MLB Winter Meetings: The Best (Worst) Place to Get a Job in Baseball

Terrible photos in this piece provided by the author

The Major League Baseball Winter Meetings is for many fans the most exciting part of the offseason. While the majority of Orioles fans may argue that the most exciting time of the offseason for them is mid to late February, the winter meetings cannot be beat in the sheer volume of news. Free agents sign, trades get made, players most people have never heard of get taken in the Rule 5 draft (probably by the Orioles), and there are more rumors than anyone can keep track of (from both REAL reporters and FAKE reporters). It sounds incredibly exciting, and since the 2016 winter meetings was basically located in my backyard at National Harbor, I absolutely had to go check it out.

Unfortunately, work responsibilities limited my time at the winter meetings to a couple of hours on Day 3. With no credentials in hand, I walked into the lobby and tried to act like I fit in, which was pretty easy, even when one considers that half the people there carried some sort of credential (PRESS/VENDOR/JOB SEEKER/etc). Other than the few who were wearing “Washington DC” themed souvenir shirts, I just assumed that everyone else not wearing a credential was either there for curiosity (same as me) or for baseball related reasons.

High Heat Live! (if you're into that sort of thing)

If you look at the agenda on the MiLB Winter Meetings website, there appears to be a lot to do while there, including several workshops, a job fair, and a trade show. They all sound interesting, and they all cost money (i.e. I didn’t go). For the curious observer such as myself, there really isn’t too much to do. MLB Network was filming “Hot Stove” and “High Heat”, the former of which I may have made my TV debut when I walked behind the set. Aside from a couple of national baseball writers (Rosenthal, Heyman, and Sherman), there weren’t even that many people a casual baseball fan would recognize. However, if you like talking to people, and you like talking to people about baseball, I can see how it would be easy to kill an entire day chatting to a variety of people about baseball, likely talking to a couple who work in a front office. I had little time to spend at the winter meetings, so while did chat with a scout (for the record, he had no idea what the Orioles were thinking) and a couple of current/former Baseball Prospectus writers, I was mainly there to chat with potential job seekers.


Fortunately for me, the majority of job seekers were literally wearing a badge that said “JOB SEEKER”. The winter meetings had always seemed to me like a necessary evil for job seekers. While it would be difficult to think of a better place to find such a high concentration of baseball people in a position to hire, a potential job seeker also has to deal with a large pool of other individuals who are at the winter meetings looking to accomplish the same thing. I wanted to see how their experience had been. To me, the idea of spending days competing with MANY other people for very few jobs, almost all of which demand long hours and little pay seems formidable, although it’s definitely possible, as I’ll get to in a minute.

Walking around and looking at the faces of the potential job seekers hanging out in the lower section of the lobby, there seemed to be a general sense of exhaustion and a little hint of despair. Maybe it was they were overwhelmed, maybe they were tired from 3 straight days of this, or maybe it was a little of both. I was in no place to offer anything to these people other than a couple guest posts at Camden Depot, so I felt fortunate that I was able to find several individuals willing to talk with me. None of the job seekers I spoke to had locked down a job yet, but all seemed to be in good spirits, expressing that their trips had so far been productive (in fact, one person had to cut the questions short when he received a call he had been expecting). That’s a good thing, as some of these people travelled a good distance to get here and make the most of their opportunity. The longest travelled was a guy from California, while another job seeker drove with a buddy of his (also looking for a job in baseball) all the way from Peoria, IL (a 12 hour ride). All were ideally looking for a job in the major leagues, but also realized that they may need to take a position in the minors first (or in some cases, again). Surprisingly (to me anyway), only three of the five people I talked to were looking for a job specifically in a major league baseball operations department (the other two were looking for marketing and facility management positions).

Every single person I talked to was able to set up some meetings while at the meetings, but according to winter meeting job seeking veterans, it pays to have at least one, if not several meetings set up before you arrive, especially if you’re after one of those coveted baseball operations department positions. And while the event had a job fair, the general consensus also seemed to think that the job fair was really useful place to visit, especially if you were looking for a minor league position, but had little or limited benefits for those looking for major league positions. So while it seemed like a trip to the job fair was worth checking out, it is definitely better to spend most of your time setting up as many direct meetings as you can.

