IT Managing a $5 Billion Ship

Apr 27, 2019 IT management story

Almost a year ago I decided to pursue an IT management opportunity. Within this role I would be able to lead the technology initiatives of a then $4 Billion (later turned into $5 Billion) investment advisory firm and I would be able to build the team of my own department. This opportunity would prove to be one of the most challenging positions I would ever take on. Let me share with you how it all went….

First, I worked with a professional recruiter from an employment agency who scouted me on LinkedIn and sent me a private message to see if I knew anyone who might be interested in a Technology Manager position. I was eager to get out of teaching and to get back to work within the private sector, so I nominated myself as being interested. It later turned into taking some personality tests and completing a mock interview with the recruiter, who proved to be a good primer for interviewing with the firm I would later work with.

Next, I met with the Chief Operating Officer (COO) at the firm. After a positive conversation it turned into a series of smaller interviews with nearly a third of the firm. One of the people I interviewed with told me: “Are you aware that you will be a department of one person?” I confidently said I was aware and was willing to take on the challenge. A few days passed and I was asked to come back for a third interview with the COO, which turned into an offer of an employment agreement that would be good for a year. After serious consideration, I decided to accept the offer. Two weeks later I was starting the Technology Manager role.

Day #1: I was flooded with orientation and meeting with different people within the organization. A good deal of time was spent with the COO discussing the role and the overall technology initiatives of the firm. They personally bought my lunch and I was even allowed to leave an hour early – not bad right? I thought this was good because all the initiatives were bulleted and it really gave me a way to view what was desired on a higher level.

Day #2: I met with more people within the organization to get a feel for the technology needs of the firm. Of these people I remember meeting two interns who gave me a crash course of programming projects that were developed in-house using VBscript macros and very little python code. All this code was stored on a drive somewhere on the network and they had no way of tracking changes. They were rather excited that I came onboard because now they had someone who they could come to with their programming challenges. I took lots of notes because they explained processes, problems they were trying to solve, and it really gave me a starting point of assessing what the internal development needs would be.

Day #3-5 (End of Week #1): I was introduced to the IT vendor and some of their engineers. Internally whenever an employee had a technology problem they would let the COO know about it, which they would try to solve or they were instructed to contact the vendor. Some employees just contacted the vendor directly. Over time it was pretty clear that there was no process or policy in place. Slowly the COO turned over some help desk tickets over to me. I remember feeling very happy by the end of the first week. Over the next couple of weeks I continued to learn.

By End of Month #1: I was becoming a welcomed addition to the team because there was always a technology problem lingering. With every problem was a post-it-note on my desk and it was filling quickly! Problems varied from problems with software applications, phone issues, printing/color quality issues, and even audio/video issues within the conference rooms. I was constantly working on these issues and still managed to keep up with all internal meetings.

By End of Month #3: I was neck deep into trying to keep up with all of the IT Support tickets. In addition, I was involved in a number of bigger IT projects, such as: implementation of a cyber security solution, two new replacement network printers (setting up users, learning to color calibrate them, collect and send meter readings to printer vendor, helping users figure out color issues, etc.), maintenance of conference room equipment, work with phone vendor on any phone issues, and I developed a much closer relationship with the engineers at the IT vendor simply because I was calling them daily. The relationship between the COO and myself was starting to change by this point. They constantly were asking me what the status of where things were and at one time they questioned me on why things weren’t getting done. I made it very clear that I was feeling overwhelmed by how much work I had on my plate and was trying to figure out a way of managing it all. The only advice that was given was to try to analyze where I was spending my time, which meant I needed to pay closer attention of where I was spending my time and to figure out where all my time was going.

End of Month #4: Along with ongoing IT support, project management, and liaison between the different vendors I had a rather large development project dropped in my lap. The intern working on the project was headed back to school in the fall and only had two weeks before he was headed back. They started to build it in VBScript, but I quickly had to take leadership of the project because I knew right away it was the wrong tool for the job. There were many pieces that had to be built: a database layer with appropriate tables, a data API to serve data (offered way better reusability), and a dashboard to display the data (this was an opportunity to show that spreadsheets aren’t the only way to visualize data). It took a lot of time to develop all of these pieces, but one of the greatest challenges I had was that the intern I was working with had to be taught to do things differently (lack of technical skills at the time) and I was constantly being pulled away from the project to work on IT support or the ongoing weekly meetings. Once again the COO was aggravated and the heat was put on me. This was the only time in my career that I was forced to work 8 hours on a Sunday in order to meet a Monday deadline, which we didn’t meet anyways due to some problems in the business logic. It took an additional week to get irons ironed out, but thankfully it all worked out. Somehow during this month I was nominated for an internal employee recognition award!

End of Month #5: Once again I was being questioned why things weren’t getting done. During this month I created a daily journal for myself. In this I wrote down a brief summary of worked on and how much time I had spent working on it. By the end of the month I had a couple weeks worth of data that clearly showed where I was spending my time. Every week I prioritized what absolutely had to get done and I really tried to understand where the delays were or why things weren’t getting done. It was pretty clear that my workload exceeded my ability, so it was pretty clear that I had a justifiable reason to grow the technology department. Using the data I had collected I was able to create two job descriptions: one focused on IT support and the other more developer-focused. I presented these created job descriptions to the COO, but they only sat on their desk for weeks. Later, the firm decided to purchase Workfront, which was a cloud-based project management solution. This added even more work of creating more internal processes of handling requests (facilities, technology, purchasing, etc.), building custom forms, and completing all the training so that it would integrate with existing technology. The project manager pushed this pretty hard and after many training meetings we both would agree that the work exceeded the workload capacity.

