Gaining Perspective on Support with Jodi Trautman-Phelps | Where’s The Any Key? Episode 5

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®

Today’s featured guest is Jodi Trautman-Phelps, who is a Customer Support Engineer here at JumpCloud. 

A Bit of Background on Jodi Trautman-Phelps

Jodi: I help all of our customers use our product effectively. That can range from troubleshooting simple problems to very complex ones. I often interface with other team members, such as those in engineering, product, and with sales. Essentially I’m there to support our customers in whatever they need.

I’ve been doing this for a while. I started out back in the day, as most folks in support often do, working at a help desk at a university, which seems like a lifetime ago. I’ve done a little bit of everything, from system administration to quality assurance. But ultimately I keep circling back to customer support because I am a people person. I really like having the opportunity to help customers. 

It’s been an interesting journey to say the least. I’ve done a little bit of external support — via phone and professional services online — and I’ve done internal support. For example, I worked for an aerospace company for a while and I had both walk-ins and a user base of about 250 engineers. I’ve pretty much done it all, I think.

Ryan: We’ve talked a bit about your background and it does seem like you’ve done a bit of everything, which is really interesting. 

External Support vs. Internal Support

Ryan: So obviously you have done both types of support. What’re your preferences and insights when it comes to support? 

Jodi: Ultimately both are about helping people resolve their problems and get their environment up and running. That said, I prefer working in internal support simply because I can do it face to face. However, I think in this day and age, especially now in the new normal, face-to-face communication just isn’t possible anymore. 

Now everybody’s working from home, but in situations where I was embedded in the user community it was really easy to connect. That was important to me because that’s a big part of customer success; that ability to build relationships and understand what my customers need. This includes knowing what they’re working on, what their workload is like, what their problems are, what their deadlines and deliverables are, etc. Understanding it all helps me balance my workload and pivot as necessary to be the most effective support person I can.

External support is a little more difficult because there’s no tone in emails, so it’s easy to miscommunicate or misunderstand information. Everybody’s had instances in support cases where you just missed the point totally. Video conferencing software like Zoom or Google Meet have eased that issue a bit, but I still think it’s more challenging to establish a relationship. One of JumpCloud’s core values is about building relationships, so the challenge with external support is finding a way to communicate in a way that’s warm, personable, professional, and helpful. 

Though I prefer internal support, you can definitely excel in external support if you put in that extra effort. Once again, one of JumpCloud’s core values is being 1% better each day. So it may be worthwhile to take a little extra time when crafting your email to add a personal touch. For example, you could refer back to a previous case a customer had to establish rapport. 

Most of the time, I look back at case history just to get an understanding — particularly if it’s a complex problem. We keep records of all the cases that have been opened by a customer and looking back at that is not only good for rapport, but also for understanding what kind of technical challenges they’ve had in the past. I generally make it a practice to pop open the account to know what direction I should take with account.

The Reputation of the Industry

Ryan: Those of us in the industry are aware there are certain stereotypes and reputations that we’ve earned. Out of all of the stereotypes, which do you feel has been earned, and if it’s negative, how would you go about trying to change that in this industry?

The Personalities

Jodi: When I started out in this industry, it was common to view technical/STEM personnel as kind of socially awkward. We have generations now that have grown up with technology, and technology in general is seen as less mystifying. But I think one of the stereotypes of those that work in tech is to see them as that snort-laughing nerd with glasses.

The Backgrounds

Jodi: But I think one stereotype I find surprising is that all IT people, by training, are computer scientists, information technology degree holders, or engineers. As I’ve worked my way through my career, I find a lot of the folks that I interact with — particularly those in support — come with a diverse background.

In our team alone, we have somebody who was a former seminary student. We also have somebody who trained as an underwater archaeologist. My undergraduate degree was in art history with a specialization in medieval manuscripts. 

Ryan: I think that’s a very good point. Looking back through my career, the vast majority of IT people I’ve interacted with essentially came in as hobbyists. I’ve worked with people who have degrees in history, music, and sociology. The minority of those held technical degrees.

Jodi: Think about the fields you just named. I knew somebody who came from accounting. These are all positions that require attention to detail, a willingness to research, and a certain amount of intellectual organization. If you look at a person’s underlying study or discipline, it starts to make a little more sense. Of course, it also doesn’t hurt that a lot of those people are sociable. 

Ryan: I agree. My undergrad is in accounting, and when I compare my accounting education to the IT field, critical problem solving is common across both. There’s a lot of critical thinking that goes into IT, but also a lot of creativity. You may not have the ideal tools or may be facing a problem you’re unfamiliar with, and it’s valuable to have the ability to research, to think on your feet, and to look at things from different angles. 

In interviews, one thing I’ve heard come up is that people are finding IT difficult to get into without a technical degree or a boatload of certifications. While it doesn’t hurt to have a technical degree or a boatload of certifications, I don’t think it’s required. When I’m looking at adding another team member, I’m more concerned with how they solve problems.

The Strengths and Weaknesses

Jodi: People with different backgrounds make your team more robust. They bring in different skill sets and strengths that balance out your team and make it very high functioning. 

Ryan: I completely agree. Most of my IT career has been spent as a one-man shop, which is kind of nice, but the downside is that you’re only doing things your way. You don’t get exposed to other ways of thinking or problem solving.

When our IT team at JumpCloud went from one to two, the dynamic changed for the better. Now I have a team member to bounce ideas off of. He can look at what I’m doing and help me understand what my problem really is.

Jodi: I was lucky enough to sit in on that interview, which was quite an experience. I’m glad that we have Noah on the team. I think it’s been good for everybody. 