The importance of already having established contacts and actually knowing someone appeared crucial for a successful trip, and something that seems obvious if you think the process through. If you were in a position to give someone a job, wouldn’t you be more willing to talk/interview someone you already know rather than a random person that just ran you down in a hotel lobby? Several of the people I had talked to had meetings set up prior to arriving, and as a result they seemed slightly more confident in their job prospects. Like anything, it’s better to be prepared, though that level of preparedness appears to make the whole process more daunting.

The purpose of this article though is not to discourage, but to give a glimpse into the winter meetings experience and hopefully show that this route can be successful. For example, former Camden Depot writer Stuart Wallace took a trip the 2013 winter meetings in Orlando (a 900 mile journey for him at the time), which helped him land a job with the Pittsburgh Pirates as a quantitative analyst in the baseball operations department. Although I did not get to meet up with him during my brief time at this year’s meetings, Stu was nice enough to answer some of my questions via email and provide some advice to those who are looking to take the same path he did.

Stu (whose background is as a neuroscientist, with additional training in biostatistics) only took the trip to the winter meetings once, but he made sure to mention that he supplemented that with trips to other events such as Saberseminar and SABR Analytics to network. He had one interview set up prior to his winter meetings arrival, but cold called other teams while he was there. With so many people in one place looking for the same thing, the key is setting yourself apart from the rest of the applicants. In Stu’s case, he was fortunate to receive advice from a team while applying for an analyst position with them.

"I followed [the advice] to a ‘T’. For me, that meant writing, so I started my own blog and got more active on social media, which led to bigger writing outlets taking a chance on me (thanks, Camden Depot!). I went to as many games as I could (MLB, MiLB, amateur) to get an idea of how to compare/contrast and get a feel for how to evaluate. I talked to scouts (when the opportunity presented itself!) and chatted about how they watched the game. I taught myself R and SQL -- I had some experience with these types of stats/database packages (using different ones for grad school and my job), but felt if I could know these cold, that would help get my foot in the door, since teams have familiarity with these two more so than what I had previously used. From there, I specialized with my writing; my background was in medical research, so I did my best to answer questions regarding injuries or general outlook on performance/pitching mechanics/swing paths with a given injury."

It’s obvious that Stu (successfully) went to a lot of effort to make himself as marketable to a big league club as he obviously could, and in answering that question, also provides some examples other potential job seekers can do to put themselves in a better position to get a job. In the end however, baseball (like many like many businesses) remains an industry based on establishing and keeping relationships. Yes, the analytic/programming/scouting/marketing/facility management skills are required (depending on what your interests are), but more importantly, as Stu recommends, you need to find your niche and get your name out there. As Stu notes when providing his advice to potential job seekers:

“Be passionate about the game, because if you're not, the hours will eat you alive. Have a portfolio of baseball-specific work, be it your own scouting reports, code for your self-made projection system, whatever it is, have something tangible and know it backwards and forwards. Have a specialty or a feel for one -- if you're an Econ major and love that side of things, understand the CBA or how arbitration works. If you're a medical person, write about particular conditions/injuries and apply it to on-field performance. Understand why you will be an asset to a team. Having a firm base in evaluation is helpful, as is having some knowledge of the minor leagues for a given team. Know where the full season teams play so you can speak thoughtfully on some of their Top 10-20 guys and how their level/park can affect their numbers. And last but not least -- NETWORK. Make friends, share notes, share email addresses, share info about what team has an opening where. Get on Linkedin, reach out to people who share the same interests as you and definitely be a part of Baseball Industry Network.”

So to all the job seekers hoping that a trip to the winter meetings will put them on the path to their dream job, don’t get discouraged if you left without an offer. But don’t expect that a productive trip to the winter meetings alone will put you in a good position to get one. Going after your dream job takes a lot of time and effort no matter what industry you aspire to work in. And if that dream job is in baseball, it takes even more time and effort to make it a full time gig. Hopefully some (or even one) of those job seekers see this and so they can put Stu’s advice to good use. So good luck to the people I had the pleasure of speaking to at the winter meetings and to all the other job seekers out there. If I somehow am fortunate enough to speak with any of you again, I hope that by that time you have since become another winter meetings success story.

Thank you to Stuart Wallace and the job seekers at the winter meetings for taking some time out of their schedule to talk to me for this article.