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Kyle York is the Chief Strategy Officer at Dyn where he has been a long-time executive, having helped scale the company from 30 employees to nearly 500 in his 8-year tenure. He has held go-to-market leadership roles in worldwide sales, marketing, and services and his current focus is on corporate strategy with a focus on positioning and evangelism, new markets, strategic alliances and partnerships, M&A, and business development.

As an expert in global Internet and technology trends, Kyle has been featured in USA Today, Wall Street Journal, Washington Post, TechCrunch, Entrepreneur and is a frequent speaker at technology conferences around the world. 

Kyle is also an active tech investor, board member and startup advisor. Some of his investments include  CloudApp, Datanyze, Fastly and YORK Athletics MFG.

You can follow him on Twitter: @kyork20

He will be live on September 8 starting at 930 AM PT for one and a half hours during which he will answer as many questions as possible.

 

  • AA

    Aldin A

    over 3 years ago #

    Hey Kyle,

    Thanks for doing this AMA!

    1)What are things startups should do/focus on to increase their survival rates?

    2)What are the subtle (and not so obvious) things you see early stage companies screwing up on that they really can't afford to screw up, and how do they fix them?

    3)What are the most important lessons you've learned in your career?

    4)Can you talk about the challenges you've faced when scaling the business and how dyn has over come them?

    Thanks

    • KY

      Kyle York

      over 3 years ago #

      1/2) Customers and revenue. I know this sounds obvious, but the issue I see in startups too often is that they think "product - out" not "customer - in." It really is about driving business value for the market and survival is assured. Most often the case for technology/product focused founders.

      3 Share
    • KY

      Kyle York

      over 3 years ago #

      3/4) Scaling is incredibly hard. The skills required to build an early stage startup aren't the same as a fast-growth more established one or even moreso a $100M ARR SaaS business like we are today. I think the biggest key is understanding that not everyone will be a fit for the full journey and personally adapting is hard. Once you learn that, focus on strengths individually and for the business, you'll be in good shape.

  • SA

    Shaker A

    over 3 years ago #

    Hi Kyle,

    Excited to have you here

    1)How do you look at competition, specifically when your going up against bigger, and better funded competitors that have been there longer than you? How does that affect your strategic plan, if it does at all?

    2) How do you look at hiring? Can you talk about some of the mistakes you've made hiring (and also seen others make)? What have you learned about hiring A+ talents?

    3)How do you look at balance in your professional and personal life? When it comes to work, how do you decide what you have to work on today(i'm sure you have alot of fires to put out everyday)?

    Looking forward to learning from you!

    • KY

      Kyle York

      over 3 years ago #

      3) Family is the most important thing in my life. It's as simple as that. Major sacrifices are made to scale a startup and put in the grind we need to do to ensure success. For me, that's never my family or personal happiness. Sure, other things, but I don't believe work is important enough to get in the way of that. :)

      On work - oh boy - it's always a new challenge each day. And there is tons of noise at 400+ people. Far more than when we were quite small. For me, my focus has always been and remains on strategy, brand and major deals. That's my strength and I know it adds value. Whoever controls the revenue, controls the company... so my advice is to always stay close to that.

      • AA

        Anuj Adhiya

        over 3 years ago #

        re: Importance of family.
        I read somewhere that when starting up you have three variables - the startup, your health and your family and you can only have two at any point in time.
        Do you believe that is true from your experience?

        If not, can you talk about specific things you've done to be able to balance all of these things that neither suffers from having your attention?

    • KY

      Kyle York

      over 3 years ago #

      2) "It's the people." --> this is what my father has always said my whole life as it relates to everything. It couldn't be more true in a business and mostly in a startup where it all is all about complementary parts. Don't hire other YOU's, hire around you for your weaknesses so the sum of the parts become a big strength.