Handling JumpCloud’s Growth

Ryan: Not only that, but we have a lot to do! Since I started at JumpCloud, the company has more than tripled in size. I was hired on as JumpCloud’s first dedicated IT person, and before me the IT responsibilities were divided up between several people. 

When I started, we were growing at a decent rate, but it wasn’t until about a year after I started that things really started picking up. So I started by focusing on processes. I set up a help desk and later, as I got a better handle on how things were going, I started focusing on automation. 

For example, before automating the process onboarding can take several hours to get everything ready for just one person. Now, 90% of the onboarding setup is done in as little as 30 seconds per person, and it can be done in bulk. 

So once I’d established these processes, I looked forward, anticipating more employee growth so I could make the case for adding another IT person. If Noah had come on a month later, it would have been too late; I would have been completely drowning in work. 

The Technician-User Ratio

Ryan: In the IT field, we talk about technician to user ratios. I have my own thoughts on that ratio, but I want to hear yours first.

Jodi: I don’t think I’ve ever worked at a place where that ratio was in my favor, particularly with embedded or deskside support. I think some of the issue is there’s not always sufficient customer feedback to help management understand. Though, maybe this will change because we’ve become so much better at data analytics. 

I know from previous positions that the customer experience would be vastly improved if we had one more person to help support engineers. Unfortunately, we just never could convince management of it. Sometimes it was because of the culture, so it made the manager look good if he kept staffing to a minimum. Somewhere in my experience, there was a disconnect between what the tech support brings and what support brings for enabling the engineers. That being said, my understanding was the ideal ratio was about 125 users per tech. 

Ryan: Robert Half actually came to a ratio of about 70 users per tech for a homogeneous environment. Seeing a ratio like that is like seeing a unicorn: it’s a great number, but it doesn’t necessarily seem obtainable. 

Looking at JumpCloud’s environment, we’ve got employees using about 85-90% macOS. We don’t have a lot of on-premises hardware, but we host a lot of SaaS applications. Compared to more traditional companies, we have a very technical user base. Essentially, we are developing a product for IT people, so even our sales and marketing folk have higher-than-average technical aptitude.

Jodi: I’m still shocked by that ratio. I was always told it was 125 users per tech! 

Ryan: I find that 70-80 users per tech is an ideal number. It allows you to not only offer desktop support and handle emergencies, but also work on projects that increase the efficiency across your department and the overall business. 

As you said, ratios are never in the technicians favor. It seems like they’re always off of what they should be. I think that’s because, in most organizations, IT is a cost center. Organizations are looking at how they can ring out every last bit of cost-effectiveness out of the money they’ve dumped into the IT department. So if you can show that what you’re doing really benefits the company as a whole, then you have better grounds for getting a more favorable technician to user ratio.

IT Best Practices


Jodi: First and foremost, focus on security. I did work in federal contracting for about 10 years, and security is huge. But make sure your security isn’t at the point where it’s onerous. For example, if you have extensive requirements for password complexity, but don’t allow your community to have a password manager, they’re going to write stuff down or reuse passwords. They’re going to do everything to subvert your security stance in the name of convenience and ease. 

Enforce security to the extent that it makes sense. You’re going to have to carefully consider where your give and take is, so have a good security plan. 

Ryan: Many operate under the common mindset that security always comes at the expense of usability, and that’s something I completely disagree with. I feel that, if you just look at securing your organization on a policy-by-policy basis, it can make usability more difficult. Why I think it’s false is that it’s not too difficult to mitigate those usability issues. If you have really strict password policies, be sure to provide people with a password manager. There are a lot of things that you can do to help with the burden of security. 

You’re there to create a more secure environment for your end users. You can use that to make your case for increasing headcount or for proposing tools. When I proposed that we add our password manager, I listed out the pros and cons, and security was a big part of that list. If we want to prevent people from putting their password on a sticky note under their keyboard or on their monitor, then we need to invest in a way to make it easier to remain secure. 


Jodi: Document everything. Even if you document something informally and throw it in a shared Google Drive somewhere, write it down. Because you will regret it later when you’re sitting at your desk and a case comes in and you say to yourself, “I know I’ve seen this before, what should I do to fix it?”

That is mitigated somewhat with our case management software. However, everybody knows that one support engineer that hasn’t written anything down that gets cranky when you come to them with questions they can’t answer. I keep a notebook for jotting down little things, or sometimes I’ll put a sticky note on my monitor to document later. Everybody hates doing documentation and often thinks, “Oh I’ll write it down later.” 

There’ve been cases in my career where if I’d just taken 10 minutes to write something down, it would have saved me hours. 

Ryan: I really like documentation, so I get sad when we don’t have time to keep our documentation up to date. I’ve also had to deal with the horror that is nothing being documented or documentation that is way out of date.

Jodi: You end up having to reinvent the wheel, which is something IT people don’t really have time for. 

How’s Life Changed For You?

Ryan: For my final question for you, with the current situation going on with COVID-19, how has your job changed? 

Jodi: Actually, we transitioned remarkably fast, which points to sheer agility of our product and our very own IT team. You guys laid the foundation early on, making our organization more flexible as a whole. 

My job has changed very little, other than an uptick in case volume. Everybody else is trying to do the same thing we did in getting everybody working from home effectively. I’ve been trying to take more time with my cases and put more of a human touch in there to check in with existing and new customers. It’s impactful to ask about their health, whether things are okay, or whether they’re healthy. I’ve been doing a little extra to leave the door open so they can ask additional questions instead of just immediately closing the case. In my job, I’ve always tried to be kind in addition to being professional, so I’ve tried to inject a little more kindness and humanity into my case responses. Right now, the world could use a little extra kindness and a lot more tech support.

Ryan: Words to live by, not just in IT. Thank you so much Jodi for coming on the show!

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

So until next time, keep looking for that any key. If you find it, please let us know.

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