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Kyle York CEO of York ie

September 30, 2020
To listen to the full episode, click here

Speaker 1: (00:00)
Welcome to the DNA and experience podcast from cloud app, where we discuss how and why creating an experience is so important and the psychology behind what makes an experience. So great. Thanks for joining us, everyone. I am excited to have Kyle York with me. Kyle is the founder and CEO of York. I E also a long time, a user investor and board member for cloud app. So I’m excited to talk a little bit about, uh, the companies he’s built. Also, we’ll talk a little bit about cloud app today and some of the things we’ve been doing over here, uh, Kyle, you want to give a kind of quick background on yourself and kind of where, where you got to, or how you got to where you are now.

Speaker 2: (00:48)
Yeah, sure. Great. Thanks for having me, Joe. It’s exciting to be here. Uh, you know, I’m a huge fan of yours and cloud app, so awesome. Um, yeah, so Kyle York, uh, cofounder CEO and managing partner of York III, we’re a strategic advisory investment and operational growth from, uh, we’ll get into more what that means. Uh, we’ve got a sort of hybrid business. That’s building a SAS platform, it’s advising and consulting with startups on growth and also investing in early stage rounds, uh, predominantly focused on B2B software companies. Uh, I, uh, have had a long career in SAS. Uh, I guess I can say long, but you know, the reality is, um, I’ve only worked in the recurring revenue, SAS business model. So that sort of dates me. Uh, I started an education technology, SAS company for private schools, uh, called the Whipple Hill that was eventually sold to black, bought a public company in Charleston, South Carolina.

Speaker 2: (01:40)
That’s where I got my start, you know, uh, cut my teeth in marketing sales business development roles spent a bunch of time in California for that company. And then moved back home. I’m actually talking to you today from Bedford New Hampshire, my home. Uh, and I moved back here for a company called dine, which was a, at the time a consumer kind of infrastructure company that enabled people, uh, in the early two thousands to basically name their home network. So they could remote access back into their, uh, you know, uh, their music or their files, you know, inside their home network. Um, it turned out that domain name system we specialized in. I was really good at doing maiming performance, routing security around, uh, cloud end points and modern websites that were globally distributed. Um, and we ended up building a very successful company and dine.

Speaker 2: (02:29)
I was chief revenue officer, uh, had marketing sales services all under me, uh, ended up becoming the GM of that company when we sold the Oracle in 2016, uh, for a rumored, uh, rumor $600 million. Um, and, uh, you know, along the way, just actively angel invested, advised, um, you know, a business guy, a sales and marketing guy. Um, obviously technology companies tend to be founded by technologists and engineers and have made a career out of helping translate them into value for their customers. And, um, just love, love working on the earliest stages. Oracle wasn’t really, for me a little too little, too little too big, um, and several excited to be building what I’m building in New York IAE, which I’m sure we’ll talk a little bit more about today.

Speaker 1: (03:12)
Definitely. Yeah, that’s really great. I think you mentioned no, a key piece of your career has been focused on recurring revenue and obviously like a big piece of that is having loyal customers and, and having people that want to keep paying you. What’s, what’s kind of the DNA of a good customer experience. And how have you kind of tried to focus on that and provide that so that companies want to keep, you know, being part of your full

Speaker 2: (03:41)
Yeah, absolutely. Um, I think it all starts with the strategic customer and I always work with startups, especially in the earliest stages about the funding, what that is and what I mean by strategic. I think of it kind of like a triangle, um, a brand, you know, you know, that everybody knows that you can Mark it around. Um, so in your case, you know, it’s the XenDesktop, it’s the, Adobe’s, it’s the, it’s the customers that we know in love. It could be even in startup land. Um, it’s also a company that is paying you something and paying you something consistently, uh, something that is landing and expanding and not just retaining, but also growing. And then number three, they find strategic value in the capability that you offer. These ended up being your lighthouse, customers, your referenceable customers, uh, the customers that not only you put a logo on a webpage, but will actually take a call from a prospect and, you know, sit on your customer advisory board, you know, do webinars, which you do frequently, uh, collaborate with you on cross marketing functional stuff.

