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Inspirational Women Leaders Of Tech: Julia O’Mara of Pickle Poll On The Five Things You Need To Know In Order To Create A Very Successful Tech Company

An Interview With Candice Georgiadis

As a part of my series about “Lessons From Inspirational Women Leaders in Tech”, I had the pleasure of interviewing Julia O’Mara.

Julia O’Mara is the Co-Founder and Head of Growth of Pickle — a social commerce platform that combines the efficiency of online shopping with the social benefits of in-person shopping. She previously worked as a product manager at Blackstone, where she focused on creating data analytics and data visualization solutions for the fundraising teams. Prior to Blackstone, she studied Materials Science Engineering as well as Entrepreneurship at the University of Pennsylvania.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

After graduating from Penn in May 2019, I moved right to New York City and started as an analyst at Blackstone. The beginning of my job was great, and I learned a ton from my team and peers. Unfortunately, the pandemic started after only 9 months into my time in the city, so I went back to Maryland to stay with my parents. Working from home was quite an adjustment and I definitely missed working with my colleagues in real life. Brian, my Blackstone co-worker at the time, told me a little bit about an idea (Pickle) he was working on and I was immediately interested. I started out helping with the design and a bit of the brainstorming, but before I knew it, I became heavily involved with the company. I always thought I might get into the startup world one day because of how much I enjoyed my Entrepreneurship classes at Penn. I realized this was an incredible opportunity to make the startup jump, so in the spring of 2020, I left Blackstone and started working on Pickle as a full time co-founder.

Can you share the most interesting story that happened to you since you began at your company?

An interesting story that has happened to me since starting at Pickle was navigating one of my busiest days where I was wearing quite a few hats. We had just onboarded our summer interns and I had been working on my management experience. I was looking at my calendar and saw an absolutely booked day the next week. I remember getting a bit nervous about how packed it was going to be and if I would be able to manage it. This packed day finally came and I jumped into it. I started off the day doing some research on the social commerce market, moved onto rolling out a few influencer campaigns, negotiated a new influencer partner contracts, conducted several user interviews, strategized some new features and enhancements with Brian, put together some marketing collateral and social media plans, filmed two TikToks, and then wrapped up the day with a presentation to a college entrepreneurship club. That was the day I remember realizing this is exactly what I want to do. Although it’s challenging to be a founder, it is incredibly rewarding and exciting to be such an integral part of a company. I look back at this day and think it’s funny that I was a bit nervous to accomplish it because this is how the majority of my days look now.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

One funny mistake I made pretty early into my time at Pickle was a classic “work from home” mistake. I had just finished some independent morning work and then had a call with our user acquisition and marketing team. This was an internal meeting, so naturally I was wearing an old college sweatshirt and a messy bun. When trying to join the Zoom meeting, I accidentally clicked on Brian’s personal meeting room link instead of my own (we used his so often it was saved in my notes). I then entered the middle of an intro investor call looking incredibly casual and confused. The investor was super nice about it and Brian used it as a good time to introduce his co-founder. I’m not really sure if the lesson learned is to either always look nice on Zoom or to always use the calendar invite instead of a saved Zoom link (probably the latter).

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Adjusting from a corporate America job to building a business with a very small team was difficult but exciting. The beginning was challenging because I didn’t know what I didn’t know. However, it’s pretty amazing to see everything I’m doing has direct value-add to the company and our goals. The level of responsibility I gained overnight was definitely overwhelming at first. I remember thinking that there was so much to do, but the best way to approach it was just picking a place to start and going for it.

