The Next CMO Podcast: Kyle York, CEO and Managing Partner of York IE


Episode Overview


TheNextCMO’s latest podcast is with Kyle York the Co-Founder and CEO of York-IE. Kyle works closely with entrepreneurs and investors to help them realize their shared ambition to build good companies, create new jobs, grow generational wealth and impact the world. In this podcast we discuss Kyle’s wealth of knowledge in the technology industry, his GTM strategy, York-IE’s unique business model, how the pandemic has impacted his investment approach, and how to recruit executive talent.

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Full Transcript

Kelsey Krapf 0:00
Welcome to the official podcast of the next CMO hosted by Plannuh. The next CMO is a thought leadership podcast for those that are CMOS or want to become one. My name is Kelsey Krapf, and I’m the senior marketing manager.

Peter Mahoney 0:14
And I’m Peter Mahoney, and I’m the former CEO of Plannuh, and welcome to the next cmo podcast.

Kelsey Krapf 0:34
For week, we have Kyle York the co-founder and CEO of York IE, Kyle works closely with entrepreneurs and investors to help them realize their shared ambition to build good companies create new jobs and grow generational wealth and impact the world. How are you doing today, Kyle?

Kyle York 0:51
Hey, thank you for having me.

Peter Mahoney 0:53
Well, well, Kyle, it is it’s awesome to have you and I was perusing through your your bio the other day on your website. And I reminded me of your I don’t know if you call it lack of focus or ability to handle multiple things at the same time. But you’ve done a little bit of all of it. Right. So you you were sort of a growth stage guy who grew dine to a pretty big company hundred million dollars? I think

Kyle York 1:25
that’s right, yeah.

Peter Mahoney 1:26
And then sold that to Oracle. And then you were in, by the way, if you know, Kyle, you wouldn’t picture him as central casting as the Oracle executive. But you were an Oracle executive for a while I was and then you use you started, that you started your IE, and we’re gonna ask you to talk about that a little bit more, because it’s a fascinating combination of things. And then on top of that, you happen to sit on the board of your multi-generational family business, York athletic, and you’re a shoe guy. So so you, you got a little bit of while. So before you tell us a little bit more about your work, ie I’d love to understand of all of those diverse roles. And you probably have others, like your dad and your friends, things like that. But if you’re professional roles, which which one of them stands out as the one that you like the most.

Kyle York 2:21
Yeah, absolutely. So I mean, first and foremost, say, I am your stereotypical entrepreneur. You know, I grew up in a small family business, that was actually a second-generation family business was a sporting goods retailer in Manchester, New Hampshire. And before that, it was actually a footwear manufacturing company started in 1946. So multigenerational involvement in business, but involvement in business around sports also grew up playing sports. So it’s very competitive. I played four years of college football, family and wall fam not far from the folks. So I’ve always sort of been involved in entrepreneurial endeavors. And what I’d like to call it all as a portfolio approach to business, you know, the, the way in which my parents built their business as a kid was actually the outside world look like one company, but it was actually four or five companies, you know, there was a real estate company, they on their property, the property was right across from the now Southern New Hampshire University arena and Manchester. So he had a parking lot business for me. So parking after hours, they had their screen printing and embroidery business that did uniforms, you know, hats, all that for? And then they had their team and retail businesses for sporting goods. So where do you go to buy all your bats for your baseball team or all your all your equipment for your basketball team, all that. So it was actually multiple businesses in one. And it was interesting how one played off the other. And I thought to myself, when I got my career going, like, if I could figure out how to do that, you know, blind, my competitive spirit, my entrepreneurial nature, obviously have anchor anchor things to ground me and keep me focused. So it isn’t a lack of focus. that that would be a heck of a lot of fun. And so I think of it as almost the modern-day manifestation technology and startups that I grew up with. So it’s all I know.

Peter Mahoney 4:16
Oh, that’s, that’s awesome. I think of you as a renaissance man. put it that way, right. You’ve got this nice, incredible diversity. And I think it’s one of the things that makes your your background compelling for your clients is that you’ve seen a little bit of everything. And it’s funny, before we started, we were chatting about the fact that you have vertical integration because you guys actually have you own your building for your guy as an example. But your your family business is almost like horizontal integration, because literally, you’re just branched out pretty much.