Speaker 2: (04:42)
So I think when it comes to that, I think a lot of startups struggle with that trifecta, right? And getting customers that fit into those three things. It’s many times you’ll see a company that’s a big logo and might find a company to be strategic value, but they pay you $50 a month, right. Or, Hey, they might pay you 10 grand a month, but no one’s ever heard of them and they don’t even find the product or capability valuable. So I think once you nail that trifecta and you, and you build your sort of go to market to make that repeated ball across market segments and industry verticals, um, at that point in time, I think is when you can really start to focus on, um, that customer experience and happen, uh, in the customer experience, as they analyze the documentation, support, customer service, customer success, those types of things, and it, but until you nail that trifecta and you can make that repeatable, it’s almost premature to even overly obsess over that. So, and that’s a, that’s a rise of a startup, uh, type of challenge, and when to sequence that out and, and, and nail that. But I think it really comes down to all those things and the moment that those companies can be referenceable, um, you’ve got obviously, uh, not take advantage or overuse each individual customers and they actually do it. Um, I think that’s when, you know, you’ve nailed the customer experience and the relationship experience with those guests.

Speaker 1: (06:07)
Yeah, definitely. It’s, it’s getting your house in order, like you said, having that strong foundation and, and, uh, being able to kind of really connect uh one-to-one uh, initially, and then being able to scale that and find ways to really make it more efficient and design those experiences.

Speaker 2: (06:26)
Yeah. And I think don’t underestimate the relationship building. I think so much these days, especially in software, um, is sort of hands off and you hear a lot about like product led growth and all those things. They’re all wonderful, but I think your company and its life cycle will ebb and flow when you’re the technology leader, when you’re the relationship leader, when you’re the brand leader, when you’re the customer experience leader, um, these things kind of are a little whackamole meaning they don’t always expose themselves all at the same time. Obviously the best companies have all functional areas of the business at the same time, but in my run at die. And I mean, there was times where we were hands down the technology leader times when we had the best API APIs and the best user experience in UIs. Um, there was times, you know, the only thing we really could control was the relationship cultivation, the support, the customer experience. Because again, if you have a good relationship, if the product has issues or bugs, or you launch a new gooey and it’s, you’re getting customer complaints, you can work through it. Um, so I think you really need the root that in building your organization to make, um, relationships first and foremost, and be able to expose executives. Um, it can’t, you know, you can’t just push relationships down in the New York. It needs to be up, down, down, up across the board.

Speaker 1: (07:45)
Yeah. And so, you know, we’re, we’re kind of in like a relationship, obviously key, but we’re in this like business travel is obviously way down people aren’t connecting their way, the way they used to currently, how can video and visuals, obviously talking maybe a little bit about cloud app here, enhance your connection with the customer when maybe you can’t fly out and have dinner with them.

Speaker 2: (08:11)
Yeah. I mean, well, first of all, even pre COVID, um, you weren’t flying out and meeting every customer face to face anyway. So I think you certainly were in the, in, in that trifecta, I just mentioned, or maybe you had, you know, a hundred thousand dollars client or maybe all, it’s a no brainer. I need to go sell Netflix, uh, as a customer. Um, you know, I, so I think, I think you have a different sort of tiered relationship structure that we’ve always had as it relates to. How do you build those relationships? I think now more than ever, um, something that, you know, I’ve seen talked about it a little bit right now, but not as much as you think the personal brand and the personal accessibility uh relate-ability um, no kind of conduction you make, um, is more important than ever for companies because people are so clearly representing, uh, the companies.

