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Greylock’s Head of Technology Manuel Bernal & Ryan Seit Director of IT, Casper

Originally seen on Spoke’s blog. Greylock’s Head of Technology Manuel Bernal and Casper’s Director of IT Ryan Seit on modern IT trends and challenges.

Welcome to Spoke’s very first podcast in partnership with Greylock Partners. Greylock’s Head of Technology Manuel Bernal interviews Ryan Seit, the Directory of IT at Casper.

Show notes are below for your convenience. Make sure to subscribe on Apple Podcasts for future episodes.

Over the past few years, modern IT needs have driven innovation in tools and systems for every fast-growing company. Modern IT is now central for efficiency, innovation, and growth. This is why we at Spoke are introducing a series on Modern IT Leaders. In this inaugural podcast our host Manuel Bernal, Head of Technology at Greylock Partners discusses modern IT trends and challenges with our first guest Ryan Seit, Director of IT at Casper.

This interview has been edited and condensed for clarity.

Manuel Bernal: I wanted to start by asking how did you first encounter modern IT? What do you think when you hear modern IT?

Ryan Site: IT can mean a lot of things, but to me modern IT is being proactive in our support of the teams we support. Expanding on that, ensuring that we’re working properly with our business units and being able to influence decisions. And ultimately, just having a seat at the table when it comes to bigger company decisions.

MB: Definitely. I’ll give mine as well. I think of IT from a very simple perspective, IT needs to be number one, in order for any company to remain operationally excellent. Operational excellence creates the space to be innovative, and that is a huge component of the fun in IT. Creative innovation inspires confidence and trust for an IT team. And of course the goal is to become a business leader within your organization.

MB: I’d love to hear more about your journey at Casper and how you got started, and of course some tricky lessons learned.

RS: Yeah, sure. I was introduced to Casper by my now wife who was working in Operations. She kept mentioning that their Internet service was going down. At the time, I had my own consulting firm, so I took Casper on as a client and they went from “airport expresses”, which I immediately had to rectify, to a more traditional network infrastructure. We moved them to a more structured enterprise infrastructure using Meraki gear (shameless plug: love them, still use them). And as I began consulting with Caspar, I realized there were a lot of management gaps regarding the IT equipment. Long story short, after helping them onboard a new phone system, they approached me for a full time gig and I said sure. The fact that Caspar has a vast amount of resources to invest in IT is to this day very appealing.

MB: I’ve talked to other IT leaders and specifically those in high growth companies and startups. They share a common story; starting as a team of one (and slowly growing) and feeling that they are constantly firefighting. The company experiences so much growth and change and consequently, IT teams feel that they are constantly putting out fires at the cost of tangent progress. In my conversations with these IT folks, we all agree that it is critical to take a step back from your identity as an IT leader and think, have I become a firefighter as a person too? Do I feel as if I’m always firefighting? So let’s discuss this. What did or do you do once you get into the exhausting mode of firefighting? How do you break the cycle?

RS: IT is a process have a strong strategic structure is key to ensuring that there be minimum fires. I can try and break down my strategy into three steps.

  1. Meeting with each business unit and understanding their needs- At one point a lot of our tickets were coming in due to lack of access to services. Upon realizing that we met with all our business leaders and asked them what core services they needed to function. Our tickets significantly reduced beginning that very week.
  2. Stocking equipment- Equipement gets lost and people do not talk about this enough. Once we made sure we had a sufficient stockpile we were able to move towards ticketing tools. Currently, we have gone through a few iterations of our tools.
  3. Automation and a strong service desk- We finally landed on Jira service desk (shameless plug). The reporting and metrics that are included in Jira Service Desk or that we’ve created within Jira service desk help us at a support level especially when analyzing tickets. Through Jira we can effortlessly measure how many tickets are coming in each week, from which teams, who needs to support these tickets, and how we should be routing? We can really grasp the recurring themes, create efficient solutions and enable automation.

MB: I have always believed that the best way to mitigate tickets is by creating and maintaining a formidable ticketing system and creating some type of SLA within the ticketing system. How do you mitigate tickets or route them to the right people?

RS: Yes, Service Level Agreements (SLA’s) become very important when starting to build out the actual headcount in IT, and when starting to develop specific skills sets, whatever the problem that may come up. So the SLA’s that we really care about are our time to first response and our time to resolution. I’m very happy to say that time to first response is at about 87% and time to resolution 95%.