Kyle York 4:48
I mean, I think when you think about me, I mean, my core job is the CEO and co founder York I, that’s when I wake up every morning. That’s what I think about in New York. It is now it’s a next generation investment firm. Powered by market data and analytics and focused on growth and go to market, right? Like we, we have a lot of go to market experience in software businesses, we have lots of investing experience software businesses, we have lots of governance experience in software businesses at you know, Oracle scale all the way down to the to person and their dog startup, right. So, at core, that’s what we do. And the majority of my day to day is in software technology and infrastructure, vertical SAS, you know, cut up and down the stack. And that’s the team I manage and run, we’ve packaged a lot of the more consumer brand media oriented stuff under the York Creative Collective, which I’m fortunate to have a brother and good friend. And as my older brother, I’d like to make sure people know that as well, who runs a marketing agency and runs your creative collector, so he’s the CEO of that. So all the media consumer-oriented brands are, you know, packaged under there. And then, you know, we have our real estate community affair. So really, it’s it’s kind of three things, even though it’s maybe all in all, like upwards of nearly 100 companies that we have a stake in. And I always talk about it as an engagement matrix. You know, it’s where do you put your your time? Where do you put your capital? And, you know, not every single company we work with is in the upper right quadrant of the time on the y and capital on the X axes. It’s it’s diverse across the whole portfolio. And certainly, some companies and through COVID times have certainly demanded more attention. You know, but other times, you know, I think the portfolio approach when times are good, it’s, it’s a heck of a ride. You know, so it’s been an interesting, it’s been an interesting thing to get this thing built, after obviously, the great foundation of my operational experience at Oracle and, and died before that, which, you know, makes it all possible.

Kelsey Krapf 6:58
So how does your job of a marketing leader, you know, change in those different environments, and, you know, all of these things that you have going on?

Kyle York 7:06
Yeah, I mean, if I look back to my early career, you know, as a marketing major at Bentley, and I ended up first job as a marketing, jack of all trades, and a start up, you know, it was basically everything from content to demand Gen to events to really what they really were trying to tell me to do is drive damn leads, right. So I was doing a lot of even BDR level work running our own our own captive conference, that was for a company that sold as a vertical SAS business in the K to 12 private school space. So if anyone on the on the on the line listening, you know, went to private school where the kids go to private school, or, you know, that’s they probably ran the software, this company, that company eventually ended up selling the Blackbaud. But, you know, it really taught me the landscape of like doing marketing and sales and go to market in a startup. And it was such an amazing fertile ground to learn. Because, you know, in one instance, I’d walk into a school that just got a $40 million gift from their board member, Bill Gates at the lakeside school north of Seattle. And then the next day, I’d go to a month of score, sorry, school and Massachusetts, with a kindergarten teacher who ran all the technology decisions, right? So you really learned how to market broadly to all levels of technology, experience, and scale and competence. And you know, would have to adapt and adjust on the fly, especially in those face to face or I guess back then I don’t know what it was WebEx or some other version of zoom back then. So you know, it started there for me, which gave me kind of the lens of the world that I think it’s just an amazing learning experience. And then through dine, me we did, we specialized in the DNS, such as the domain name system, became the world’s leader in the DNS and being a managed cloud provider of DNS. You know, our biggest site, I wear t shirts all the time, you know, used to be printed at my dad shop before he retired. But, you know, we had a campaign called DNS is sexy for many years. And, you know, for those who didn’t know what it was, it would make them ask you what DNS was. For those who did, they’d say, Yeah, right. It’s not really sexy, come on, and then and then you’d start to talk about actually, that Internet Protocol is kind of cool. And you can do a lot of really unique tricks with that technology. And, and so you know, it became this that fertile ground of learning how to market you and talk to anybody depending upon where they are on the spectrum all the way to how do you take something that no one understands and build a brand around it and scale that to all of a sudden at Oracle Oracle is like the number 17 most recognized brand in the world. I don’t think I don’t think everyone knows what they do necessarily, but it is it is a household brand name. Where there it was actually, on how do you market and evangelize attracts Information and that Oracle is actually becoming a different company than maybe you remember. And whether that be technically you know, a database company or reputation only a company with the bazillion lawyers, it’s gonna crush your soul. You know, those things are the things you had to navigate are the operators Tick Tock very different. Yeah. And now they operate Tick Tock which is, you know, an interesting an interesting so

Peter Mahoney 10:24
so now my my youngest is 19 knows what Oracle is. Those are the people who who kind of bought but not really Tick Tock it. So it’s it’s amazing how that happens.

