The following is a transcription of an episode of our podcast, Where’s The Any Key? Feel free to reach out with any questions you may have in response to this recording. You can find our show on Apple Podcasts, Spotify, and wherever podcasts are available.
Welcome to Where’s the Any Key? The podcast where we talk about anything IT related and even some topics that are IT adjacent. I’m your host Ryan Bacon, the IT Support Engineer at JumpCloud® Directory-as-a-Service®.
With me today is Jorge Herrera, who is a System Administrator at DoorDash®.
A Bit of Background on Jorge Herrera
Jorge: I wear multiple hats, but right now my main focus is on integrating tools. So I work with SAML 2.0 integrations and Escalation integrations for the help desk. I also work on onboarding and offboarding, and assist with any type of project that requires in-depth technical expertise.
On my path to DoorDash, I started off in the civil service industry. I wanted to gain technical knowledge and widen my skill set, so I ended up taking a risk and left that position to go work at Apple® full time as a Genius. I quickly moved up, starting at the sales floor and moving on to the Genius Bar. From there, I left to go work at MTA, the transit system in New York, and spent about a year there focusing on mobile device management.
After taking some time off to travel, I looked at different opportunities and started working at Pinterest®. I was there for about two years, starting at the help desk and moving up to IT associate.
That position opened my eyes to the startup world. I was always working at a more enterprise-type of environment, where everyone had a director and established processes. In contrast, working at a startup allows you to wear multiple hats and learn new tools or systems. Working at Pinterest really opened my eyes to that startup mentality; it’s hands on deck, there’s always someone shorthanded somewhere. At the help desk, I got to implement new tools and see exactly how IT in a startup functions.
Eventually, I knew I wanted to go more toward system administration, so I applied for a position at DoorDash and was accepted as the first IT person in our New York office. As you can imagine, DoorDash had so many needs that had to be met, so for a while I did a little bit of everything. As the company continued to grow, there was opportunity to implement tools for scalability, so I shifted to primarily focus on sysadmin work. I’ve been doing it for about eight or nine months already, and I love it. Every day presents a new challenge or a different task.
IT In a Startup World
Ryan: Like you said, going into the startup world opens your eyes to new opportunities, and I had a very similar experience when I came to JumpCloud. It was the first startup I ever worked for, and I love it. I think everybody should find a position at a startup at one point in their life, because it is a whole different world.
Jorge: IT is so different from what it used to be. Back in the day, IT environments were heavily architected around Windows® machines, and then macOS® environments were introduced. Now companies and startups are hiring Mac admins to maintain those new machines.
Working at a startup, you can discover what you really want to do, what area you want to focus on, and where your weaknesses are. Before working with DoorDash, I never had to build a server rack on my own or remotely push updates to machines. In the standard enterprise environment, we had network engineers in charge of that, but in a startup a lot of the role requirements change as you grow. Somebody had to do it, and I was curious about learning about it, so I signed up for a Cisco Meraki class and got my certification. If I hadn’t gone to work at a startup I would have never received the opportunity to expand my skill set like that.
Ryan: Especially when you come on as the first IT hire. You’re a one-man shop, and people rely on you to do things that may exist outside your realm of comfort. Operating as the go-to IT professional is just a great way to learn.
Jorge: It also helps with understanding the cross-functionality of your team. How is what I’m doing going to affect other teams? When your role requires that you fulfill one specific task, you don’t get the same level of exposure if you were to come work at a startup.
Handling SaaS Integrations as a Sysadmin
Ryan: You mentioned that one of your main duties at DoorDash is to do SaaS integrations, and you have experience on the front line at the help desk. How was that help desk experience influenced how you work with these integrations and rolling out products and applications that could really have an impact on those front line people?
Jorge: Now, as a sysadmin, any time we deploy a new tool I evaluate it from multiple perspectives. How is this going to affect the end user? How will this affect the help desk workers who are going to have to troubleshoot user access?