MB: Yes, and adding on to that from my own experience; IT is an operational job and that can get difficult rather quickly. You always need to have a smile on because IT interactions are not only with employees but also customers. So we need to be dependable. We use our SLA’s as a roadmap for the quarter. They help us determine our priorities for the day, week, month, and quarter. Service level agreements are a metric that you hold yourself against. For first response we try to be at 80% SLA’s. If we’re below 80% SLA’s we investigate why we’re below.

So I guess my question is how do you generate your priority levels or time to response?

RS: Yes. So we configured our priority levels in an interesting way. We have two kinds of categories that go into a matrix which then expels out the priority level by urgency and business impact.

For instance, if someone experiences keyboard malfunctions, business is not going to stop. We tweak our priority levels as we go. We triage, and we really try to understand the user story as much as possible.

MB: A Net Promoter Score might ask how likely would you be to use our IT services again. NPS is relatively standard across multiple industries (Apple and Amazon are at a high level). The NPS asks a very simple question and I use it as a metric for my own work. What does your NPS or SLA look like?

RS: Yes, we have a dashboard that shows every ongoing ticket, the workload each person has, number of tickets assigned to each person… And every week we send out the stats. This is our SLA rating for the week. This system enables accountability not only for the team but also accountability for the entire company. We review our CX or customer service, and seaside ratings in addition to our SLA (because we are also accountable to meet the standards that our customers have set). And this whole process ensures that everybody on the team understands what priority levels mean.

MB: Could not agree more. On to my next question, and I would say this is my shameless plug. In the past, I have used various different help desk systems like Zendesk. Currently, I’m using Spoke, and the reason for this is because Spoke is an omni channel. With Spoke I can ask questions on Slack, text, or email. And I think this is similar to what you were mentioning about systems doing intelligent routing. My ultimate IT dream would be to have a one stop shop, a company concierge if you will, where from day one an employee can ask IT questions and develop that IT culture. And to be able to ask at a hotel: where is my room? Or where is checkout? Having that kind of company concierge service, that’s what Spoke provides to us through their intelligent routing system. If you get a question like, what’s for lunch this Friday? It knows to go to our front desk team. So it’s a very simple tool to use, and it is the same concept that IT folks are always looking to instate; leading customer experience and then of course, going beyond.

What are the biggest challenges you predict you will face in the next year or two? And what are the biggest problems you see your team solving.

RS: Right so, Casper started as an ecommerce company and we were just selling online. Recently, we moved into brick and mortar, which introduces a host of new challenges like different levels of security, different domains, different Slack access, GML access…

Delineating the corporate from the retail and splitting the business bit by bit all the while keeping all ends secure. This has been a new concern for us. The rapid growth from opening a store and adding at least 10 employees per store. When you’re opening two stores a week, you have 20 people plus starting a week. IT has to be done at such a rapid pace. Scaling on this level means deciding what is manual versus automated, and what can be automated. And my recommendation to everybody is to automate everything you possibly can. It will make life so much easier. Regarding particular things you can’t document, create a run book! So, automation and documentation are invaluable. And then of course we are to starting to leverage vendors. Leveraging our vendors more and leaning on them for support and help. And this goes along the lines of our retail build.

MB: IT at Casper is in high growth mode. But you still want to have the flexibility to turn out in-house resources? Although in IT, I guess the way to go (in high growth mode) is to outsource in order to receive the help needed in that moment, then scale it, and then once you need to scale down or hit a plateau, kind of wind back down. How do you view this process?

RS: Right. Our vision is to keep IT lean. We do not want to have that massive IT team where we’re just adding headcount every fifty, hundred users. We want to reach the point where we can plateau while leveraging all tools, services, automations and vendors. IT is optimal when it ties the standardized and processes the process.

MB: Could not have said that better. Last question for today: What tool could you not live without right now in your current job?

RS: I would say Bettercloud, it is a fantastic tool. Bettercloud is a SaaS management platform. It was originally built around G Suite management; automating user creation signatures and things like that. I still \think of it as the G Suite for IT. It is the standard foundational glue between all of the services and automation behind IT. Bettercloud acts as a virtual team member capable of building, supporting and creating things for us!


The IT Kit Podcast was originally published in Greylock Perspectives on Medium, where people are continuing the conversation by highlighting and responding to this story.