Leading From The C-Suite: Kyle York of York IE On Five Things You Need To Be A Highly Effective C-Suite Executive

An Interview With Doug Noll

Purpose. Leaders lead. Once you get to the top, you need to be incredibly purposeful and proactive as a leader. At York IE, this means our C-suite must get dedicated time in front of the company. We do this through company-wide monthly and quarterly meetings, empowering all executives to use their voices to inspire and motivate the team. We also rely on them to evangelize the company externally by providing their unique voices and points of view on our industry to the outside world via our blog, social media and third-party publications and events.

As part of our series called “Five Things You Need To Be A Highly Effective C-Suite Executive” we had the pleasure of interviewing Kyle York.

Kyle York is co-founder, CEO and managing partner at York IE® where he sets the vision and leads the vertically integrated strategic growth and investment firm for technology companies. Kyle works closely with entrepreneurs, operators and investors to help them realize their shared ambition to build good companies, create new jobs, grow generational wealth and impact the world.

Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I grew up in an entrepreneurial family. Some of my earliest memories are from my family’s sporting goods store in New Hampshire, where I learned important lessons about controlling your own destiny, doing business with integrity, working hard and being accountable. After I graduated from Bentley University, I went to work at EdTech SaaS startup WhippleHill, then on to executive and C-suite roles at an internet infrastructure company called Dyn. From a small team, we scaled Dyn to $100 million ARR and a nine-figure acquisition by Oracle, and my takeaways from that journey — both good and bad — formed the foundation for how we’re helping tech companies grow today at York IE.

I learned that a lot of the institutions that were ostensibly built to help companies grow — venture capital firms, analyst firms, management consultancies, marketing agencies, etc. — were actually hindering them. And I knew there was an opportunity to build an investment and advisory firm whose goals are truly aligned with those of the companies they work with.

Can you share the most interesting story that happened to you since you started your career?

You may remember Oct. 21, 2016 as the day the internet went down. Dyn ran a critical part of the world’s internet infrastructure, and we were hit by the Mirai botnet DDoS attack. Many of the world’s most relied-upon websites were inaccessible for a portion of the day.

But what you probably don’t know is that, just hours before the attack, we signed the letter of intent to be acquired by Oracle. And they hadn’t countersigned yet. Talk about pressure!

I was so proud of and humbled by our response. Every single person at Dyn stepped up, asking what they could do to help. We thwarted the attack and communicated clearly and transparently with our customers and partners, the media and the three-letter agencies that showed up at our office.

Oracle ended up signing the LOI, and they said our response to the attack was actually another selling point for acquiring us.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

It’s not a quote per se, but when I was a kid my mother would always challenge myself and my four brothers on our priorities, to ensure our life was in balance. She called this “the grid,” and she reminded us to make certain all squares in the grid — family, friends, school, sports, girlfriends, community, clubs — were given the attention they deserved. Back then, I annoyingly rolled my eyes, defended my imbalanced behavior and shrugged, but as an adult this life lesson carries with me.

Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?

I always go back to “Think and Grow Rich” by Napoleon Hill. So many of today’s tech and startup leaders get turned into celebrities because they’ve raised a lot of money or scored these massive valuations. But how many of them are really building sustainable, profitable companies? You probably won’t remember their names in 100 years, but everybody knows the people profiled in “Think and Grow Rich,” like Henry Ford and Andrew Carnegie. It’s got the most proven and practical lessons for achieving what you want — no matter what business you’re in or how you measure your success.

What do you think makes your company stand out? Can you share a story?

At the peak of Dyn’s scaling journey, we were spending six figures a month on agencies, consultants and analysts. I came to realize that these businesses, which are supposed to help other businesses grow, were actually failing us.

If you’re talking to a consultant about helping you with marketing or legal, they’re all hourly-based, and they’re all looking to get as much money out of you in the short term as possible. They operate in extreme silos and are only focused on their functional area. Then, on the investment side, VCs are trying to put as much money into you as possible, for as large of an ownership position they can get, so they can make bigger returns for their LPs, who are their real customers — not you.

This realization was three or four years before we founded York IE, but that was when the seed was planted: to create a combined advisory and investment firm that actually works in the best interests of its clients and portfolio. And that’s what makes York IE stand out.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

1. Principled: “It’s the principle of the thing” was the mantra in my house growing up. When I lay in bed at night, I can still hear my father saying it. What’s the point of winning the world if you lose yourself in the process? Throughout my entire career, I’ve operated under these two guiding principles: be loyal and play the long game. If there’s a great opportunity, but it will come at the expense of my principles, I don’t pursue it. The end doesn’t justify the means.

2. Ambitious: My first job out of college was at WhippleHill. I worked in various sales and marketing roles, and then they asked me to move all the way across the country, from New England to California, to be a regional sales director. I did because it was a great opportunity for my career. Then I moved all the way back to New Hampshire to be “the co-founder the founders never had” at Dyn — another great opportunity. So many friends mocked me in my early 20s for my devotion to my work, but then in our 30s they were hitting me up for career advice.

3. Transparent: Transparency is one of the most important values you can have in a company, and as a leader, it’s up to you to make it part of your culture. For example, when we have our quarterly business review at York IE, it’s an all-hands meeting, and we encourage everyone to speak up and ask questions. Most companies limit QBR attendance to senior execs, and they completely neglect to internally evangelize their vision or business model. But when you’re transparent, you help employees understand and value their work, and that helps foster a positive culture and a successful business.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

I had a lot of career success early in my life. This was great, of course, but it also meant I had to make many hard decisions at critical points in time. A few years after we exited our company to Oracle, when I realized it was time to leave Big Red and leap back into the startup landscape, there were so many available opportunities to consider — not only for my career, but for the careers of my loyal team.

