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Mission Team Spotlight: Jason Gay

Jason Gay, Director, Cloud Operations

In this ongoing blog article series, Mission Team Spotlight, we interview and chat with our knowledgeable team members about their careers, time at Mission, and trends in their respective fields. 

We recently talked with Jason Gay, our Director of Cloud Operations at Mission. Jason shares his career history working for cloud managed services providers (MSPs), how he entered the world of cloud computing and helped Mission grow as a Senior Cloud Consultant, and now as the Director of Cloud Operations. He also shares some insights on the business value customers can gain from working with an AWS Premier Tier Services Partner like Mission.  

This interview has been edited for length and clarity. 

Mission Team Spotlight at a Glance

Team Member: Jason Gay, Director, Cloud Operations
Cloud Operations (CloudOps)
Boston, MA
Spending time with his three teenage sons and their hobbies (baseball, martial arts, flight school), running to get outside and move when not at his desk
Fun Fact:
Has a degree in radio broadcasting and music production and has been a recording engineer for Grammy award-winning artist Shawn Colvin, Smash Mouth, and Duncan Sheik

How did you come to Mission?
I started at Mission four years before we were Mission when we were still G2 Technology Group here in Boston, and before Great Hill Partners acquired us with Reliam and Stratalux to form Mission. The founder of G2, Glenn Grant, and I used to work together at a previous company, and at the time, I was looking to make a change. I reached out to Glenn, not looking specifically at G2 to get a job, but when I asked if he knew anyone hiring and what I was looking to do, he said, “It’s funny you ask that. I’m looking for that exact role right now.” I came in for an interview with Glen and spoke with him for 5 hours, came back a week later to meet with more people on the team, and then about three weeks after that, I began my role as Director of Managed Services. 

What got you into cloud computing? Are there any key moments along your career path that brought you to where you are today?
My role at G2 as the Director of Managed Services was my first foray into cloud computing. My previous background was in back office IT infrastructure management, managing a help desk and managing professional services teams at other cloud managed service providers (MSPs) I had worked at. 

For about the first year and a half, I struggled in the role because I didn’t have an in-depth grasp of how cloud computing works. I understood it at a high level, but I hadn’t gotten my hands dirty with it yet. I talked to Glenn, expressing that I loved the company but was in the wrong seat. He graciously kept me on, and I switched to an individual contributor role as a Cloud Consultant. That’s when I learned the basics and the ins and outs of cloud computing. I got the chance to get my hands dirty. This transition was around the same time Caleb (SVP, Business Operations & Strategy and SVP, Service Delivery at Mission) joined the company.

Shortly after we were acquired, I found myself doing a lot of cost management work. Engineers don’t always like working in spreadsheets or building spreadsheet formulas. They would rather script and code. I was just the opposite. So in 2019, when Mission decided we would build a cost optimization practice, now known as our FinOps team in our Customer Engagement Group, I worked with a handful of people to build that practice from the ground up. That was a ton of fun for me, and it’s an accomplishment in my career I’m still proud of today. 

After building that practice and being part of evolving our products like Mission Cloud Foundation, I started talking to Caleb about what’s next, asking where I go from here. How can I help the business grow? How can I challenge myself a bit more? Caleb told me about the Director role in Cloud Operations. The more I thought about it, the more I saw myself being able to do it. Caleb’s scope and bandwidth were changing due to business growth, so the Cloud Operations Director role was created to address these changes accordingly. By the time I applied, the role had been vacant for close to a year. Getting the opportunity to come into this role and getting a chance to push my boundaries and limits has been very enjoyable. I’ve been in the role for just under a year now. It is both a new challenge every single day and the same challenge every single day. 

What is Cloud Operations, and why is it important?
Cloud Ops provides support to customers, whether for monitoring, support, remediation, patch management, or backup management, to answering inbound customer requests. In my eyes, Cloud Operations is the support arm of the business. It can inform the big picture and day-to-day operations of a business. Within Mission cloud operations service offerings, we provide customers with a big picture that not even AWS sees. We don’t only work with customers to solve issues but also to learn from them and improve their AWS environments. 

Let’s look at some of our support numbers. For example, last quarter, we had about 6,100 overall support cases created from inbound customer requests or the monitoring tools we use, like New Relic or Alert Logic. Of those 6,100 requests, we only escalated 4.25% of those cases, or about 258, to AWS, which is pretty amazing. 

