Olivia Oshry: How I Turned My Twenty-Year-Old Self’s Hobby Into A Career
“I honestly couldn’t believe that what I did in my personal time could be a job and that companies needed advice on.”
Olivia Oshry is a seasoned marketing and communications executive with over twelve years of experience at both large corporations and startups. She currently works with brands across industries on brand development, marketing, and PR strategies to turn ideas into impact.
Having started her career leading B2B social media strategy and partnership marketing at AOL, Olivia went on to be a founding member and the first marketing hire at Flowcode, a customer engagement platform that helps brands and consumers directly connect from the offline world to the online world through next-generation QR technology.
While she calls herself influencer adjacent, as her sisters collectively have millions of followers, Olivia has amassed over one hundred thousand followers on social media, partners with brands on influencer campaigns, and helps them with their larger influencer programs.
The Continuum sat down with Olivia recently to talk about her career and her unique perspective on influencer marketing.
You grew up in New York City and went to NYU. You really took advantage of the opportunities that being in the city during college gave you. Can you explain?
When you go to a big city school like NYU, it is natural to have a lot of internships. I think I had seven while I was an undergraduate. I did everything, from working at the Museum of Jewish Heritage to working at AOL when it had just spun off from Time Warner. I had thought I wanted to go to law school, but my internships—especially the one at AOL—really helped me figure out what I wanted to do.
I was working on digital media and social media strategy, and I honestly couldn’t believe that what I did in my personal time could be a job and that companies needed advice on it. I loved being in media and technology and knew I’d found my place. I maneuvered everything that I possibly could to get them to hire me full-time after I graduated.
This was around the time Instagram launched, and Tumblr got acquired by Yahoo. Social media as a tool for brands was a new concept. AOL had a great company culture and a lot of consumer brands as part of its portfolio. I worked B2B corporate social media strategy and then moved over to events. We did events on a big scale like CES, South by Southwest, Advertising Week, and Cannes Lions.
I wound up managing all of these relationships with industry partners, trade associations and thought leaders. I programmed hundreds of speaking opportunities for different executives from all around the world. I was in my twenties, and I was traveling Sunday through Thursday and coming home for the weekend to see my family. It was great.
You were on the team that tried to unify AOL and Yahoo after both were acquired by Verizon. How did you get tapped for such a high-profile project so early in your career? What advice do you have for others who are starting out?
Because of my deep social media knowledge and how that would impact integration, I became part of the team that was working on the branding element of the AOL and Yahoo integration. This was on top of my regular job, which ties into the advice I give—always get involved, always say yes. If there is a brainstorm or any other opportunity to lend your voice or be helpful, do it!
I started my career as an intern. I got there early, stayed late, and took on whatever projects people offered. While it wasn’t customary for interns at AOL to get coffee or order cars for executives, I jumped at those opportunities to be helpful because I think the more times you can say yes, the more people will remember that and tap you for future opportunities down the line.
I still have this mindset. I never say no to anyone, whether that’s someone who wants to meet for a coffee or pick my brain, because I don't think anything good comes from saying no, and something positive could come from saying yes.
You and your sisters were really part of the early days of social media influencers. What was it like then, and how do you think it’s changed?
It’s funny; when I graduated from college, people started to get jobs managing Facebook pages for brands. On the one hand, it didn’t seem like a real job, but on the other, it's one of the most important jobs that somebody can have because a brand’s social media strategy is often its first point of contact with consumers.
I was working on social media for brands, but my sister Claudia—who is a few years younger and was still in college—was really at the forefront of being a social media influencer. She was very good at leveraging the different platforms early on, and by the time she graduated college, she had a good-sized Instagram following. That gave her the opportunity to go to events and work with brands. When she graduated, she didn’t feel like she could get a full-time job because of all of these things she was doing. It was kind of blasphemous at the time—to finish college and not try to get a “real” job—but she’s turned it into a fabulous career.
It is kind of unbelievable how the influencer world has shifted, but I think this economy is still in its infancy stage. Influencer marketing really started as an awareness medium for brands. They would find an influencer and ask them to post about their brand or product. It was a reach game,and brands were focused on influencers with a lot of followers but not on the nuance of who those followers were.
I think we’ve since realized that influencer marketing can be an incredible performance channel. You’ll still get that awareness perspective of someone talking about your brand and loving it, but you can also measure and track whether it’s driving traffic to your site and your own social pages and, ultimately, whether it’s driving sales. Influencer marketing is obviously still paid, but this feels like a more organic way to amplify your brand.