    • KY

      Kyle York

      over 3 years ago #

      1) I believe in coopetition. It's a tricky thing for competitive individuals to embrace, but for a market to exist there must be leaders and followers. I've written about this at my blog https://medium.com/@kyork20/markets-aren-t-won-they-re-lead-d4d987a1bdb4#.ww0hz03vy

    • KY

      Kyle York

      over 3 years ago #

      Re: Balance. Health. That's been a rollercoaster. But I'm trying - all you can do is try to stay fit. :)

      • KY

        Kyle York

        over 3 years ago #

        I'm just kidding. I'm not that unhealthy. Things just ebb and flow. I try more than ever to take my time off too to recharge. It's the beauty of having a large team and big company at your back.

  • MM

    martín medina

    over 3 years ago #

    Kyle,

    Thanks for coming and doing this AMA. Very excited to have an expert in strategy with us today.

    What does your day to day look like as CSO?

    How do you separate the process of strategy formulation with strategy implementation? How do you revise and adapt your strategy if you identify issues?

    • KY

      Kyle York

      over 3 years ago #

      1) My day is different every day. It's one of the main things I love about my job and I try to operate in what I like to call a "flow-based" work style. I work closely with product management, marketing and sales leadership on strategy and execution support. That's the internal stuff. But, most of my day I'm on calls, in F2F meetings with partners (existing or potential) and major strategic customers. I also spend a lot of time following the trends, reading and learning about what's next and sharing that with the teams. My job is about being an encyclopedia of the business, market and customers. If I do that well, we do well.

      • AA

        Anuj Adhiya

        over 3 years ago #

        re: following the trends, reading and learning about what's next - what resources have you found to be the best in keeping you up to speed?

      • KY

        Kyle York

        over 3 years ago #

        I am on Twitter non-stop. That's my favorite source. LinkedIn has a lot of good content now. For me, it's also about the work I do in the startup community. That's where innovation really happens, so AngelList is a big help.

    • KY

      Kyle York

      over 3 years ago #

      2) This is a big challenge. You must always adapt and change. And you won't always be right either when it comes to strategic direction, so quick iteration is critical. Strategy isn't a set in stone thing. If it isn't always changing, you're doing something wrong and aren't seeing far enough into the future.

      • KY

        Kyle York

        over 3 years ago #

        Ask your customer and your people. It's most often times the casual convos that lead you to that conclusion. Oh, and also when revenue isn't flowing in as planned.

      • AA

        Anuj Adhiya

        over 3 years ago #

        Are there any common patterns in terms of leading indicators you've seen that tell you that you need to (start to think about) a change of directon?

  • AL

    Arsene Lavaux

    over 3 years ago #

    Bonjour Kyle,

    Looking forward to great learning from you.
    Thanks for doing this AMA.

    A few questions for you:

    1) As you scaled from 30 employees to nearly 500 in just 8 years at Dyn, what was your biggest growth challenge? How did you solve for it?

    2) In early stages, did you let the product-market fit discovery influence the way you positioned Dyn from a branding/messaging standpoint? If so, could you shed some lights on how?

    3) Do you believe the Internet will become artificially curious beyond becoming more artificially intelligent every day?

    Merci beaucoup.

    • KY

      Kyle York

      over 3 years ago #

      1) I mentioned this earlier, but I think it's really about the right team at the right stage. That cultural alignment and interpersonal fit is really important to scale. I think for me something clicked early that I needed to really evolve and adapt myself to the next level of growth, BEFORE we were there. Once I figured that out, polished up, I realized that I could get past the challenge of trying to be yesterday's best version of my business self, but evolve for what I could be in 20 years, every-single-day.

    • KY

      Kyle York

      over 3 years ago #

      2) Sure did, but we also sort of let our marketing position pull us forward a lot. Say you are something and you'll race hard to become it was our unspoken model. I always say Dyn was IoT before IoT, SaaS before SaaS, IaaS before IaaS and Internet Performance before people thought about it as a problem to solve. Stay one step ahead, be able to have the swagger and tech to back it up, and run hard at catching up product wise.