What do you like best about your role as a Director of Cloud Operations?
The team I’ve worked with at Mission is probably the single best team I have ever worked with in my career. I’ve been working for cloud MSPs for the past 21 years now, and the team we have in Ops is genuinely the most caring group of people I’ve ever worked with. I’ve never worked with a group of people that care so much about their job and take it as seriously as they do while having some fun with it. That’s been inspirational for me. Everyone is here to learn. Everybody’s always looking for a way to improve. We’re looking to solve the problems at hand but are also asking ourselves, how do I prevent that problem? 

What are some of the most common cloud operations challenges you see with customers? Any interesting stories or highlights you can share?
One particular story comes to mind in the situation when a customer not only needs a partner for technical support, but also an advocate when issues need to get escalated to AWS directly. We recently had a customer reach out to us trying to upgrade an Aurora cluster and they were facing an issue with it. Unfortunately, the upgrades kept failing so they reached out to us. We dug into it a bit and quickly realized that this was not going to be something we could complete on our own. We involved AWS due to the backend access to Aurora that was needed. In this particular case, we shifted to the customer advocate role and highly engaged AWS to help us find a solution and work through the issue with the customer.

What is the role of a cloud MSP when it comes to cloud operations? What should customers look for when selecting a cloud MSP for their cloud operations?
I think the role of an cloud MSP is to do whatever it takes to make the customer happy and bring confidence to their choices. Sometimes that means offering nontraditional solutions, and it’s always asking ourselves a series of questions, how can we resolve this issue? How can we show the customer that we’re doing things outside the norm because the issue is outside the norm? How can offering those non-traditional solutions bring value to the customer, and if it works well, how can we expand it to other customers? 

For customers looking to work with an cloud MSP, there are a lot of cost benefits to doing so, but if they’re looking for that, they have to be willing to trust and relinquish a little bit of control. It can be challenging from our side when we’re playing middleman because we act as a liaison between the customer and AWS. Still, we’re providing customers with faster responses than they would have gotten if they had gone to AWS directly. 

Can you tell us anything specific about how Mission approaches cloud operations and customer engagement? 
We are a much smaller group of people who you can develop a personal relationship with. If you open up a case with AWS directly, whether it’s a chat conversion, email, web, or phone-based conversation, you’ll never talk to this person again in your life. But with Mission, it’s very different. There are roughly 40 of us in Ops, and when customers open a case, they’re going to talk to the same people over and over again. Our engineers and customers develop rapport and relationships with one another, deepening knowledge of how their environment works. We document what we can, so we can understand. Beyond fixing what’s broken, Mission looks at the business impact of something being broken. When your support understands the business impact of your issue, that’s incredibly important, something that you don’t get when you work directly with AWS. 

Do you have any advice or words of wisdom for someone looking to get into a similar career or cloud technology?
Find something you enjoy doing. One of my kids is applying to colleges now and doesn’t know what he wants to do. I tell him that he has to think of two things: 1) You have to be happy with whatever you want to do, and 2) you have to think about the lifestyle you want to live. If you’re comfortable living paycheck to paycheck, week to week, I don’t judge, but you have to be comfortable with it. I didn’t realize until after I finished college that I would not be comfortable living the lifestyle of a radio guy. 

I learned that you have to be capable of learning the technology. If you don’t know the tech upfront, that’s ok. You can learn the technology of any job and how to do a specific job. Even if you’re looking to make a career change and you do or don’t know what to do, go into it with an open mind. Give it your all, and don’t be afraid to fail. I can tell you to this day that there are a handful of technical issues that I faced in my career that, 20 years later, still stick out in my head as major teaching moments. Don’t try to be perfect from day one because it’s an unrealistic and unattainable goal. As long as you’re willing to learn from those lessons and not make the same mistakes twice, you can make those changes and progress along the way. 

To learn more about how Jason Gay and our team of Cloud Operations Engineers, Cloud Architects, and Service Desk Engineers at Mission can help you optimize your AWS environment performance and workloads, check out our AWS Cost Optimization and Governance and AWS Cloud Management pages. Mission is an AWS Premier Tier Services Partner. 

Author Spotlight:

Jason Gay

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