From a sysadmin’s perspective, I like to look at the tool and see how impactful it’s going to be. That way I can gauge how we’re going to deploy it, and evaluate its scalability so we won’t need so much help desk support as it rolls out.
I collaborate with the team to ensure that the solution we pick is best-suited for our needs. I want it to be a “set it and forget it” situation where we can push it out and not have to revamp it later on. For example, if you’re rolling out a new tool to ten thousand users, you need to be able to make sure it’s scalable and adapts with your needs.
Ryan: I think that getting a grasp of how every party is affected is vital to a successful rollout.
What Does IT Look Like at DoorDash?
Jorge: When I started at DoorDash, everyone operated under the same title of IT support engineer and everyone did everything. Now, we have a help desk team, which has IT individuals at tier 1, 2, and 3. We also have an AB team, a network team, and a system admin team. We also have a system architect role.
Ryan: That actually brings up something interesting. Everybody starts off as IT support engineers, so I assume that means you had a small group of generalists. How is the need to specialize within IT handled as the organization grows?
Jorge: Team members focused on their areas of interest, so we had a specific team member dedicated to new hire orientation, tools integration, or help desk support. Our head of IT made the decision and structured our roles around our interests. As we grow, we plan to reorganize and build our team to suit the needs of the company.
Ryan: I haven’t had the chance yet to chat with someone who’s been through a transition like that. I imagine that it was quite an experience to live through that transition.
Jorge: I’m sure it wasn’t an easy decision for him to make. The company who was growing so fast, it was impossible for 8 people to support over 2,500 users.
Ryan: And when you’re looking at a fast-growing company, a lot of times IT is the afterthought.
Jorge: From my experience, IT operates on a need-to-know basis. If you want to set up your business for success, IT definitely needs to be involved in those conversations.
Ryan: There were times I’d walk by a group of people and just hear them mention something that surprised me. I wondered why I was hearing about something so important in this way, and oftentimes I had to inject myself into the conversation. It is definitely very common in IT.
What Tools Do You Use?
Jorge: We just recently started using BetterCloud, and now we’re migrating from BambooHR® to Workday®. One tool we’ve been using frequently is Halp, which is an internal ticketing system that integrates with Slack®.
Halp has dramatically changed the process of solving end user problems for the help desk. Now we can track and account for outstanding tickets, and are easily able to involve the sysadmin team if needed.
Ryan: Ticketing can be tricky. We’re Halp customers as well, and having that integration between your ticketing system and your company chat system really does help with the workflow and the end user experience.
Tips For Transitioning To a New Role
Ryan: You transitioned from the help desk team to a more back-end role. Do you have any advice for helping your team and end users who are still reaching out to you after that transition?
Jorge: I like to educate the user. So I let them know that I’m not on that team anymore, but that the help desk is there to take care of you. Also, make sure to educate them on how to properly submit a ticket or get help.
Ryan: So I’m interested in your take on the IT industry. Is there a perception or industry practice that you would really like to change?
Jorge: I’d like to change the perception around what IT actually does. People often think IT just fixes computers. We don’t just fix problems, we are building infrastructure to support a business.
Ryan: What we do is so broad. IT uses technology to help businesses run better. Technology is constantly changing and expanding, and as a result IT roles are constantly changing and expanding as well.
That is the beauty of being in IT, you get to learn and develop under these unique challenges.
Thanks For Tuning In!
Ryan: Thank you very much for tuning in, and thank you to our guest, Jorge Herrera, who works as a System Administrator at DoorDash.
Thank you for listening to Where’s the Any Key? If you like what you heard, please feel free to subscribe. Again, my name is Ryan Bacon and I work for JumpCloud Directory-as-a-Service, where the team here is building a cloud-based platform for system and identity management. You can learn more and even set up a free account at jumpcloud.com.
So until next time, keep looking for that any key. If you find it, please let us know.