    • KY

      Kyle York

      over 3 years ago #

      3) That's a very cool concept, Arsene, and I do believe that it'll develop holistically and with new technology innovated upon it to be more predictive, more recommendation oriented and more two-way in it's nature. Today, we're "on" the Internet and someday we'll all be "in" it. I wouldn't be surprised if we're all assigned with an IP Address. :)

  • KS

    kuldeep sharma

    over 3 years ago #

    Hello Kyle

    Thank you so much for your AMA.

    what is biggest challenge you face as a CSO. also need your expert advice on how strategy, execution and marketing perfectly work together?

    Regards

    Kuldeep

    • KY

      Kyle York

      over 3 years ago #

      Great question, thanks. The biggest struggle I face is what I like to call "end-to-end execution" of the strategy we've set forth. Are we moving at the right pace? Are we iterating enough? Are we timed right in the market? My expertise isn't as operational or execution oriented as others. It's a real challenge to get a company of our size all completely aligned, efficient and results driven.

      On your second point. It's all about communication, collaboration, empathy, and moreso conviction in the decision making. That is what leadership is all about.

      • AA

        Anuj Adhiya

        over 3 years ago #

        re: a real challenge to get a company of our size all completely aligned, efficient and results driven.

        What strategies, processes and/or tools have you found to help raise the odds of alignment etc occurring as expected?

    • KY

      Kyle York

      over 3 years ago #

      Collaboration and communication tools help. We're a google apps, slack, jira shop. I think being accessible and quick to respond across the board is most critical.

  • AT

    Atanas Terziev

    over 3 years ago #

    Hey Kyle,

    Thank you for your time!

    Having in mind your intense schedule, what room do you leave for personal development and how do you invest that time?

    Cheers,
    Nasko

    • KY

      Kyle York

      over 3 years ago #

      Thanks, Nasco, great question. I'm ALWAYS learning. Inside the walls of the day job and out. That's why I spend so much time advising and investing in startups. The secret is that I'm a sponge for information at all times and always look to unique sources to get it. My first CEO taught me to always be one step ahead of my peers, customers, partners, market, competition and I try to do that. To me, that is personal development at its core.

  • RB

    Ry B

    over 3 years ago #

    Kyle,

    Great to have you here!

    1)Can you talk about the top skills that you think a founder needs to have to succeed?

    2)How do you go about empowering employees? What does empowerment look like at Dyn? And how do you make them take on that ownership mentality (even if there is or isn't an equity distribution plan)?

    3) What do you think are the top skills/traits that a manager needs to have to bring out the best in their employees?

    Thanks for doing this.

    • KY

      Kyle York

      over 3 years ago #

      1) A great founder needs to be a great leader and communicator of vision. A leader of their craft, most importantly. Important to be focused as a founder on strengths and be self-aware enough to recruit and built a great team around you.

    • KY

      Kyle York

      over 3 years ago #

      2) Empowering employees is all about trusting them. My teams have always had tons of rope, and all I ask is that they have a good pulse for pulling me in and communicating proactively. We try to create goals, align people, and our variable incentive plan is there to reward results.

    • KY

      Kyle York

      over 3 years ago #

      3) Hire for your weaknesses and better than yourself. It empowers, lifts up, and create a T-E-A-M dynamic that can't be beat.

  • ES

    Edward Stephens

    over 3 years ago #

    Hi Kyle,

    Can't wait to hear from you - a couple of questions from me:

    1) How do you keep hiring good talent when scaling from 30 to 500 employees and how quickly can you feasibly implement this and create well structured teams and reporting structures? What practices do you think big companies need to be better at (e.g. data transparency)?

    2) As an expert in global Internet and technology trends - what trends are you keeping an eye out for over the course of the next 2, 5 and 10 years?

    3) (A hypothetical question relating to the last). If you ran a hedge fund trading in sectors that were going to benefit from the rise in robotics, automation etc - which areas would you focus on? (E.g. suppliers of Lithium batteries of GPU processors).

    I can't wait for your answers.

    • KY

      Kyle York

      over 3 years ago #

      3) I have no clue!!!! HA! Robots are taking over the world!

