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Ticketing and IT at G2 With Garrett Cook | Where’s The Any Key? Episode 4

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®

The guest joining me today is Garrett Cook, who is the Manager of Information Security and IT at G2. 

A Bit of Background on Garrett Cook

Garrett: I started at G2 to build up their information security program. They needed IT help as well, so I have taken on both of those roles at the company. 

Before I got to G2, my background was in sysadmin work. I’ve worked in several companies of different sizes, industries, and setups, and it has been a long road to get to G2, but I’m glad I’m here.

For a bit of overview of the company I work for now, G2 is a software review platform. So if you use any sort of software in your business, like Salesforce® or JumpCloud, you can go on our website and either write a review or find reviews. We encourage people to tell us what they think about the software they’re using, because we as consumers rely so heavily on reviews for the products we’re considering purchasing, like with Amazon®.

Often, unless you know someone who has used a piece of software, the only other source of information you have regarding functionality is from the company itself. G2 fills that gap so you can ascertain accurate, unbiased information on the software you’re considering. 

What Does the IT Team at G2 Look Like?

Garrett: I’ve got two guys who work at the service desk; one works here in Chicago and one works at our Bangalore office. I handle most sysadmin tasks, like endpoint configuration and networking, but I’m training the other team members to take over some of the responsibility I currently handle. 

Ryan: I always like the idea of being about to train team members at the tier 1 or tier .5 level. It gives them exposure to higher-level IT demands.

Garrett: Exactly, I don’t want them to ever feel like they’re stuck in their current role and they can only function within the exact parameters they’ve been given. I always want newcomers to be able to explore other interests, and I want to help foster that idea of growth for them. 

Ryan: That’s always a good feeling knowing you’re encouraged to grow in your role. So do you have support on the information security side of things, or is it just you?

Garrett: I have one guy who works in a security operations role, so he works on antivirus enablement, security log monitoring, and sometimes he interacts with our customers if they questions about our infrastructure security or general security processes in the company.

What Department Do You Fall Under?

Garrett: When I started at G2, I didn’t know who my boss was. I was interviewed by several people who could have all been my manager, but I was sort of walking in blind. Currently, we fall under the Corporate Department, which houses a number of miscellaneous teams. So in my department, we’ve got finance, accounting, legal, office operations, and IT and information security — which is all managed by the CFO.

Ryan: I’ve always found it interesting to understand how different organizations categorize their IT departments.

Garrett: I hope to one day separate and become our own department, but for now this is great. We report directly to the CFO for any purchasing or budgeting requests, so the CFO cares about IT but isn’t heavy-handed in our day-to-day operations. Functioning this way allows us to have freedom.

Ryan: That’s a great spot to be in. I’ve been spoiled in my IT career where my department’s always been high up the chain. That being said, I’ve always made it a point to come with evidence to support my requests, which makes it easier to get approval.

Garrett: It’s good for IT professionals to have relationships built around reporting because it gets them in the habit of being able to effectively speak with non-technical folks. That’s something I know a lot of us struggle with, so having to do that regularly really sharpens those skills. 

Maintaining Work/Life Balance in IT

Ryan: In IT, a lot of people feel a need to work insane hours and put in more than their fair share of time into projects just to feel like they’re needed or necessary.

Garrett: I see a lot of unspoken pressure to work outside of standard business hours when it isn’t required. I think that stems from the fact that IT departments are frequently understaffed or lacking budgets. It contributes to this mentality of “we need to work all hours of the day.” 

For me, I encourage my team to not put Slack® or email on their phones and work the hours that suit them best. Maintaining that work/life balance is really important to me.

Ryan: I think part of where that comes from is that IT — in the vast majority of cases — is a cost center. What we strive to do is make the business function more efficiently and increase productivity. That can be a lot harder to track, and what a lot of managers and companies do when viewing IT is that they look at productivity. They say, “Okay we’re sinking all this money into this department. How can we get the most productivity out of it?”

I think that mentality passes on to the workers, and I will fully admit that I have been guilty of that. I have been the one-man IT shop so many times where I was on call 24×7. But we don’t need any more people burning themselves out in the IT industry.

Managing The Responsibilities 

Garrett: In addition to our IT responsibilities, we are also responsible for physical security, such as badge readers and camera systems. We also manage our sound masking system. So really we have an ever-growing portfolio of responsibilities. 

As a manager, I make sure to clearly emphasise what my department can take on and what we can’t. That way our list of responsibilities isn’t just constantly growing, and we’re taking on things that we can handle. 

Ryan: There are only so many hours in the day. I have to make sure I draw those lines. At our organization, everybody has standing desks. If there was a problem with a desk, I had tools handy to help. But as we’ve grown those little fixes have become more time-consuming, and just because it has electricity doesn’t mean it’s IT.