Kyle York 10:38
Yeah, it is. And I mean, I, I’ve explained that the people that that is a there, whatever the mechanics of the DLR, they’re, in essence, their COC is quite high their customer acquisition costs to acquire Tiktok that is purchasing a customer. But it’s also purchasing a, a, a different way to look at the business, right? No one would have thought, the tiktoks or the zooms of the world will be running on Oracle Cloud infrastructure and the days of Azure and AWS and Google Cloud compute Google Cloud Platform. So you know, it’s, you know, it’s taking real heavy muscle deal prowess, and basically saying, how do we use that to our advantage to reshape our brand to the world? So yeah, I have this experience that very few have from like, your niche, vertical SAS startup to homogeneous infrastructure, niche product company to global scale, Oracle Cloud, who, you know, they run E, RP, human capital management, database infrastructure? I mean, people don’t even know they own MySQL, they own Java. I mean, it’s like, it’s it’s a such a behemoth. You know, and I think bringing those lessons together to sort of Manifesto, I believe, you build a brand, a sustaining brand for the next, you know, 2030 years, in startups today, and private companies today, I think has, you know, brings a lot of value to to those entrepreneurs and a lot of perspective that, you know, and a sequencing perspective, like a time horizon perspective that I don’t think a lot of people have. Yeah, I think

Peter Mahoney 12:11
that’s, that’s right, you do have this uniquely, voluminous experience, when it comes to just the diversity of the go-to-market that you’ve seen from consumer-related stuff, to, to broad enterprise stuff to big brand stuff, and everything in between. So it is you, you know, as with the investor side of you, figuring out go to market is probably the one key, that’s the hardest thing and the most important thing for for companies to get beyond sort of their early stages to become a sex successful company. So how do you take this broad diversity of stuff, and figure out when you’re coaching these companies how to apply the right kind of go to market techniques to solve their specific problem.

Kyle York 13:04
So totally. So I think the two, I could bucket two types of companies that we talked to, yeah, the one company with the biggest vision you’ve ever heard, to boil the ocean and attack a market opportunity, with no execution plan to get there. Right, that’s bucket one. bucket two, teeny, tiny vision, super focused ability to execute, but no total addressable market, and no scale to the company opportunity. And literally, like, every day, when I talk to somebody, I can bucket them in one of those two categories. It’s the rare company, you can, you know, talk about a vision holistically, and then give you a backwards plan with milestones all the way back to Day Zero, where we are today. Those are the companies that end up being the companies you really want to back or you really want to consult for advisor get involved with. Because at the end of the day, it’s it’s opening up when you hit milestones for startups, it’s about opening up the next opportunity. And this is, you know, everyone, you know, always talks about this, but there’s no perfect up into the right experience to the startup house. So what we really do is a lot of times we dilute this and it will be called our business strategy messaging hierarchy exercise. A lot of times it gets a little bit of bad rap, especially to technical founders, when we first start talking to them. It’s like I’m gonna work on messaging like us is so fluffy. But really what we’re trying to do is distill down what the heck are actual strategies is long before you should be doing a DAC or building a website or tactically executing your social strategy or your content strategy or demand Gen programs or event strategy. Like you got to actually know the vision know the mission. Know your descriptors, know your taglines understand your boilerplate, your elevator pitch, not just to throw in the About Us section at the bottom of a press release. But who are you what do you do? How do you do it? Who do you do it for? How do we get Get in touch and actually have some contact with you. And bring that all the way down into market segmentation and their key vertical industries and the buyer personas, all the way down in the product descriptions and repeatable use cases to bring to market until you do that you can’t even decide whether or not you’re selling people with a Field Sales Team, or you’re hiring a bunch of bdrs and going inside sales, or if you’re going to be a channel distribution model. You know, and that’s, that’s just it on the sales hiring plan, let alone what demand Gen programs or what mix you should have the drive top of funnel traffic, right? So that’s typically where I go is I bring it all the way back down to that from an investor, you know, we look at the same things everybody else looks at, right? We look at market opportunity, we look at team and expertise, we look at products, you know, technology moat, you know IP, and then we look at go to market and whether that’s for looking go to market or Hey, here are lighthouses, here’s our current success today, is this something that we think we can build upon, and then it all gets rooted in the fundamentals of the financial model. And whether or not we believe that the semblance of the organization around at the people can actually take on that market opportunity and can actually make a dent on the world. And, you know, we end a lot of times our decision making process with a simple question. If this company one day sells to Oracle or files in s when it goes public or flips itself to Adobe or Salesforce or any strategic or Heck, maybe even these days, this day and age sells to Thoma Bravo, and Vista or some tea shop. Now, are we gonna, you know, tell her tell our significant others, disappear with our kids and go to a closing dinner in New York or San Francisco or Boston? Do we like these guys enough? Do we like these gals enough for these the types of people we want to celebrate success with and help enable success with and have shared success with, and if the answer ends up being noted that we just won’t even get involved, they won’t take on the consulting quiet, we won’t invest, we won’t advise, we won’t sit on boards. You know, life and career is too short, I think especially in these COVID types of people you really, really, really enjoyed working with,

