Interview With Jackie Oshry

Interview and article by Sarah Kurland, ’18

Jackie Oshry, AKA ‘JackieOProblems’

BeFunky Collage 

Many of us are familiar with Jackie Oshry, a Colgate alumnus who runs a successful Instagram account called ‘JackieOProblems’. Oshry is a media strategist at AOL, a global digital media and technology company. As an alumnus who has succeeded in breaking into the marketing and advertising industry in the competitive New York City job market, she’s an incredible source of knowledge and advice for Colgate women looking to enter the business field. Oshry answered some questions for Colgate Women in Business members and readers about her success strategies and her transition from Colgate into the NYC workplace.


  1. As a successful graduate from Colgate, what were you involved in on campus that helped you make the transition into working in New York?

Oshry: I didn’t know that I wanted to work in media until I was a sophomore at Colgate. You’d think that once I had this realization I’d regret being at a school without a communications program, but that wasn’t the case. At Colgate I was able to receive a well-rounded liberal arts education, and in order to supplement my desire for media experience, I worked tirelessly on my own social media presence during my years as a student. By my senior year, I had gained a pretty big following and was able to secure a job in the Media Communications Office as a social media intern. There, I was able to gain real world experience that I could then reference when applying for jobs.


  1. What was the hardest part about your job/internship hunt? What advice would you give to Colgate women in the same position now?

Oshry: The hardest part about the job/internship hunt is that for every entry-level job and internship, you’re expected to have year’s worth of experience! But when you’re applying for your first job out of college, or even your first internship, when do employers think you had the time to gain this experience? I saw the funniest meme that totally sums up this sentiment:

Also, it’s easy to apply to a ton of jobs but it’s a lot more difficult to make sure your application and resume are seen. Job sites and LinkedIn postings are great, but you’re applying along with thousands of other candidates. That’s why I would periodically apply for positions I was seriously interested in, just in case they missed my application the first time (or second and third times).


  1. What’s the best part about your job?

Oshry: The best part of my job right now is getting to work with my family. Two of my sisters also work for AOL, and we actually end up working together on projects often! My third sister is a student at NYU, which is right down the street, so the four of us are able to meet up during or after work and bounce ideas off each other. It’s a really unique and special situation that we’re in, and I definitely don’t take it for granted!


  1. You and your sisters are well known on social media. What would you advice Colgate women about branding themselves?

Oshry: In this day and age, branding yourself is everything. Even if you don’t consider yourself a social media person, if you have a Facebook page, a Twitter profile, or an Instagram account (which you obviously do) you have a brand. It’s important how you portray yourself on these platforms, because that’s the first place people go when they want to see what you’re about (whether it’s for professional reasons or stalking purposes).


  1. How would you define success?

Oshry: Success means a lot of different things to me, but if I had to sum it up I’d describe it as meaningful work that makes you happy and allows you to buy those shoes you’ve been eyeing.


  1. What are some major goals of yours?

Oshry: Some of my major goals include becoming important enough for Colgate to name a building after me. Or a stadium, I’m not picky.


  1. Can you talk a little about your transition from Colgate to the workplace?

Oshry: For me, the transition from Colgate to the workplace was really natural. I don’t think students realize just how much work you do at Colgate and the time management skills you gain over the course of four years. Once I graduated, I was so used to the Colgate workload and the pace of things that the real world actually turned out to be relatively slow. In the real world you don’t write a 20-page paper in the span of 3 days just so a Professor can grade it and then it can sit in your parents basement for years to come. The work you do once you graduate serves a purpose for the company you work for and you can actually make a difference, which I think is pretty cool!


To get to know more about Jackie and her life at AOL, follow her on Twitter/ Instagram/ Facebook/ Snapchat/ Everything Else at @JackieOProblems




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