    • KY

      Kyle York

      over 3 years ago #

      1) We're still learning here. Being HQ'd Manchester, NH, we've become a real employer of choice North of Boston. This has been very helpful for us as we've scaled, but it's hard. A joke was made yesterday that early on you got hired because of who you knew and the risk you were willing to take at our starup, while today you get hired for merit, experience, resume, etc. I think this is a tricky balance for all companies of all sizes bc for me it's all about working and running hard at your goals with people you trust. The best hires fit both at this stage.

      • KY

        Kyle York

        over 3 years ago #

        2) I focus on B2B enterprise software... so I pay attention to any market that the Internet can disrupt. At Dyn, this is great alignment as we try to improve the performance of the Internet for everyone. I've been very intrigued lately on volatility of the Internet and also how regulations and controls get broken by a flatter world.

    • KY

      Kyle York

      over 3 years ago #

      More on Entrepreneur today on the flatter world trend: https://www.entrepreneur.com/article/281183

  • MS

    Mark Savchuk

    over 3 years ago #

    Hello Kyle,

    How on earth do you manage to keep 500 people productive? I've worked with small teams (so far) and I've seen that wrong communication can lead to disaster.

    How do you manage to stay focused with 500 people? How do you make sure that everyone knows what they are doing and how do you maintain the transparency in an team that big?

    Thank you,
    Mark

    • KY

      Kyle York

      over 3 years ago #

      Great question, Mark.

      1) Wait, all these people aren't hired actors?! It starts at the top. We've got a big vision here "To be the company connecting people, content and commerce through a single global Internet." so I challenge our people all the time to speak up if what their working on doesn't get us a step closer to that. Leadership is about setting the vision and communicating feverishly to keep people aligned. It's not easy, always efficient, or always fun... but having great mid-level leaders and individual contributor leaders is most key too. Leadership isn't about title, it's about action. That's how companies scale.

      3 Share
      • MS

        Mark Savchuk

        over 3 years ago #

        "1) Wait, all these people aren't hired actors?!"

        ahahahaa, laughed so hard, got a poke from my colleague, thanks for the reply Kyle :)

  • DH

    Dani Hart

    over 3 years ago #

    Hi Kyle,

    So great to have you here today.

    As you grew from 30 to 500 employees in 8 years, I'm sure you experienced a lot. How would you explain the evolution of your company's culture throughout those 8 years?

    Looking forward to what you have to say. Thanks!

    • KY

      Kyle York

      over 3 years ago #

      Thanks for the question, Dani. I'd say the culture has "matured." I was joking yesterday that we have "old Dyn" and "new Dyn" and what I mean from that is maturation. Back in the early years, we were so scrappy, unorganized, running mad - and it worked - we crushed it. Today, there is a lot more process, structure, oversight. We didn't have a board or investors for my first four years here and 11 years of the company and we're still crushing it.

      So, a lot changed from "old Dyn" and that's not for everyone. It's hard to accept and quite different.

      Reality is, with a focus on building a long-term sustainable company, we needed to step up our professionalism, structure, leadership etc., but I think we're just now trying to get some of that old mojo back. The pendulum swung too far. You don't want to over correct and I know we've done that here at Dyn and alienated a lot of people who we've lost or are still here. As a leadership team, that self-reflection is there, and we're doing all we can to find the balance required.

      Hope you appreciate my honesty here. It's something I obsess over and am becoming more vocal about recently. So, maybe I'll share this internally. ;)

      • DH

        Dani Hart

        over 3 years ago #

        Thank you so much for the honesty! I can see how the pendulum swings and people would feel alienated. From an employee point of view, I find transparency from leadership to be one of the most important drivers of company culture. Have you tried any form of this at Dyn? How do you source employee feedback as you navigate these changes?

      • KY

        Kyle York

        over 3 years ago #

        I try to do as many 1:1's as possible and be as transparent as possible. This is not always the case across all departments or the entire company. It's hard. We've done a variety of things. A yearly survey, suggestion boxes, 360 reviews and more. Things come and go, but important to always try new things.