Peter Mahoney 17:16
you said a lot there, Kyle and I can unpack a couple of things. So the last piece, I think is is really important. And there are a few things in there. Obviously, as you said, you want to pick the people you’re going for a ride with. But more importantly, I think the what’s embedded in there is the idea that to to actually achieve that level of success, it means you have to work pretty hard with people and and collaborate pretty closely with people. And if you don’t want to spend a lot of time or you don’t think the people that you’re collaborating with are the ones who are going to listen with you listen to you or engage appropriately, then it’s less likely that they’re actually going to achieve their potential. That’s

Kyle York 17:59
one clearly it has to be complimentary parts, right. I mean, I, we have a very specific go to market expertise in SAS, we tend to focus the majority 98% plus of our efforts on our York IT company to that. And you know, I think the reality is like, that’s what we’re good at, if they’re already loaded up in those areas, and they deeply need finance help, or they deeply need product development, you know, engineering help, might not be the right fit for us. Right. So I think it’s also for people listening, like it’s knowing your strengths really, really well. And knowing who you compliment and the type of team you fit in well with and, you know, making sure that that’s, that’s as good of a fit as anything else.

Kelsey Krapf 18:45
You mentioned the right people to invest with or, you know, partner with during these covid times, it’s especially crucial. So how has the pandemic you know, impacted your investment approach, if at all?

Kyle York 18:59
Well, um, so I think philosophy wise, you know, we were trying to think a little bit of a counter Silicon Valley approach to fundraising and to capitalization companies, you know, we are dying, we didn’t raise $1 of outside funding till we were 30 million of arr I actually think that’s probably the number one best highlight of the story of dying is we just ignore it and stiff armed VCs until it was truly growth equity and private equity coming in, to help us expand and you know, even part of it was one of our co founders was lead. So you know, it’s just smart have given him a little pat in the back. I’m gonna go on his merry way. So, you know, I think from our perspective, it’s really shined a light in the philosophy of efficient effective cash management and investment management and ensuring that we’re truly aligned with the companies are backing that they’re not Yeah, you guys have seen it the decks startup decks that have like, well, we’re gonna raise this money and then the next milestone literally in the day is a seed round or a series a round or a Series B round, or a series f round. And it’s just like, if that’s what you’re building your company for, then that’s not something I think we want to be involved in, we want to be involved in companies where the cap table is in the hands of the people building shareholder value, which tend to be the founders, the executive teams, the common shareholders. And that’s just incredibly different than venture capital. And if you pick up venture capital, specifically, they raise a big fund or one fund to funds three funds, 10 funds, and they are continually fundraising are paid by limited partners, the people’s money, they’re investing, that’s the client, right? Then they’re deploying capital, they’re raising money again, to deploy more capital. So there’s a perverse incentive to put more capital in every company that they back whether that company should take bear capital, or more capital or not. So I think what it’s done for us COVID is it’s just screened like bright lights, like philosophical alignment, on the sort of effective efficient use of capital proceeds and scale. The other thing, it’s done no more from a deal diligence perspective. I mean, if you’re not able to meet face to face, then you need to do way more diligence on the people you’re backing. And to do that, you have to do a lot of like back channeling and sort of internet stalking and reference checking. And we’ve just, we do so much more of that now than before, we usually get our own pulse of the people by meeting with them, maybe there’d be a call or two, because you’d have a shared like thing connection. I feel like now we’re literally making a dozen phone calls and are asking for references, and we’re talking to other investors. And you know, again, beforehand, if we’re sitting face to face and shaking hands, look at each other in the eyes, we tended to be able to do that on our own. So that’s added a whole new element for us that I think will probably sustain Actually, it’s kind of a little bit more mature than just trusting your instinct and gut and add a little bit more process.