Speaker 2: (08:59)
Um, that’s always what it was face to face, but if you think of big conferences where there’s 40 by 40 booths or 10 by 10 booths, it’s like, you’re actually engaging with the company. There happened to be representatives of the company at those live events. I think now what you’re seeing is the, the individual power of, of, uh, of an account director of a head of solution architecture of a marketer of a customer success person, actually more and more power is being put in their hands because of the tools like cloud app that enable that direct connection. Um, and it’s all about access, transparency, genuineness, authenticity, um, your people are becoming even more important, um, stewards and, um, cruise missiles for your brand building, right. And your customer engagement. So I can tell you from my perspective, it’s, it’s just shining an incredible light on personal brand, on the need to, uh, be who you are at home, who you are at work, uh, have those things inter intersect and have, have it be all the same.

Speaker 2: (10:00)
I mean, a kid could run in here at any minute and I need to be the exact same person with my family that I am in my work setting and my work environments are on, on a, on a podcast interview. Right. So I think it’s never, it’s never shined a bigger light on that. And it’s why you’re seeing such a boom in, you know, uh, enterprise software. I mean, the public markets are up nearly 25%. Um, since the beginning of COVID this calendar year, um, you know, private companies, you know, I’m seeing just investments continue to shine. Um, and companies like cloud app or just poise because from day zero, they were built, um, to help people communicate and collaborate and connect. And, you know, that’s really, that’s really what is required and what brands really need to, um, I don’t know, open up on especially large enterprise brands. I spent a long time in Oracle. They gotta get comfortable with lots of foot soldiers, uh, out there in the wild, and they’re not going to control it the same way. So they better have the rates through my process, guardrails, brand guidelines, engagement, guidelines, and tools to make them all, make them all sing.

Speaker 1: (11:06)
Yeah. There’s just like that layer of authenticity that you mentioned, like, uh, one of the programs as helping build that Adobe was, was, uh, building up those executives as thought leaders and people that were had a public face. And there was industry interesting stat. I always say, like, we would do this brand push and we put $500 behind the EVP of sales, like a tweet or Facebook post or LinkedIn or whatever. And we’d get 10 X the engagements that we would for like $5,000 behind a brand post. So it’s like less money, more efficient. People want to connect with a human. Um, it, it, and, and right now, like, especially you said kids running in, like it’s authentic, you know, we’re having board meetings and kids are running in and dogs are barking. And, uh, you know, it’s just, it’s just the way it is. And we’re all kind of on the same plane and it’s really kind of, kind of in kind of fun and, and interesting to see those worlds collide.

Speaker 2: (12:08)
Yeah. I feel like in like startups and entrepreneurship, those worlds collide more just because it’s like this always on sort of gritty, you know, the, the work life balance is a weird one. So, I mean, I’ve always felt that in my startup career, I think in, in, in larger companies, um, that humanization of like corporate America or, you know, it, or the global 2000 is, is actually where I’m finding it the most fascinating. I mean, I’ve also, you know, to your point on executive programs and things like that. I mean, I’ve always complimented and worked with technical founders. My bosses have always been engineers and entire career. Every single boss I’ve ever had has been an engineer, um, and by nature, an introvert and, uh, personality wise kind of intrinsic. Um, and so, you know, being that translator as a marketer and having tools like cloud available to you to help you do that, um, is critical.

Speaker 2: (13:05)
I mean, we, we would do things like, you know, um, at Oracle, for example, we’ve recorded internal meetings, um, because that was the only time some of our technical leaders would speak out loud in front of, and then we’d synthesize out, um, the key components of their talk and turn them into public facing content, both micro and, and long form. And so, you know, all of a sudden, you know, they’re a celebrity on the internet and they’re helping us drive our brand forward and helping us relate to our customer base and grow our revenue. Um, and they don’t even necessarily know, no, it, um, that’s the thing I think about personal branding is not, everybody’s going to be good at it, but companies need to put together programs, leverage tools and capabilities and help, uh, the people who aren’t get good at it by, by managing, managing it systematically. Um, and the best brands in the world, um, have always done this incredibly well.

Speaker 1: (14:02)
Yeah. I agree. I think you, you catch lightning in a bottle definitely. When you find that tech leader, that’s, that’s willing to kind of be on stage. Um, I want to talk a little bit about your ke, um, kind of, I obviously saw you kind of launch it and, uh, you know, the success you’ve been able to have early on with it. What, what do you guys, what’s kind of like, your, your customers are kind of like the people you invest in. So how are you kind of differentiating yourself from all the other kind of growth launching a startup advisors out there, uh, that provides, provides a different experience?