  • TN

    Tri Nguyen

    over 3 years ago #

    Does Dyn have a dedicated growth team? If yes, how is it structured organizationally? If not, why not?

    • KY

      Kyle York

      over 3 years ago #

      We don't and never had. I think a lot of people brand their digital marketing team or SDR group this. I think everyone in a fast-growth company should be committed and dedicated to growth and accountable to success. It's why we've always had a company wide bonus incentive plan tied to ARR and cash mgmt or profit. I advise startups to do the same to align everyone towards milestones, targets and success.

  • BW

    Brand Winnie

    over 3 years ago #

    Hey Kyle,

    You're the man. Thanks for doing this.

    From the startups you advise, have you ever come back with an idea or learning that you've been able to apply at Dyn? If yes, can you talk about one high impact example and what the outcome was?

    • KY

      Kyle York

      over 3 years ago #

      Thx - I'm humbled. Of course, I have. I learn so much from not only the companies and their business models, but from the founders. They are all so unique, smart and ambitious. One example that comes to mind came from interactions with the CEO/founder of http://datanyze.com, Ilya Semin (I'm on the board), who is obsessed with data and built his entire company with data as a core foundational competency in their tech platform, but even in the way of running the business. At Dyn, we now are VERY focused on internet traffic data and have the world's best data set for it.

  • RO

    Ryan O'Hara

    over 3 years ago #

    Hey Kyle,

    How'd you guys pick your early enterprise verticals? How'd you guys pick who to target? Was it just based on your first set of Dynect customers, or was it based on a hypothesis that stuck?

    • KY

      Kyle York

      over 3 years ago #

      Great question, Ryan. It was very well thought out based off of one key point. What common value proposition, repeatable use cases and characteristics exist across 3-5 verticals. For a company whose technology horizontally scales across any vertical, it is important to find the focus that best represents the market. For us, it was a simple question: "What verticals most require a reliable and fast web presence?" From there we were able to select key verticals, create use cases, reference accounts, testimonials etc. and go big. This was 2009 - SaaS, Ecommerce, AdTech, Web 2.0, Media - were the winners and we then went out and won 37signals, Zappos, AudienceScience, Twitter and Mashable as lighthouse customers to take down these industries.

      3 Share
  • AA

    Anuj Adhiya

    over 3 years ago #

    Hey Kyle - super to have you on!

    When do you think its appropriate for a company to have a dedicated CSO position? What signals or triggers should indicate that its time to think of having this role within the organization?

    Also, if you're ready to go hire for this position, what should the company be looking for in terms of skills, experience etc from whoever the right person might be to fill this role?

    Thanks!

    • KY

      Kyle York

      over 3 years ago #

      Nice question - that to me is completely dependent on the talents and skills of your leadership team. I, personally, grew into this role. I was originally hired as VP, Sales & Marketing, then CRO, and now CSO. On the surface, I've always focused on strategy, brand and major strategic engagements. As long as you have that in your company, from the CEO or a CSO or a VP BD... you'll be in great shape.

      If you're going to hire one - be sure they are an industry and market expert, can do major deals, understand your business model cold, have serious vision, can get technical, and can handle it. It's a tough job!

      • AA

        Anuj Adhiya

        over 3 years ago #

        I have no doubt it's a tough gig - I can't even imagine the scope and weight of your responsibility!

  • AA

    Anuj Adhiya

    over 3 years ago #

    One more:
    For a company your size, how do you prevent a culture of internal politics and fiefdoms?

    I've seen this from personal experience in a few cases where once the company got to a certain size, this became an issue - but only to those not in executive/managerial roles. Everyone else (at the top) appeared to think things were ok making it very hard for those at the bottom to even be heard or taken seriously just because they didnt have a title/long experience within the company.

    • KY

      Kyle York

      over 3 years ago #

      I think trying to create a culture where culling out that BS and trying to stop it before it starts is important. It takes proactive leadership that listens and sniffs that out. It does happen though and overtime at Dyn those people operating that way haven't lasted. I certainly hope we continue to try and focus first and most on the outside game of customers, growth and revenue.

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