Peter Mahoney 22:06
Yeah, I think there are a lot of processes like that, that you just mentioned that are that are just going to stick. I think if you look at the the idea of remote or hybrid remote kind of working, that clearly is working more, even in our personal lives, I think things like telehealth are going to be more prevalent now. Because they loosened up some of the regulation in the short term because it for safety reasons. And I think a lot of this stuff is going to stick. If you seen Have you seen a big change? If you look at all of your clients and across your portfolio? If you’ve seen any sort of consistent thematic fundamental changes that these companies have gone through, is it really specific to the individual company?

Kyle York 22:51
No, I think you have I mean, I think right when this hit, you know, every single company they should have if they didn’t, but every company on the planet did three key things, right? Number one, they looked at their 90 to 120 day plan. And they basically were like, what, what is our triage, like right now, not knowing what actually is going to happen? I mean, remember, like mid March, we were all just kind of told to go home, right? So it was a little bit like, okay, like, that’s why we don’t know how long this might last, we still don’t know how long this my last. So as a 90 to 120 day sort of triage number to every company. Um, you know, again, every company, if they didn’t, they should just do this now. re forecasted, 2020 and 2021. Like right away. And then I mean that both in the expense side, but also in top line, like, like, let’s like, get super pragmatic, like whatever we told our last round investors, or our last board meeting where our like, perfect world scenario targets, throw them out the window, and let’s be pragmatic and conservative and make sure we have good, better best plans on going through this. And then number three, what I think this is definitely not what enough companies did is, is focus on strategic things that this new world order of like being home, being remote, maybe having more time, as leaders to be alone with your thoughts and reflect and think about strategic projects. I mean, before the call, we were talking about writing a book, you know, like if you if your company wanted to write a book as part of your marketing strategy, then write that damn book, right. And so I think we’ve seen a lot of new bets made that could become the future of business models or new product lines or new revenue drivers. That just again, weren’t possible because you’re afraid to make the bets in a world pre COVID where now it’s like, hey, maybe we should try a few of these things and see if any of them stick. So I would say like climatically, especially in our portfolio. That’s what we pressed and tried to help collaborate and get everybody to do. I think from a macro market perspective, I mean, we work in soccer, like you guys Right. I mean, the enterprise software space, if you look at the public market comps, I mean, the best investment I’ve ever done in my life actually started out as an advisor, earliest advisor for I’m going to market for a company called fastly. It’s a content delivery network that competes with cambridges Akamai earlier today, there are $115 a share, I mean, literally worth 12 $13 billion, I think when I invested, they’re worth 4 million. So you know, these are just, and that’s just on the tailwinds of work from home or remote work. Globalization, like, you know, like people online people looking to distract themselves. And that’s an infrastructure company, right? They performed better than zoom through this. So I think we’ve just seen a lot of like, everyone freaked out, but it’s also like, hey, there’s going to be macro crises, they’re just going to be micro crises. Not everybody’s going to face hardcore headwinds, some, some companies are actually gonna get immense tail winds, ride them. And so I do think there was an inclination or instinct for everybody to like, say, the sky is falling. And actually, in your industry, you might be crushing it. So you know, let’s, let’s look at how you maybe, maybe turn the negatives into a positive?

Peter Mahoney 26:11
Yeah, I think that’s really smart, Kyle, and certainly there are companies who, who’ve done really well and in will continue to do well, fastly is a good example. And in zoom, and Akamai and others have done well, because the The reality is that there’s this short term turbo boost, in remote working, but people are figuring out that you can remote work, and it’s going to be more accepted. And it’s accelerating digital transformation. In general, we’ve seen a huge bump in demand for our, you know, marketing planning and budgeting platform, because the reality is people need an agile plan, now they know that things are gonna change. And so we we’ve seen pretty significant growth from that. But then you look at companies, you know, there’s some really great companies from brilliant people like Paul English, who started Lola travel, and you know, what, nobody’s traveling right now in in their thinking and working on I was just talking about the about this, they’re, they’re working on some really creative things around some, some augmentations of the business model that that that they can do to to create some some growth opportunities. So they’re thinking strategically, and I think you’re right, the people who find that opportunity to to think strategically about where things are going, are the ones who are going to long term long term make it.

