Ask Me Anything with Daniel Issen, YapStone Chief Technology Officer

In April 2015, industry veteran Daniel Issen joined the YapStone management team as Chief Technology Officer. With Daniel’s past experience leading teams at Amazon, Google, PayPal and eBay, YapStone is very excited and fortunate to have a technology and payments expert leading our growing engineering and product teams. With only a few weeks under his belt, we were curious to sit down with Daniel for our version of an “AMA” (Ask Me Anything) to discuss his perspective on leadership, technology, and the payments industry.

As the new YapStone CTO, you will be in charge of recruiting for the Engineering team. What will you be looking for?

Daniel: I tend to look for a depth and breadth of experience, generalists who have broad skills versus specialists who can do one or two things. The characteristics I look for include high EQ’s, diligence, attention to detail, cool-headed and good negotiators, meaning “those who can disagree without being disagreeable.” I look for these qualities across the stack because this is the kind of organization I want to build.

YS_Blog_CTODanielIssen_Quote_01_960x150When it comes to people I hire, my main belief is that I don’t suffer jerks. My favorite interview question to ask a manager is, “What do you do with a genius jerk?” The only answer I consider acceptable is to either amend the person’s behavior or have them find another opportunity somewhere else.

Unlike some technical interviewers, I do not believe in puzzles or brainteasers. I ask questions that force a person to think and I’m not looking for the golden perfect answer. I want to see how they think and take something bigger than they can swallow and break it down to something manageable.


YapStone has nearly 300 employees – yet is focused on maintaining a start up mentality. What does our size and mentality mean to you and your process?

Tackling a project at a big company can be like trying to turn around an aircraft carrier – it doesn’t happen quickly and usually requires an immense amount of effort and work. You might have hundreds of different initiatives that you’re pushing for, years at a time, and only make incremental progress. At a mid-sized company like YapStone, we can focus on smaller initiatives and make a bigger impact on the company. We can affect change in a pervasive way. I want to feel like I can make a bigger impact as well as see measurable success and the fruits of our labor. That really appeals to me and I think the ability to change things is what motivates people to join companies like YapStone.

As CTO, what are your priorities in the first 180 days?

My number one priority is to scale our payments platform and technology team to meet the opportunities and challenges presented by our fast growing business. I have many secondary priorities but they all ultimately roll up to be in support of this one.

What was the first message you delivered to your YapStone team?

We’re going to do great things. We have a strong team, an immense opportunity, and a focused mission. Our challenges are the result of our rapid and sustained growth. This is a great opportunity for all of us.

2015 has been called “the year of payments.” What will be the most decisive elements that will make or break a company in the payments industry?

The most common reefs that people crash their ships on in the payments industry is in the areas of onboarding and KYC – “know your customer”. If you look at PayPal’s point of sale system as a use case, the biggest stumbling block they hit was the ability to get through onboarding. There are a lot of intricacies when it comes to payments. For example, the address of a storefront could be different than the address of the actual business location. The data that we rely on in the payments space could be “dirty,” meaning that its incomplete or inconsistent. As a result, there are a lot of scenarios that make it difficult to get through the onboarding process. This in turn affects the ability to take on merchants or vet new partners, which prevents the ability for a business to grow.



How will YapStone continue to compete in the payments space?

From a competitive standpoint, the payments space is a crowded arena and most of the leading players are competing with each other for similar use cases. There are a lot of acquisitions going on and this consolidation makes it even more difficult for new entrants to compete. In our case, we are tackling a space that is under addressed by technology. We’re competing with the paper check instead of other technology spaces, which allows us to avoid this bear trap of competitive risk. I have seen the industry adopt a broad focus on consumer plays, but I haven’t seen the same degree of verticalization outside of YapStone. YapStone is a leader in this model and we are very far ahead of anyone else in our space when it comes to domain expertise.

Tell us which innovations in the payment industry have piqued your attention?

The innovations that I’ve paid a lot of attention to in the last few years is the big shift in notions of brand in the payments industry. Let me unpack that a bit. Before, when a customer made an online purchase they would “Pay with PayPal”, and PayPal would be the brand they saw. In that way, you’ve disempowered the merchant. This makes sense when there is a small merchant that people may not trust because they can trust PayPal. However, once these merchants grow larger, there is a brand standing between them and their customer.

In the last few years, the payments companies that have emerged are not so motivated to take control of this branded experience and are instead shifting into a role that empowers other brands. For instance, when a customer uses YapStone to make a payment, they see the company we’re powering. By relinquishing this
co-branded experience, businesses are able to grow without experiencing a tug of war with their payment providers.

When it comes to collaboration and how people work, can you tell us which technological innovations you’re most interested in?

Virtualization enables us to do some cool things. I’m a big fan of doing development on branches – yet this is difficult when you have a small number of shared development and QA environments. Virtualization enables every engineer to have their own virtualized data center and run a full stack from a development branch that is isolated from unrelated work. With this approach, handoffs of work can be done via branch names, teams can ensure that everything that is necessary to deploy a system is reproducible from the source, and unrelated work streams are insulated from each other.

Give us a personal insight that most people would be surprised about?

I’ve done a fair bit of Autocross, which is a form of car racing in which drivers compete against the clock instead of other cars. I get to drive with a normal street car on a track and it’s a lot of fun.