you went back for your MBA. And I know, this is always a hard decision, especially when you're so far into your career. It's like, do I go back to school? Do I have time to go back to school? And I've known a number of people as they've moved up have been in that sort of crossroads of, do I need this education? Is it worth it? So talk about your decision to go back for your MBA?

[14:34] Tyler Shields:   

So I went back twice, right, I went back to get the Masters in Computer Science then I went back to get the MBA. When I did the masters of computer science, I just felt I needed something to break through the knowledge barrier to get to the next level. But I don't think everybody needs that. I know tons of people that do not even have undergrad that can do fantastic computer science style research and speak on the lecture, so you don't need that. But for me, I think it was a formal education that helped me internalize all the concepts. And I will say that later on the investing, the building businesses all of that I can't do what I do today without the underpinning of computer science. Because the way I approach business is actually built upon, does the technology do what you think it does? Does it actually technically work. And that allows me to make really strong investments, that allows me to make great decisions understand differentiators and companies, all of those kinds of things. And it's the underpinning of the computer science that helps me do that. Now, I also couldn't do that, without the MBA, to understand how the finance works, to understand how the how the go to market engine might work, to understand what I described as a complex system of a business. How all of those cogs you turn one they all turn. And so for me, I think the formal education path was required, because it's just how my brain works. But I wouldn't say it's mandatory, I think you can learn, especially in today's world with so much information online, I think you could learn it all self-taught. But I needed that formal education to actually get to that point.

[16:09] Brandi Starr:   

Okay, and that that is a good -- I mean, even thinking about I've got four young adults who all had to make the decisions on whether they were going to college or not. And I had to have that conversation with them to say, it's not mandatory. You can get where you want to be with or without it to a certain extent. And so it's interesting that you have that same perspective, because I have talked to people who have reached the VP level, and they're like, I feel like in order to get into the C suite, I need to go back for a masters. And I'm like, like, but do you? 

[16:47] Tyler Shields:   

It's such a tough discussion, because there are certainly glass ceilings that you'll bump into without the credential stamp. I'm not going to sit here and say that you can easily get in if you don't have it. Now, you got to understand my world is a very unique world. I'm not in like retail or consumer packaged goods or anything like that. I am in cybersecurity, which is a very unique space where one can self-differentiate by their technical background. So that allows you to break through some of those ceilings, I think, occasionally. But if I go across the board, excluding the founders of the company, which don't always have advanced degrees, excluding the founders, most C suite do have advanced degrees. And I can understand why people would think that you're bumping into a glass ceiling, because it's harder to get hired.

[17:34] Brandi Starr:   

That's a great point. So let's talk about being an analyst. In my world, as a marketer, there is a little bit of a love-hate relationship with analysts. So tell me about being on that side of the fence and what that's like and how you felt, what made that the right, next move for you?

[17:58] Tyler Shields:   

Sure, yeah, absolutely. I think everybody had probably can say this. But there's certainly a few jobs or roles or positions you've had in your career that are instrumental in advancing you to the next level. You can usually pick out oh my gosh, that one was super important. There was a consulting firm I worked for called At Stake when I was in my young 20s, instrumental in jumping me to the next level. I would say that Forrester Research was 100% instrumental and taking me to the next level of understanding how business actually operates at a strategic level and how to help guide executives. Now, I want to comment on the love-hate stuff first, and then I'll talk about what I got from it. I understand why it's a love-hate, because it's super easy to think that analysts are influenced by money and biased and bought and paid to play and some 100% are, I'm not going to say that there aren't those out there that are like, hey, give me 80 grand, I'll write a report that says you're awesome. They definitely exist. Now if you get a reputable firm, and you get reputable analysts within the firm, the individual analyst is key. They will write what they truly believe, regardless of where the money is coming from for the business. And that's how I prided myself. And when I was an analyst at Forrester, I wrote predominantly on startups, because that's what I was excited about, younger companies that were doing innovative things given my technology background, that's where I did my writing. It didn't matter who was paying Forrester what. So I think it's an individual analyst issue. And you got to make sure you find the right analyst for your market. Now, from my personal value, it took me from hey, this guy talks about reverse engineering binaries nerd nerd nerd nerd to a wait a minute, he can also talk about how that impacts the business and what's the strategic direction of Citrix or VMware or Mobile Iron based on the technologies at choice. And that era is when I was in Rolling Stone, BBC network, all of those things you talked about that were mildly blushing for me at the beginning of this conversation. That's where all of that recognition came from. It's in that era I got a chance to speak on topics that I was researching and analyzing. And the cool thing is you never lose that knowledge on how to do it. And as a matter of fact, right now, I'm starting a sub stack as we speak, which is going to be my musings, my thoughts, my analyst stuff; I'm not going to get paid for it, I'm just going to put it out as a creative outlet for myself as a basically a freelance analyst for nothing.