Kyle York 27:37
Yeah, and I think in the early stage, guys, I mean, Peter, like, the early stage, like COVID, does shine a light on some business fundamental stuff in our portfolio that was like, hey, maybe they’re actually just spending too much in marketing. Or Heck, maybe they’re, we’re overly balanced to engineering and product development and very light and sales, right? Like, you know, or, hey, they have way too many third party consultants, like, this is a good opportunity to clean it up. So I feel like so much of it was like, COVID never let a good crisis, you know, you know, whatever, I guess I can say excuse. It’s like, sometimes I sit there and be like, Oh, yeah, you were just, we didn’t notice it, because we were building a company. But you’re spending way too much money on third party analyst firms, you know, for a company of 1 million arr. Right. So I think that was like definitely one thing another example like Lola and I’m into know that just being friends with Mike but there’s one called Mayflower venues. And in Boston, you know, it’s a, it’s a wedding venue management platform for like people who own barns and apple orchards and pumpkin patches, tin Lake houses who want to turn their home like an Airbnb, when you turn your home into a into a hotel, they wanted to turn into venues, and you know, this hits you, there’s no more weddings, right. But there will be a trend coming of outdoor weddings in the future. And they started to shift more like the value being it’s like a marketplace, the value being to the bride and groom, turn the value into a venue management platform for the venue. And then now they have time because they’re not hosting weddings to evaluate technology and how that might make them more efficient, more automated, more modern, and put those tools in the hands of the business model became more of like what I like, which is subscription, and in a way from, you know, the kind of consumer marketplace, and eventually they’ll marry back together. But it was a it was a quick shift in strategy that I actually think is gonna have more staying power and predict potentially long term create more enterprise value. And I think I think that’s exactly what this is enabling also for Mike and Paul and Rola.

Peter Mahoney 29:43
Hey, that that makes a ton of sense. I want to pivot a little bit to is you know, our audience is made up of a bunch of Marketing Leaders or aspiring Marketing Leaders and and I often when I’m working with marketing people earlier in their career, tell them that an early stage companies actually great opportunity because you you can wear a lot of hats you talked about in the first company that you were you were at, you had an opportunity to do a little bit of everything. And I think it’s a great sort of internship model that that is, is really useful. But if you look at so from your perspective, when you put your investor hat on, as an example, one of the most important roles from the investor side is recruiter, you’re you’re the person who brings in talent to your portfolio, it’s one of the key value propositions that you can deliver often in. So when you’re looking at that, I want to bring market and leader into one of my companies now and tell us a little bit about what you’re looking for. Because again, our audience, especially people who haven’t reached the peak, yet, they’d love to know what that person who’s trying to find that next great person, what are they looking for in the next great marketing person to put in one of their prize portfolio companies?

Kyle York 31:02
Yeah, that’s great question, in my perspective, so unique because, you know, when I was originally hired at Dine Out of my first startup, I was a VP of sales and marketing. And I quickly titled jump to Chief revenue officer, but I kept marketing and BD and Corp Dev and product marketing and demand Gen, and sales and Success and Support ours, you know, I had all functions, right. So, you know, I only actually carried this cmo title for like, a hot minute in like, you know, 2015, when we were hiring a new head of s, SVP of global sales, and they were transitioning me to like a chief strategy officer, like sacred cow role, like don’t leave, you know, type a role. Um, but it’s funny, because I always kind of ran marketing. And my what I always talk about when it comes to marketing leadership is ultimate accountability, and the need to connect to outcomes and results and revenue, and customers. And I think, oftentimes, some traditional tracks of marketing, maybe more on the creative or the brand, or the campaign side, sometimes fear or the SEO or sem, sometimes veer too far away from that, or understanding your place in that funnel. And in the sort of KPIs that drive towards that ultimate accountability, that sometimes like those are not the people that ended up being chosen for those top tier marketing roles, especially in technology. I’m talking mostly about just given my background. So I think, you know, if you’re out there today, and you’re trying to figure out how to do that, I think it’s really getting close with understanding sales and working your way back up the funnel. And, you know, right now, roles in user experience, user experience, design, UX, conversion, these are areas that are like practically impossible to find, in growing companies, as well as married with demand generation functions. I mean, truly being able to drive top of funnel demand that converts to qualified sales opportunities, you know, is critical these days, because, you know, one time we had this CFO consultant, Rick DeRose is from he used to work for Gomez, their web monitoring company, and then cuc is bought by Compuware. One time, he asked me a simple question early in my career when I was in those roles and dying, he said, Are you feet constrained? Are you weak, strange. And I literally asked myself that every day now as a CEO, I asked myself that as a GM inside Oracle, I asked myself that as a CRM as a CMO on my lead constraint, and my feet constraint on lead, obviously, being on top of funnel marketing, feet being reps, PDR, South bounders, you know, people hammering pavement for you? And I think that’s a tough, that’s a tough question for people to answer. So I guess my point is, make sure you are attaching yourself to some of these core skills that are hard to find the UX kind of customer experience side and the demand Gen lead gen side, but also, you know, touching yourself as you can to the sales organizations, those KPIs, those policies and those people, because at the end of the day, if you can show you can drive revenue, you will be one of the most important parts of the C suite and any company.