The industry we operate in created pressure for me to decide between being a full-time investor or a full-time operator. The former meant joining or starting a venture capital fund. The latter meant joining an established enterprise, a fast-growth startup or starting my own business. There was no option for a hybrid approach. If I wanted to do both, one would have to be my day job and the other would have to be my side hustle.

But I didn’t feel like picking one would satisfy my career ambition and my hunger to make as big and as broad of an impact as possible on the technology and startup sector. I also wasn’t sure how either choice would enable me to bring my committed and loyal colleagues along with me to do something great together.

So what did I do? I said, “Screw it, I’m building both.” And that is how York IE was born.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?

As a C-suite executive, you are responsible for setting the vision and mission of the business. Where is your company going and why? Other leaders can make very important decisions about how you get there, but it’s up to you to put the company on its chosen path. When you become a C-suite executive, it’s less about the functional area you lead and oversee and more about company building across the board. Your team is no longer just the team you manage, but the horizontal group at the top. And your responsibility is to the entire company.

What are the “myths” that you would like to dispel about being a C-Suite executive? Can you explain what you mean?

This may come as an easy thing to say from the top, but here’s the myth I’d like to dispel: that by being successful and making more money, the work and life of a C-suite executive gets easier. It actually can be the complete opposite. Challenges, headaches, stress, anxiety and mental health issues are all relative, and many times they compound the higher up the ranks you climb in your company and career. This perspective is important for all to realize, as executive leadership certainly isn’t for everyone. Again, I’m painfully aware that this mythbuster point of view will be hard for many in the rank and file to sympathize or empathize with, but heavy is the head that wears the crown.

What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?

Many C-suite executives operate in an ivory tower and are inaccessible. It’s important for leaders to make time to interface with everyone in their organization, down to interns and entry-level employees. This holds true for company-building efforts and day-to-day roles, but also on the personal level. It’s important to connect with your talent. Even when C-suite executives are good at this, they tend to only engage with their functional team up and down the org chart. For example, a chief revenue officer may only spend time in the sales and customer organizations, when they should also spend time with finance, R&D and all other areas to ensure complete alignment on the scaling journey.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

People underestimate how lonely it can be at the top of a company, and how you have to actively combat that to stay connected to your team.

As your company grows, your team will start to think you’re inaccessible — even if you don’t think you’re inaccessible. You need to manufacture environments that make it clear that you’re willing to listen to everybody.

One way we do that at York IE is with monthly “Coffee with Kyle” meetings. I go to the coffee shop across the street with a small group of employees, or Zoom with a couple people on our India team, just to talk and get to know each other better. The agenda is simple: 1. Tell me more about yourself, your family and your life outside of work; 2. Tell me more about your job role, things you’re working on, what you like and what you don’t; 3. Do you have any questions or feedback for me both on the personal and professional levels?

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Be A Highly Effective C-Suite Executive”? If you can, please share a story or an example for each.

1. Purpose. Leaders lead. Once you get to the top, you need to be incredibly purposeful and proactive as a leader. At York IE, this means our C-suite must get dedicated time in front of the company. We do this through company-wide monthly and quarterly meetings, empowering all executives to use their voices to inspire and motivate the team. We also rely on them to evangelize the company externally by providing their unique voices and points of view on our industry to the outside world via our blog, social media and third-party publications and events.

2 . Broad business understanding. It’s one thing to be great at technology or finance or marketing or strategy or sales. That’s par for the course when evolving to one of the top seats in a successful company. The best executives I’ve ever encountered realize that their expertise and skill set dominance is imperative, but that being a broader company builder — doing whatever it takes in other domain areas to grow and scale their company — is what takes them and their company to the pinnacle of success.

3. Self-awareness. It’s important for people to find and focus on their strengths, then build complementary parts around them to realize their vision. I discovered early on that I could be the growth, sales, marketing and go-to-market complement to technical founders, engineers, scientists and other domain experts. As companies grow and their C-suite teams are built out, they need leaders of all functional areas who know how to support each other.

4. A durable and sustainable mindset. So often in the Silicon Valley growth-at-all-costs culture that we’ve grown accustomed to, leaders haven’t had to be as focused on operating efficiently and effectively within constraints. Thinking back to my roots in small-family business, without a profit, you don’t eat nice dinners or go on vacation. Let’s get the focus back on building good, healthy companies.

5. Long-term vision. Nothing truly amazing gets built overnight. Set a long-term career and company vision, be loyal, be patient and play the long game.

In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?

I’d go back to what I said earlier about transparency and accessibility. When an employee can draw a straight line from the work they do to the success of their company, and they feel like their voice is always heard, they develop a deeper sense of purpose and pride in their job. They’re happier and they perform at a higher level, and that’s a win-win for everyone.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Entrepreneurship is a career option for many, but we need to make it even more of a chosen path for the next generation, so they can have a tremendous impact on their world and community. This is why we started York IE. We believe startups are in need of a one-stop shop to help them with building, scaling and monetizing their companies — and that founders and executives need a strategic growth partner on that scary and difficult journey. The current startup ecosystem and venture capital landscape is failing them. Let’s make more entrepreneurs successful on their terms!

How can our readers further follow you online?

Check out York IE on our website, LinkedIn and Twitter, and you can follow me on LinkedIn and Twitter as well.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!