[20:35] Brandi Starr:

Awesome. So if someone is listening to this, and they are wondering if going down the path of becoming an analyst might be for them, what thoughts do you have in how to self-evaluate whether like, the good, the bad, the ugly? How do I know if this is a path I might want to take?

[20:58] Tyler Shields:  

It's a good question actually and I've helped a couple newer analysts who were thinking about the role, who approached me said, hey, can you talk to me about it. I've actually took one of them out to lunch locally here and we had a long discussion about it. And I think the good is, it's a huge jumpstart for your career. You're going to sit with every senior executive, every suite C suite of the markets you cover, you're going to get to sit with all of them. You'll go face to face with them, you'll help them understand their strategy, their differentiators and you will help enterprises who want to understand what products to buy, how to buy them, et cetera, you'll get visibility into both sides of that very, very intimately. But what makes a good analyst is someone who's passionate about that market. If they're just going to sit back and be like, hey, I'm just going to write stuff and punch the clock, then never be a successful analyst. You have to have strong opinions. And I always say I love the phrase, strong opinions weekly help, because I want the feedback. I want the commentary I want to learn and that's what makes a good analyst. Listen, as an analyst, you're going to put out tons of future predictions, this market is going that direction, this is going to happen that direction, you always get to get out of jail free card as an analyst because you just bring up the ones you're successful with. You ignore the losers. But in reality, the losers the one you miss, like, I predicted mobile security would be the biggest market in history. It floundered and died, it went nowhere. But I learned from that why.  And now in future statements, I won't make that same mistake. And so I think you have to be opinionated, you have to be able to take feedback, both good and bad, because you'll get ripped by vendors that you say are bad, they're going to rip right into you. So you have to be thick skinned. And you have to just think of it as a passion project where you tell the truth. And if you stick behind that, I think you can make a good analyst.

[22:44] Brandi Starr:  

Awesome. What's next is a common topic. And when people don't have insight into it, it's like, oh, maybe I shouldn't try that, but that always helps. So let's shift gears a little bit, because I know that you are also an investor, and an advisor and sitting on boards. So let's talk about that. Was that something that you sought out to do? Did opportunities kind of pop up and you said what the hey! Tell me more about how you got into that side of business?

[23:21] Tyler Shields:   

It's a really, really great question. The very first advisory role that I ever took for a startup was accidental after I came out of being the analyst role and went into a head of marketing role actually, was right out of analyst. A company reached out to me and said, hey, can you help us get into the Forrester Wave? Can you help us understand the process better, etc? I was like, yeah, sure. And they're like, we'll make you an advisor to the company, to help advise us on this one thing. I said okay. And that was my very first one, so it was kind of accidental. But from there, it was kind of like I enjoyed the work of helping a company do something. And what it ended up morphing into generally, was helping a company devise what their go-to-market should look like, given a certain technical capability. Because there's not a lot of people out there that that can really talk about the go-to-market, the marketing, the revenue, the business side of it, and get super deep and talk about the bits, the bytes, the assembly language, there's not a whole lot of people that can make that glue. And so what I started doing was just, as I got introduced to new startups, through different friends and stuff, just offering free of charge, karma based, what can I do to help you? And that kind of got me into advising a handful of companies that were like, well, you can do this. I'm like, okay, let's go. Like you don't want anything for it. Nope. I'll meet with you guys every other week for an hour help you figure it out. Well, fast forward six months of doing that, and they're like, hey, we're going to make you an official advisor. We feel bad we're not paying you for this. Things like that started happening to me. And on the back of that it started becoming hey, we're going to run an angel round. Do you want to get involved in the angel round? Yes, I do. Let's start getting involved in Angel deals. And so it really came from just wanting to help others 100% Karma based is where all that came from.