Peter Mahoney 34:25
Yeah, especially early stage companies, obviously, I think in any company, I think the idea of accountability that you brought up is really important the ability to demonstrate value in in optimizing deliver value. And I’ll point you to, I know, my, by the way, I’m not going to throw shade on Kyle for not reading my book yet because I know just hit his desk just yesterday or something so he hasn’t got through it. But there is a chart in my book that I’ll point out that’s that talks about what’s called the integrated marketing machine. In in, it’s sort of a more A blown out version of viewer Leads Leads your feet kind of question. And because that that’s exactly what you need to understand the unigestion marketing is an interconnected system. And as you highlighted, there’s a top of the funnel, there’s a bottom of the funnel, there are also lots of steps along the way in there things that influence the funnel, and you need to understand how all of those points in the system are interacting. And in where the choke point is, and where there’s a lever for growth. We just went through this and you know, we’ve recently expanded our, our BDR team. And we found that in the first quarter of their existence, they contributed more revenue and more cash than we paid for them. So the question we ask is, well, we have two what happens if we have 10 in in start thinking about those scalability so I think people with that mentality, and and in thinking, the people who think about not only overall sales in driving the top line, but think holistically about business value, I think are really important. And that was embedded in some of your comments that you made.

Kyle York 36:14
I mean, it says business value, and it’s the repeatability of the business value, like Like, a lot of execution is like mechanical and boring and mundane. But like when you do it consistently over time, that’s what builds brands. I think, like, I think I weirdly come at this from a totally like, I don’t think I’m a very good typecast of a CMO or CIO or pick a title right? I, the way I built companies as an operator is brand and sales. Right like evangelize the story, have a story stand for something, make sure it’s disruptive and not lame and not copycat, like actually have points of views and put them out in the world every day all day for the loudest rooftops and create as many champions and advocates around that story, you can then close goddamn deals, right? Like, literally like those are the two ends. So we’re talking like even above the top of the funnel, I’m talking in the clouds above the funnel, and then like the dollar symbol at the end, right. And, you know, I hired typically around me to fill in all the mechanics of your chart, because I know about myself that I’m going to be just absolutely atrocious, the mq l to Sal handoff, I just think that stuff is like so boring, and so mundane and so annoying and fogged over. Right. But there are people who are really, really good at understanding that handoff and making sure that it works on both on both the marketing and the sales side. So yeah, I think I think of it. I think of sometimes I myself like even though I’m a node operator, sometimes I think of myself operating kind of on on those ends of the spectrum as well.

Kelsey Krapf 37:53
For early stage companies, do you prefer to bring up and coming for some Marketing Leaders? Or do you want someone with a proven track record?

Kyle York 38:05
I fanatically talk a lot about builders versus managers. Hmm. I think it depends upon the sophistication of your of your go to market emotion. I also think it’s complimentary parts we discussed earlier on your other leadership. Ah, I’d always been on the rising star though. The majority of my career when I’ve hired people who had been there, done that early stage. I actually like literally just tweeted this, I wish I wish I could like I wrote hire wisely. And it was something like stage expertise level expertise, VC versus bootstrap expertise, manager versus individual contributor expertise, manager versus process expertise, or sorry, builder versus process expertise. Like, there’s so many things you have to look at, based on the stage of the company, the other executive, team members that go to market motion. And it’s honestly really, really, really hard. But I’ve had the most success in my career, when I’ve hired the rising stars and given them that next level up opportunity to go out there and earn it.