Garrett: We faced that same issue with our organization’s motorized standing desks. Our headquarters moved in August, and of course there were some issues with the new desks. Our troubleshooting was to essentially check if everything was plugged in, which luckily fixed 90% of the issues. No one really comes to us anymore, and I’m glad to be able to pass that one off to the office team.

Ryan: I get that need to be helpful, but as a department you have to draw that line eventually. Otherwise you’re going to end up overwhelmed and overloaded with tasks.

Garrett: And you typically can’t offload any of those responsibilities once you’ve taken them on. 

Handling Internal Requests

Garrett: Our IT team only handles internal requests; we have a whole separate team that works with our external customers. On the information security side, we do engage with our customers as needed on security-related topics.

In regard to end user ticketing requests, we became an early user of a platform called Halp, which integrates with and lives primarily in Slack®. G2 really revolves around Slack, so Halp was a natural fit for us. We were able to keep people using a platform they were comfortable with and not force them to learn and use a separate system just to get help from us. It’s been so successful that I’ve gotten six other teams to use the platform for their own purposes.

Ryan: JumpCloud is also a customer of Halp. It made that relationship between the end user and the IT team easier.

Garrett: There are so many barriers between the end user and submitting a ticket. The best benefit of Halp to me is we can keep the entire ticketing process in Slack.

Ryan: G2 runs primarily on macOS®, which is interesting because the common thought in IT is that Macs are terrible, and everything should be run on Windows®. What are your thoughts on that?

Users and Their Machines

Garrett: My entire career before G2 revolved around servicing and running Windows. But now that I’ve seen this other side of the user experience, I honestly never want to go back to a Windows-only shop. There is a higher upfront investment with the buying the computer and the warranty, but for most use cases the performance is just unbeatable. 

Also, from a security perspective Apple® —  since they do tightly control their operating system — really builds a security-centric machine. There are a lot of built-in controls that help you secure the endpoint. 

Ryan: Microsoft® had to design their OS to work on a number of different types of hardware. In  contrast, macOS only goes on Apple hardware. 

I started off primarily working with Windows, and I think a lot of the resistance comes from the adjustments IT pros have to make in order to shoehorn Macs into a Windows environment (which is never fun). 

When you build a Mac-centric environment, you have built-in tools to manage them. I’ve been on a big push to standardize us to Macs whenever possible. On the development side of things, our platform works on Mac, Windows, and Linux®. Our development team has to be able to test on these different OSs, and if you have a Windows or Linux machine, you can’t really run Mac VMs on them. But if you have a Mac, you can run Windows and Linux all on the same machine. It makes more sense to have people work on Macs, but sometimes developers will be developers and that they want their Linux boxes. There’s only so much pushing I can do.

Garrett: At G2, you can only get a Windows or Linux computer if it’s an absolute necessity. We have about 500 Macs and probably 10 other devices.

I think a lot of our IT peers’ experience with Mac came years ago. MacOS has rapidly matured in ways that I haven’t seen from any of its competitors. Apple has made it a lot more functional to be able to service an enterprise.

Changing Perceptions

Ryan: There are a lot of stereotypes that apply to the IT industry; is there any sort of reputation that you feel has been earned? Is there anything you would like to see changed?

Garrett: One of things that I’m really passionate about changing the perception around is that IT departments are seen as insular or antisocial. I really think that having good relationships and being able to speak with people is just as important as having a technical perspective. I think there’s been a negative perception around IT in the business world, and that is something that I think that we really should change.

Ryan: I think of IT as driven by customer service. We’re working in a support department; going out there and building rapport with our end users makes life a lot better. 

Garrett: If people feel as if they can’t come to you (maybe they’re embarrassed or don’t know where to go or what to do) the issues are going to remain unresolved. That’s one of the biggest benefits of having that relationship with your end users — you can resolve situations easily. 

Garrett: When I came in, G2 had never had anyone in a technical role. In addition, I had never worked with a Mac fleet. Also, all of our software SaaS-based; we have no on-premises servers or storage. 

That was the complete opposite of what I had worked with before, so it was a total mindset shift for me. I had to be able to look at things in a new way, and now that I’ve seen the other side of things I don’t want to go back. 

On the security side, we are a marketing technology company, so we do handle confidential data. Being able to understand privacy from a business perspective, and understanding the regulations surrounding that is a constant challenge.

Ryan: With regulations, like those enforced by GDPR, there are people watching you to make sure that you’re handling that information correctly. I can definitely appreciate where you’re coming from there.

Thanks For Tuning In!

Ryan: Thanks for tuning in to today’s episode, and thank you to Garrett Cook for joining us. 

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.

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