End of Month #7: At this point a number of the larger IT projects were being completed. I held 1-2 weekly meetings with the IT vendor to prioritize projects and by this point I had access to their helpdesk ticketing system. It became a daily ritual of reviewing tickets being worked on or where the delays were. Also, it revealed patterns of tickets that were supposedly “fixed” returning, so in actuality they weren’t fixed at all. No wonder my IT Support workload was overextended. After many performance issues – it became very apparent that maybe the firm needed to find a new IT partner.

End of Month #9: By this time the firm gave the IT vendor notice that they were shopping around for another IT vendor. I was involved in creating an inventory of what the technology needs were, researching the IT capabilities of some IT vendors which we would send a Request For Proposal (RFP) to, and reviewing the proposals that the firm received. I completed a SWOT analysis of each vendor and provided a summary to the Project Manager who was coordinating this effort. Eventually we narrowed down the list down to 3 vendors and we interviewed them individually to ask follow-up questions and give them an opportunity to ask any questions that they had.

End of Month #10: The performance of the active IT vendor only deteriorated. As we requested more information from them (like product licensing, disaster recovery processes, etc.) we kept getting pushback from their leadership and eventually it trickled down to their engineers. In this month the firm also decided to do an office remodel project over a weekend, which involved reconfiguration of the office space. This meant reconfiguring the electrical lines, network cabling runs, installing new furniture, laying new carpet, moving technology (computers, printers) in and out, installing new surge protectors in every workspace, cable management, and putting it all back together by the end of the weekend. The IT vendor was willing to help and they sent a team of 4 guys (CIO and 3 engineers) to assist with the technology work. Unfortunately during this project unexpected things happened: the furniture company sent the wrong colored furniture (2 week minimum delay to reorder) and the IT vendor refused to solve problems on their own without me being present. It was very frustrating because I had to work an additional 20 hours extra that week and no extra compensation or bonus was given. The day after everyone returning was a nightmare because many of the cable runs were terminated incorrectly or the cabling in general was a complete mess. Many phones, printers, and computers didn’t work – so the pressure was on to get people up and running again. Sometimes this meant I had to reach out to the company who did the cabling work and having them come back after hours to make repairs. Also, during this month the Project Manager gave their two-week notice. Their successor was someone who was promoted internally and it was unclear if they had a solid project management background. It really didn’t give me a feeling of confidence about the state of the organization.

End of Month #11: A future IT vendor was selected and the information gathering continued discreetly. As they needed information I was responsible for providing them with they needed. It took time and I had to try to fit it into everything else I was working on, but I was pretty excited to see new projects being lined up and being able to work with engineers that shared the same level of concern that I had. Some of them were more specialized, so it was a huge confidence boost of where the direction of the technology was going. The second round of the office reconfiguration project took place and it was a good test run for the new IT vendor. They sent a team of engineers and among them was their company’s CTO, who was very involved in the project and it confirmed my choice of the company when I saw this person on their hands and knees while working. Termination notice was given to the old IT vendor and the clock started on handing everything off with the new IT vendor. Another manager who had been there for years had given their two-week notice, so once again it confirmed to me that there was something really wrong happening.

End of Month #12: With the many ongoing projects came having to coordinate and work after hours to accommodate the scheduling. It was very frustrating because I was sacrificing a lot of my own personal time in order to ensure things were getting done after hours. It got to a point where it was almost expected. During the transition process – new email, anti-virus, and help desk ticketing systems were introduced to the firm. Eventually the new IT vendor had completely taken over. Lots of issues took place and the COO would scold me regularly. I needed some time to think so I decided to take a week vacation to get away from it all for awhile, which was disastrous because when I came back I would only discover that work was uncompleted and was there when I returned. I tried my best to stay on top of all issues by reviewing the ticketing system and keeping up with following up on things. Eventually the COO got access to the same ticketing system and they called me into their office to review all of the tickets. Again I was scolded and I honestly felt like I was an inch shorter just sitting in the chair. In their eyes I was not performing to their expectations and they wanted me to meet with them twice a day to review and report what is being worked on. This frustrated me and eventually I decided that enough is enough. I wrote my resignation letter that night and the next morning I had put it on the COO’s desk. I was asked what it would take for me to stay and I couldn’t even give an answer because I knew I wanted to get out of there.

Last 3 weeks: The first week the COO called a special meeting with the IT vendor to discuss my intention of leaving and to give them an opportunity to ask me for any IT-specific information. They desired documentation and it was on my list of things to work on before I left. The first week I continued to work on IT support and the following week the COO told me not to work on anything else but documentation. I created a lot of step-by-step instructions of anything I did regularly, created system notes of things that I had worked on, and lots of project documentation of things I had planned out but was unable to work on due to lack of time. It’s ironic because I still had to meet with the COO daily, but it was to only report what was done for the day and to help answer any questions that come up before I was gone for good. Also, a project that would have to be worked on in October was quickly brought to life in July. Why? I built it and there wasn’t anyone else there who was familiar enough with it to make the updates that needed to be done.

Overall, there was so much to learn in this position that I had once held. When I first started it felt like the company’s technology was either a sinking ship or one that was lost at sea in the technology waters. My main mission was to try to get things stabilized and for people to see that I was really advocating for them. Unfortunately, the workload exceeded my ability to do independently and my attempt to try to grow my team was halted. The COO fought me time and time again; eventually, it became very clear that our paths were going in different directions. It was tough to say goodbye, but I still wish them well and hopefully the workload situation improves in the future.