Peter Mahoney 39:09
It makes a lot of sense, especially coming from, as you described earlier, you were that rising star earlier in your career. So I think you get it right? You, you

Kyle York 39:18
you can kind of sniff it out. You like alright, that person has it or they don’t. Now that’s not to say by the way that you know, we had a really wonderful CFO that was hired in who was whose big company guy who was able to come into the culture, I can invest in and fit in really well and do amazing things for us. So we when I say like experience versus you know, rising star, I don’t mean rising stars have no experience, right? It’s just, you know, this person had to be a CMO twice before, like companies going from 3 million to 50 million. Like, like, let’s be sure you’re not looking for the thing that like kind of doesn’t always exist. Let’s let’s look for the thing that we can create more more of the future CMM

Peter Mahoney 40:01
You mean you don’t look for people who’ve had 25 years of SAS experience in the Bitcoin? And in

Kyle York 40:08
cryptocurrency landscape? Yeah, and took companies to unicorn status three times over. Like, I feel like a lot of times I do, by the way, sit in board calls. Yeah, we’re an investor, but we really position ourselves as the extension of the operating teams we back and as entrepreneurs, and the amount of times I try not to, like represent preferred shareholders, I try to represent the company and the people we’re working with. And a lot of times I sit in these meetings, and I’m like, you’ll get the like, you know, the PE firm who’s like, you know, I just don’t understand why you guys don’t have $300,000 a year clients. And I don’t understand why someone from PTC doesn’t just come in here and want to run your marketing efforts. And you’ll just sit there and you’ll say, well, because the products not worth 300 grand, your average selling price is 25. Just do more of that HubSpot got a pretty big company on $8,000 a year customers dying was $18,000 a year customers like if that’s what you’re good at, and that’s an inside sales motion with BDR is an e commerce. That’s not a field sales organization where you have half a million dollar reps. But I think what you end up seeing a lot is too much pattern mapping to, you know, hopeful outcomes, not, you know, bottoms up planning and what will actually will actually get you there from a lot of those folks.

Peter Mahoney 41:24
Yep, that makes sense. So a couple last quick questions. And I think we have to, we have to wrap we’ve gotten a lot of places here in this discussion, as it didn’t surprise me just having spent some time with you before Kyle, I knew we were going to do this. But one thing just for for our listeners, you know, give give them a quick tip on how they can connect with with your company with York IE, in and why they might want to want to do such a thing. Certainly they should follow you on Twitter, because I find you highly entertaining there. But But how else should they connect with York? Ie?

Kyle York 42:03
Yeah, sure. So yeah, I’m trying to run k York 20. And then which is my football number. Good luck number after barry sanders best running back of all time. And then we’re you’re at your growth across all social channels, and our website is your God, ie, that’s actually stands for investment enterprise. It’s also the biggest deal dye number one was in Ireland, which is the Irish TLD. So that’s why we actually have that top level domain name. So you can find us in all those places, you know, we’re putting out lots of education on how to build and scale a startup. We have consulting and advisory advisory services, for business growth, for market product strategy and for marketing communication services. And we also are an early stage seed investors. So we will invest in the cream of the crop that we engage with. We’re also very excited where we’ve teased it out a little bit. We’re launching a platform for market data and analytics. It’s really a competitive intelligence platform. I think of it almost like management consultancy meets analyst firm, that, you know, we plan to launch next spring that I think will be very valuable to entrepreneurs trying to trying to find their find their path. So lots of ways to connect with us and look forward to doing it.

Peter Mahoney 43:13
That’s great. I think we’ve got one more our favorite question. And then so Kelsey, why don’t you take us home?

Kelsey Krapf 43:19
It’s no surprise, you know, this podcast is for marketing leaders for those that are listening. So what advice would you give, you know, those rising stars of those current CMOS?

Kyle York 43:29
Yeah, I think what I give you that advice is to be very well rounded. Um, I think it’s important that you obviously play to your strengths and not try to be something that you’re not. So double down there, but also be well rounded and attach yourself as best you can. Robin.

Kelsey Krapf 43:44
Awesome. Well, thank you so much for your time today, Kyle, want a wealth of knowledge that we’ve learned just from listening to you and doing this podcast, make sure to follow the next cmo and Plannuh on Twitter and LinkedIn, and you can look at your guy in our show notes below. And if you have any ideas for topics or guests, you can email them to Have a great day, everyone.

Peter Mahoney 44:09
Thanks Kyle.

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