Speaker 2: (14:44)
Yeah, so I mean, our vision is to reshape the way startups are built scaled and monetized. Um, the Silicon Valley culture of fundraise, fundraise, fundraise, uh, diminish founder equity and dilution. Um, you know, the cap table imbalance, um, the sort of growth at all costs mantra is very different than how I was raised. I was raised in a small family business. You know, we, if we didn’t make a profit, we didn’t eat dinner. Right. I mean, it was that basic. Um, and you know, as you, as you grow, I mean, dine actually bootstrapped itself, the 30 millionaire, or without raising a single dollar of outside capital, we happened to do it in Manchester, New Hampshire or headquarters, whenever when told us we couldn’t. Um, you have a lot of this experience being in Silicon slopes in Utah, and, you know, in a burgeoning scene that’s been created over the last two decades.

Speaker 2: (15:34)
Um, very similar here in Southern New Hampshire, North of Boston. I mean, I’m 45 minutes from Boston, but people think we couch tip all day, right? So, so you take that sort of, uh, product Yackey pragmatism and you take that sort of family business roots, and you bring that to a startup culture. That’s very, very different. Um, but by default you have some differentiation there. Um, also because we work in deep technology and up to stack and to Apple SAS applications like cloud app, um, you know, we have just a lot of domain expertise in layers of the technical infrastructure that people don’t understand from storage to compute, to dev ops, to dev tools, uh, cyber, uh, to DNS, right? I mean, we have a different level of technical competency, um, that I think a lot of startups do, which demands a lot of credit commands, a lot of credibility from technical entrepreneurs who are looking for help, right?

Speaker 2: (16:23)
It’s not that we’re just really good functional marketers are really good functional sales and BD or finance team. We really bring that to bear. Um, I think our model is just incredibly unique. I mean, we’re trying to go after everybody from investment banks to management, consultancies, to PR they are firms, uh, to VC, um, you know, to, to really the gamut of, of players, including even analysts firms that support startups. I don’t think a lot of these have really down scoped appropriately for the speed pace, urgency, uh, accountability on low budgets, um, flexible budgets, flexible engagement models that startups command. I mean, I can remember paying 10 grand a month for a CFO consultant and eight grand a month for a sales consultant and 20 Gantt grand that aggregate a month for analysts firms. Like this is, this is like not okay, unless you’ve raised $10 million in your Silicon Valley, you know, series a darling.

Speaker 2: (17:21)
Right. So how do you help create a different model of engagement? The only way we could do this is based on the track we’re going to have as an angel and as an advisor. I mean, I joined with cloud app while I was still working right. 1% of my time. So we’ve taken a lot of what we’ve done historically, uh, helping these companies kind of be a shot in the arm from a growth brand, a scale perspective. Um, and the only way to make it scalable is for me to build a large team that I’ve self-funded as well as, um, build technology, a technology layer to help automate a lot of the mundane and, um, basic workflows. So we have a market data and analytics platform currently an internal beta, um, that we plan on launching in the spring of next year, that really helps companies, um, you know, discover a track report on, um, companies, markets, uh, go to market activities.

Speaker 2: (18:10)
Uh, I think it’s gonna really kinda come at, come at the world from market competitive intelligence perspective very differently, um, and also enable us to create more engagement models because there’ll be like a self service way to work with York IIE that isn’t so heavy handed. We also, don’t only work with investments. We have about 25 active engagements right now, uh, about 15 of them are, uh, investments as well. Um, so we layer on the advisory consulting and we call them modules because we’ve kind of productized it. Um, and then on top of that, we’ll, we will work with companies that are later stage or too early or not in our director. We have a couple consumer and marketplace brands who predominantly invest in B2B SAS, but we can still help. Right. So we try to find different kind of engagement models and be super flexible.

