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Sales Culture: An Interview With CRO Kyle York

(This Q & A with Dyn Chief Revenue Officer Kyle York originally appeared on

How do you measure the effectiveness of your team? Is it just revenue or are there other important metrics?

At Dyn, we continue to evolve our thinking and focus when it comes to growth and our core benchmarks. At the highest level, we focus exclusively on hitting our sales bookings forecast quarter over quarter, year over year, with an eye on scaling the business in a responsible, profitable way for our employees and customers.

We measure the standard key SaaS metrics to ensure we’re operating within our targets for annual recurring revenue (ARR), cost of sale, cash, customer acquisition cost (CAC), customer lifetime value (LTV), and churn. Most people within the company or sales organization don’t have the perspective on how many growth drivers are in play when rapidly scaling Dyn.

In addition to focusing on revenue holistically, we focus heavily on the channels in which we acquire those dollars: direct sales, ecommerce self-signup, resellers, and integrated partners. Once we land customers, and as we gain more customers each year, retention (or churn) becomes our most important metric. We also focus heavily on the cross sell and upsell opportunities in the business and ensure we have a healthy split when it comes to our product offerings. This revenue diversity leads to a very healthy business.

This is one of the reasons why, as Chief Revenue Officer, Client Services is one of the divisions I oversee. With every major sale, we have a member of our Implementation Team (part of Client Services) on the call with our sales reps. The IS team speaks on behalf of the prospect ensuring that our sales guys don’t offer them anything we can’t deliver on.

Sometimes, this creates smaller deals but it builds trust and relationships, which are our ultimate goal. This also lays the foundation for that longer relationship. Once these customers are aboard, our Concierge organization (post sales support) ensures the best service in our space.

Kyle York talking sales strategy with The Next Web’s Martin Bryant.

When it comes to our sales team, these contributors maintain account management of their clients and work hard to provide a valuable long-term opportunity.

Of course we also measure sales reps on a more granular way (activities, quota, pipeline, forecast), but this gives a high level overview of what it truly takes to evolve as an organization.

What attributes do you look for in your sales hires?

I think the number one attribute I look for is hustle. There is an old quote that “half of life is showing up,” but in today’s business climate, I really think that half of life is hard work. The beauty of sales is that the only person standing in your way is yourself. If you work hard enough, you can be incredibly successful.

Within our sales department, we have a lot of different personalities and styles. We have some people who are your stereotypical smooth talking and slick sales rep, but we also have some of our best reps who are quiet, humble and just incredibly smart. There isn’t one way to be successful in sales, but the common denominator is honesty, passion and persistence.

We look for people who know who they are, and can bring it every day. They also need to be able to pick things up quickly because probably none of them have ever sold our products before.

How do you keep your team motivated?

Money is a huge motivator and there is nothing wrong with that. For sales people, it is a way to keep score. We have a very healthy compensation plan with amazing accelerators that truly reward top performers. If you’re great, you earn great money. We give cash bonuses and prizes to the sales rep that reaches his/her quota first each month or wins another random monthly contest. We also give an additional bonus should he/she do that before the 15th of the month.

At the end of the year we have something called The Ballers Club (often times called the Presidents Club), in which we take the most productive sales people over the course of the year on a great getaway with senior executives. Last year we had a great speaker in Puerto Rico.

But beyond all of these perks, we hire competitive people who want to be the best. That helps motivate them. We also don’t put any golden handcuffs on our talent. We want them to be successful at Dyn and committed. We want them to be loyal. But we are also realists that opportunity might be outside our walls.

We do our best to support this level of ambition and if we can’t retain all talent, make sure they end up close in our networks. We have a very rising tides mentality and believe that success breeds success.

Dyn Sales Gong
The Dyn Sales Gong waiting for the next deal to close!

What are the biggest differences you see between experienced sales professionals and those just starting out?

The experienced sales people have the benefit of knowing how to be successful as a salesperson.  This may sound too basic, but it’s very apparent how someone with experience navigates their job and career. From the compensation plan to the competitive landscape to negotiation to prospecting to closing deals, there is an intrinsic ownership the experienced sales person has that only years, confidence and success allows.

The best salespeople are an encyclopedia when it comes to their products, pricing, competitors, markets, customers, references, and case studies. They can’t be stumped. The best salespeople also are very good at utilizing their resources and knowing what they know and don’t; drawing that line in the sand is a hard skill to master. Because we’re trying to make relationships instead of just sales, our customers are huge ambassadors for us.

If our sales teams are doing their jobs, they should have plenty of happy customers willing to vouch for them. It’s the salespeople that truly weave themselves into the company narrative that see the most return on their time, energy, and effort.

In addition, experienced salespeople have a more developed pipeline and so they can consistently hit quota over many months in a row, while new salespeople are a little more hot and cold.

Do you have an example of how your positive sales culture is impacting your bottom line?

As I mentioned earlier, Dyn is a competitive sales environment, yet not so much that reps forget we’re all on the same team. About eight months ago, a couple of more seasoned sales reps started a mentoring program for new sales people, because they knew they had a lot to offer and could help the company grow in this way. During these sessions, they gave tips and advice on how to sell Dyn’s products and deal with conflicts or barriers.

We’ve found this has dramatically reduced our onboarding time, which is getting our sales people to quota quicker. That is a huge win for us from an immediate standpoint and a future one. Reducing our ramp up time means we can scale more quickly and with more certainty. This allows us to have greater ambition with the goals we set as an organization and it would not be possible if we had a negative sales culture.

Of course, this is always a moving target and we’re always learning and iterating, but we feel as long as we think about the big picture at all times, we’ll be just fine.

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