[25:11] Brandi Starr:   

That's beautiful. And when you do something really well and when your intentions are in the right place, I do think what happened to you is what happens. People are like yeah let me give you my money, as opposed to some people who chase the money and think like, oh, being an advisor is like a whole extra stream of income and really go into it for that. Really interesting. And so the last area that I want to dig into, because CMOs are our primary audience, so I would be remiss if I did not dig in more around your journey as a head of marketing. What have you seen as the biggest challenge as you have been leading marketing organizations?

[26:04] Tyler Shields:   

Wow, that's a really good question. Because I can answer it in so many different ways. I can answer it in the like stage zero way, like what's the biggest challenge when you're first starting a startup and gaining traction. And I would say the hardest thing there is creating enough of a buzz and content that gets people excited. That's hard to do when you have no brand. And this is where the analyst background comes in handy for me, because I can get in there, write the content that people find interesting and start the buzz train going. And so that's one of the reasons why I think I kind of fell into the head of marketing role was the kind of that PMM content creator capability. And I think that's hard to find. I find that a lot of these younger startups anyways, have trouble finding people that can write at a talented level, the type of content that will generate an audience and buzz and following to a new company or a new product. So that's kind of one answer to that. The second answer is the scale problem. The scale problem is totally different. And at some point, you go from, hey, I'm the person creating the content, the engine, all of the hands on tactical, to hey, I'm the person that has to lead and hire and mentor and grow. And it's two different stages and two different massive difficulties when it comes to growing the organization. It's hard to do both. You're usually better at one than the other. I don't know, talk to the people that I've hired and see if I'm a good leader, but I like to think that maybe I'm okay at both. But I think those are the two problems you run into.

[27:38] Brandi Starr:   

Okay, and I know, from talking to some heads of marketing that are at those stage zero, those early stage companies where they are the head of marketing, but for the most part, they are the marketing team, one of the things that I hear is the struggle in not getting stuck there. I've talked to people where they're like, yeah, I'm at my fifth stage zero company, there's some volatility there from a career perspective, and they find it difficult to make that jump into more established or even larger company. Any thoughts or advice on why that happens or how people cannot get stuck, just being that team of one?

[28:30] Tyler Shields:   

Are you are you specifically talking about the what I call the two year bullseye, the two and a half year Bullseye meeting your stage zero startup marketing guy or gal, two to two and a half years later, you're no longer there no matter what? 

[28:43] Brandi Starr:


[28:44] Tyler Shields:  

I would say, if you're good at that, and really good at that, there's nothing wrong with saying that's what I do. And every two and a half years going and doing another one, getting a massive equity jump, being successful at that next one, and doing it again. However, if that's not something that excites you, and you consider that boring, you've done your third one, you're like, I don't want to do this anymore, you almost have to bite the bullet and go back, go to a big company. Now I think for me, I get stuck in that role. I'm seen as the zero to let's call it 20 million ARR guy. And that's because that's what I'm good at. And that's also because I did not come up through traditional marketing at scale. I didn't work at a marketing role at Uber or Airbnb or insert massive tech company here. I came up as an engineer who learned to build marketing GTMs from the ground up. But I've never actually scaled one past 20 million. So for me, if I wanted to go do that, which I kind of don't, but if I did, I would go back and say, hey, give me some kind of super senior like VP or something at one of those companies and get that experience on the resume. I think anybody can make the move they want if they push themselves into that role, and stretch their capabilities and spend some time doing it, you'll be able to grow there too.

[30:03] Brandi Starr:  

So what I'm hearing is sometimes that we need to step back, in order to be able to step forward.