Speaker 2: (18:59)
And that’s possible because we don’t have outside VCs for Yorkies management company. Um, we also don’t have a traditional find. We operate a evergreen syndicate model. Um, so we have high net worth individuals, family offices, who give us a five-year annual pledge, and we’re able to go to that in our investment model. So again, without collecting management fees from them, it gives us even more flexibility. So there’s lots of different angles we take on it. Um, I think at core though, you know, we’re not, um, retired operators, we’re active operators, we’re building our own SAS platform. We’re an extension of the operating teams that we are working on. I just passed a million ARR last week, um, you know, on nine months of, you know, our go to market and, you know, my goal is to grow, build a great company. Don’t let me kept cloud app, you know, um, and built a great, great company. And I think, um, the companies you back, whether through investing advisory or consulting or product eventually appreciate the fact that we’re coming from the active school of hard knocks, not just the career legacies we created on top of our past experience.

Speaker 1: (20:04)
Definitely. Yeah. I mean, I think you pointed out a lot of really cool things that that is doing. Uh, what, what is kind of like, take me in the evaluation process, like when you decide to invest in someone, how do you kind of figure out what’s step one, what’s playbook, one for, uh, probably different for each company, but how you kind of assess, uh, what to do first with, uh, with a startup you’ve invested in?

Speaker 2: (20:29)
Yeah, well, I mean, frankly, this is really, really difficult because of our inbound deal flow. Um, the one thing we do not have a problem with is deal flow. Um, we see somewhere in the neighborhood of 40 to 50 inbound software companies per month that come to our website or come to us on LinkedIn, come to our social channels or read our newsletter and engage with us about a funding round or potential funding round. So, so imagine that. So we had to really get really rigid about creating a team and a process and a structure to evaluate the tippity top of the funnel, to decide who we’re even going to take to the next step. So my team doesn’t really even bring me in until it’s a company that they can see us investing in and they want me to learn more. So it’s kind of like no different than, um, a sales pipeline of when do you bring in your executive sponsor to help close a deal or to evaluate a deal or a negotiated deal?

Speaker 2: (21:23)
Um, that’s kind of the way we run York IIE. We take everything less as we aren’t investors by Draymond and grew up in, you know, the ibanker, you know, kind of investment VC community. We grew up as operators. Everything we do is operationalize like a, like a company, right? Um, when it relates to that, getting through the noise, I think number one is we call it our market and approach to company evaluation. Every single company we look at it’s typically founded by a product or engineering person. Um, who’s sitting in the seat, founding CEO, technical COC, um, all of these people think of product I would approach. It’s why they built the company they built, right. They saw a problem in the market, a gap technically, and they knew they could create it. What we look at is, okay, how’s that interplay in the market?

Speaker 2: (22:07)
How large is the market? How disruptable is the market? Are there established players, are there new players? Does this company have a go to market bottoms up plan to attack the big vision, but in a systematic pragmatize programmatic programmatic way. And that’s really how we have we cut through the noise. Um, and then the rest is like every other investment company. We look at, um, market opportunity. We look at product technology, IP, moat, uh, we look at traction and go to market plans. Uh, we look at the team and we look at financial financials, right. Um, but you know, lately we’ve, we’ve had to almost make it even more simple. Um, you know, if this company sold in five years for a hundred million dollars, um, would we go to the closing dinner, it’d be thrilled for their success? Do we like these people? These are the people we want to collaborate with.

Speaker 2: (22:57)
Right. Um, is this a company that I could see myself being the CEO at? And they got more, I’m not, I’m the CEO of my own ever bring company. I’m going to do what I’m doing for the next 20 years, but do we think we can be helpful that we fit in? Joe went out on my partners are very different. You’ve met, have very different skill sets and background Adam’s come more of a skill set like you, uh, Joe is more corporate development, finance, FP, and a, um, do we actually compliment these teams? Can we play a role to help them get to the next level? Because we want to feel reward out of the work we do. We don’t just want to see a company grow and they never call us and we make money. That’s great, but that’s not what we’re what we’re playing for. So I think some of those angles are really how we think about, you know, cutting through the noise and getting to the 10 to 10 to 15 deals, investment deals per year. Um, we’re going to work with, and the ones we don’t, again, we want to have much a bunch of mechanisms through our SAS platforms, through our consulting modules, um, through our network that we can still work with a ton of companies. Um, even if it’s just about creating content and curriculum about growth and, you know, getting people to buy into that.