“I never say no to anyone, whether that’s someone who wants to meet for a coffee or pick my brain, because I don't think anything good comes from saying no, and something positive could come from saying yes.”
You mentioned the creator community. Do you think there’s a difference between content creators and influencers?
Good question. In theory, they are the same thing. I think that creator is a more elevated way to say influencer, which recognizes that these people do more than just post pictures of themselves with your product and that it takes skills. They know how to use Photoshop, how to edit videos, and really how to market products. In other settings, brands would have to hire three or four people who together had this skill set.
Creators also have to be multi-platform and know how to make content for Instagram, YouTube, or TikTok, which all require different formats. And they have to make content constantly. To engage their audience, they have to put things up every day and sometimes multiple pieces in a day. I don’t think people know how much work goes into this, and from my point of view, it makes you a founder and a business owner. Influencer may have been the right term for the early days, but I don’t think it fully captures the scope of what they do.
What's the best way right now for brands to work with creators?
Brands should really seek out influencers and creators across the spectrum who actually use their products. You can often see products in the background of other content, and I think every brand manager or social media manager should be diligent about trying to find their products in other people's content, whether that person has 2K followers or 2M followers. As long as they understand the brand’s customers and have a modicum of influence, they could be a good partner.
As a brand manager, if you find a creator that aligns with who your brand is or who you want it to be, I think the next step is giving them your product and letting them use it for a few months instead of just handing them a check and jumping into a relationship. Let them become a fan. There should be a minimum one-month engagement period. Give the creator access to the product, let them live with it, experiment with it, and figure out if it really is right for them. If it is, you can do a larger-scale brand deal. Not only will this be more authentic to the audience, but the creator will do a ten times better job talking about your product because they’ve actually had experience with it.
What about celebrity influencers? Are they still an important component of a brand’s social media strategy?
If a brand has a big budget to bring on a celebrity and it makes sense, that's awesome. But look at the data; a lot of celebrity endorsements don't convert; they don't hit. I come from the mindset of quality over quantity. If you have somebody with 2K followers and 1K of them buy, you’re better off than if you have someone with 2M followers who only converts one hundred of them. In the end, you're spending less and getting a more engaged audience.
There’s room for both, of course, but a lot of times, brands thinking about celebrity influencers want to go big and fast. I think it’s better to start smaller and be really thoughtful about audience demographics and engagement rates.
“As a brand manager, if you find a creator that aligns with who your brand is or who you want it to be, I think the next step is giving them your product and letting them use it for a few months instead of just handing them a check and jumping into a relationship. Let them become a fan.”
You have a pretty sizable following on Instagram. Do you consider yourself an influencer/content creator? What is your content about?
I’ve always considered myself influencer adjacent because it’s really my sisters who made careers out of it, and they are amazing at what they do. I definitely wasn’t doing all that much with my social when I was at Flowcode because I had a full-time job and two kids. I had no time and was also sensitive to how it would look if I posted in the middle of the day. I don’t think a lot of people realize that it takes a long time to make content, and posting something at noon doesn’t mean I made it during the workday.
That being said, now that I have started to work with brands and more openly share my life as a working mom, it's been so fulfilling to connect with my community and share brands that I love and use in my everyday life. I'm really appreciative of the brands that allow me to be their steward and ambassador, and I take that responsibility very seriously.
It can seem trivial to share what I'm making for dinner, or what I pack my daughter for lunch, or what toys my son is playing with, but I love when people tell me that they cooked one of my recipes for dinner, or that their child loves the toy I recommended. We all have a lot on our physical and mental to-do lists, and I appreciate it when I'm scrolling on social and am introduced to a new brand or learn a new mom hack. Why wouldn't I contribute to that ecosystem and share my favorites?
Do you have advice for anyone who wants to be a content creator/influencer? Is it still possible to break into this field now that it’s so crowded?
I definitely don’t think that it's too late, but I also think people don't realize what a hard job it is. You see a lot of people—including celebrities—start podcasts these days and then not follow through because you have to have something to talk about every week, and you have to create and shape that content. If you want to be an Instagram or TikTok influencer, you have to grind out content every single day. Whatever your niche is, you have to be in front of the camera,making stuff every single day. And you have to read all the comments—even the negative ones—and respond to followers and update your website. In a lot of ways, it's harder than a corporate nine-to-five job because you’re always on.
This isn’t me saying not to do it by any means. It’s just me suggesting you have to be all in and love what you’re making content about.
November 28, 2023