[30:09] Tyler Shields:

I wouldn't even say it's a step back. I would argue that the zero to 20 million kind of roles like I take, you're probably getting paid the same amount as a senior director or VP at some of these massive companies, because they're paying so high. And you're at a startup that's more equity driven. But that being said, it's more about again, following what you're passionate about, if you're passionate about growth and scale at the larger size, find a way to go do it. And I think anybody can figure that out if they put enough passion and time into their network and looking for job openings and pushing their way into that kind of role. You can do that too. I've always throughout my entire career, said this is what I want to do next and I went and got it. And that's what I would suggest to somebody who might be stuck in that 0 - 20, who doesn't want to be there.

[30:53] Brandi Starr:

I love it. Well, talking about our challenges is just the first step and nothing changes if nothing changes. So I like to give action items. And in traditional therapy, the therapist gives the client homework. But here at Revenue Rehab, I like to flip that on its head and ask you to give us some homework. So what one thing one action item would you give to our listeners who are trying to figure out how they build that career path from wherever they are to where they'd like to be?

[31:30] Tyler Shields:

I'm going to cheat and give you one and a half. The half is be passionate about whatever you're doing. And you can hear it from me. I was passionate about tech, I was passionate about business, I was passionate about doing the karma thing. Passion, Passion, passion, be passionate about what you're doing. But the one thing I will tell anybody is that there's nobody that can stop you, if you want something, you have to figure out what that next step in that path is for you. And I would argue, go figure out how you can be better than everybody else in your field. And leverage that differentiator, almost consider yourself like a product, leverage that differentiator to take you to the next level. I'm known as the person who can get into the weeds of the tech and can market it in cyber. That's my differentiator that not a lot of marketers have, what's your differentiator. So my homework would be go figure out what your differentiator is, and then leverage it to success.

[32:26] Brandi Starr:

Perfect. I love that. I have thoroughly enjoyed our discussion. But that's our time for today. But before we go, how can our audience connect with you?

[32:39] Tyler Shields:

I'm at TXS which are my initials, Tyler no middle name Shields TXS on Twitter. You can catch me on LinkedIn. If you reference the show, when you connect with me on LinkedIn, I will actually connect with you. Because I don't generally connect with random connections. But if you say you saw me on Revenue Rehab, I'll be happy to connect with you and chat with you on there. Catch me on Twitter, you can always email, happy to respond to inquiries.

[33:03] Brandi Starr:  

Awesome. And I know that you also have a podcast. So go ahead, I like to leave room for the shameless plug.

[33:10] Tyler Shields:

Yeah, I have a couple of them. So I actually am a cohost on a show called Enterprise Security Weekly, which is done every Thursday. And then I currently co-host a show called Cyber Therapy, which is funny given the given the content here called Cyber Therapy, which is hosted by JupiterOne. is the company where I'm a CMO. So you can always catch me at either of those podcasts as well.

33:32] Brandi Starr:

Awesome! We will make sure to leave both of those links in the show notes. And for anyone who is listening who is wanting to continue learning more about others career path, I encourage you to go back to episodes nine, where we talked about Uncoupling as a CMO and then as well as Episode 20, where we talked about some other CMO Exit strategies. Tyler, thank you so much for joining me today. Thanks, everyone for tuning in. I have enjoyed my conversation with Tyler. I can't believe we're at the end. We will see you next time.

[34:12] Outro: 

You've been listening to Revenue rehab with your host Brandi Starr. Your session is now over but the learning has just begun. Join our mailing list and catch up on all our shows at We're also on Twitter and Instagram at Revenue Rehab. This concludes this week's session. We'll see you next week.


Tyler ShieldsProfile Photo

Tyler Shields


I advise, guide, and operate high tech startups primarily in the B2B cyber security space. I'm a former market analyst, engineer, product manager, marketing leader, and partnership manager. In other words I build and grow businesses - in all aspects. I'm a board advisor or board member at multiple firms and an investment advisor for multiple venture capital and debt firms.

My experience includes starting, leading, and growing companies including JupiterOne, CA Technologies, Sonatype, Signal Sciences, Veracode, Symantec, LURHQ, Secureworks, and @Stake. I am a well known leader in entrepreneurship and innovation in the cyber security market, having spoken at many major industry conferences.

My expert commentary has been referenced online and in print by publishers such as Rolling Stone, Bloomberg, Forbes, Reuters, and the LA Times. Additionally, I've contributed to multiple television and radio interviews for both National Public Radio and the BBC.