Speaker 1: (24:01)
Definitely. But I, you know, I think you touched on a few of these things along the way, and it’s been a great conversation, uh, really enjoyed kind of learning some things from you and, uh, our audience as well. Um, I, I like to kind of have you look in your crystal ball at the end and, uh, you know, you’ve touched on a few of these things, but what do you think the future of experienced businesses? Where, where do you see, uh, you know, asynchronous video obviously is a piece of that real time, video relationships, uh, designing experiences, where do you see things kind of rolling out?

Speaker 2: (24:39)
Yeah. I mean, I think at the end of the day, um, the world is flattening big time and, you know, even before COVID, I mean, people are living and working where they want to live and work. I mean, I think I’m proof of that. I mean, I love my life, you know, in new England and, you know, I’m glad I live here and can raise my family here. Um, there’s people in my career told me I’d never be successful in technology if I wasn’t in Silicon Valley. I mean, you know, so I think you’re seeing a flattening of the world. You’ve seen Steve Case’s rise of the rest. You’ve seen what Brad Feld and guys have done down in, in Boulder. You know, you’re seeing, they call them ecosystems in second and third tier cities all over the place. But I think what you’re actually going to start to see is more communities built in other places of people who work for the Adobes, the Oracles, the cloud apps that you work, I use that are just distributed everywhere, which means that the technology we’re using today, um, is going to need to be innovated upon.

Speaker 2: (25:39)
And new norms are going to be created around how we work and how we live and how we engage. Um, you know, and that’s just gonna require more and more technology and capability, um, and more and more automation, right? I mean, it’s, it’s, it’s hard to fast track getting to know somebody when you’re not actually seeing them, um, even in our investment decisions. We’re making, going back to the last question a little bit, Joe, I have to do way more, way more. Backchanneling black ops sketchy stocking, where when we decide to invest in someone I’ve never met in person, and I can’t look eye to eye and shake their hand, right? So, so, you know, the world of like research and data and tracking individuals and companies and markets, I mean a lot of what we’re building in New York, I use fuel platform that we’ll bring to market, or eventually it’s less about the human to human and more about market spaces and trends and companies, but it’s just, it’s just automating that and making it faster and quicker and making us all more prepared and more, um, context, low lead, um, than we’ve ever been before.

Speaker 2: (26:48)
Um, so that when we get on calls like this, we actually know about the people we’re talking to, where they live, what the weather’s like, you know, what the sports scores were last night, what the local news is, you know, is there, you know, a community on rests happening right now in your neighborhood? You know, um, I think we just need to be a lot more aware. And so I think it’s going to be the manifestation of that, you know, being more prepared and making sure people are filled with context, as well as the collaboration tools coming together, um, and innovating, that’s really going to be the next, the next gen. I think of experiences amongst, amongst each other, in our careers and lives.

Speaker 1: (27:27)
Great stuff. Really appreciate your insights on experienced business York, IIE,

Speaker 2: (27:33)
Lots of different stuff going on and appreciate your background and kind of taking some time out this morning. Thanks, Jerry. Appreciate it. Keep up the good work. Especially with that hairdo. It’s really, really coming together, grow it, grow it out until there’s a vaccine. That’s right. I love it. All right. Thanks God. Thank you.

Speaker 1: (27:54)
Thanks for joining the DNA of an experience podcast. We hope you learn something that will help improve your collaboration and enhance the experience you create for your customer. Join the collaboration 2.0 movement today by getting cloud app. The instant business communication tool used to create instantly shareable videos, screenshots, and gifts. Perfect for both internal and external communication. Get started for Thank you. We look forward to seeing you next time.