Fortunately, I have a great co-founder to work through those challenges and learning experiences with. I never considered giving up on Pickle — I knew starting a company would be hard, but I think some of the hardest things in life are the most memorable and worthwhile. My drive and perseverance through challenges definitely came from my student athlete experience at Penn. Balancing an engineering major and a D1 sport was not easy. However, I pushed forward and learned how to better prioritize my time and ask for help from coaches, peers, and mentors. I have definitely been able to translate those skills from Penn to my work at Pickle.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

John Diaz, my first manager at Blackstone, greatly impacted the beginning of my professional career. He was an awesome first boss — he was always fully transparent, provided truly constructive feedback, and cared about my professional career both at Blackstone and outside of Blackstone. He helped me succeed in my role and pushed me to always strive for excellence. I remember one of our first one-on-one meetings where he told me we could use that time to discuss career development. Even after we stopped working together, we stayed in close touch and he was one of the first people I talked to about making the jump to start Pickle. He was so supportive and encouraged me to take the opportunity to start a company. I couldn’t have asked for a better first boss/mentor — thanks for all of the support and guidance, Diaz!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

You can’t control what happens, but you can control the way you react to what happens. My therapist told me this during one of our sessions over the pandemic. We had been discussing best ways to deal with stress around some personal life events that had been challenging to navigate. As someone who often strives for perfection, it’s difficult when things don’t go as expected. At a startup, priorities are constantly shifting/evolving, and things don’t always go according to plan. Controlling my reaction to bumps in the road and choosing to have a positive attitude has been incredibly helpful for my overall mental health. Instead of dwelling on what went wrong, I focus on my reaction and what I can control. It also helps that I have an awesome co-founder to navigate these challenges with. We love to throw in a bit of humor after something doesn’t go as expected.

We’d love to learn a bit about your company. What is the pain point that your company is helping to address?

To help frame the pain point we are addressing, think about your experience shopping online for a new outfit versus your experience shopping in person for a new outfit. Online shopping is currently very siloed, individualized, and lacks the key feedback loops that help lead us to a confident purchase decision. Some of the most valuable parts of shopping in person involve social interactions with friends and in-store experts. We rely on trusted feedback to make confident purchase decisions. Pickle aims to seamlessly integrate social interactions, feedback loops, and style communities into online shopping. Pickle allows people to gain validation for potential purchase decisions by better connecting users to people of influence, whether that is fashion influencers, trusted personal sources, and/or other Pickle users who share similar style preferences.

What do you think makes your company stand out? Can you share a story?

The name and logo … kidding! Our commerce-focused social graph makes Pickle a unique company because we are building a community that is truly centered around enhancing the online shopping experience. We tackle three essential groups of influence on Pickle. We give our users access to their trusted personal network, their favorite fashion/style influencers, and also larger-scale style communities that consist of people with similar style preferences. Feedback and inspiration from these groups of people allow users to feel confident in their purchase decisions and experience the valuable social interactions that occur within in-person shopping.

Are you working on any exciting new projects now? How do you think that will help people?

Yes! We’re currently building out a Discover page that better connects our users to other users with similar style preferences. This includes highlighting verified fashion influencers and their curated communities. These communities consist of users who love an influencer’s style and therefore share similar style preferences and fashion taste. One of the main benefits of these groups is that users can give and receive feedback at scale with other Pickle members who have relevant opinions. For example, if a user is looking to buy a dress for a formal event, they are able to get inspiration from an influencer’s community and also ask for their feedback around a few dress options. Access to these opinions is incredibly helpful to make confident purchase decisions and increase overall confidence when wearing that purchased item.

Are you currently satisfied with the status quo regarding women in Tech? What specific changes do you think are needed to change the status quo?

I don’t think I’ll be satisfied with the status quo regarding “women in Tech” until there doesn’t need to be that designation. There are incredible groups and programs for women in tech because we’re such a minority. In the future, I hope this designation won’t be as necessary because the field will be more equally distributed among both men and women. Changes need to start with early education around the tech field. Gender stereotypes around certain jobs and careers should be removed and both boys and girls should be equally educated about the industry.

In your opinion, what are the biggest challenges faced by women in Tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

One of the first challenges that comes to mind is the assumption that the men are in charge in the room (or virtual room). This assumption definitely puts a woman in a more challenging spot when starting or leading a meeting. My recommendation is to immediately start/lead the small talk before diving into the meeting — this will help set the tone that you’re going to be leading the meeting.

Another challenge is walking the line of how assertive to be. Women can be perceived as rude if they are too assertive, but also perceived as a push-over if they aren’t assertive enough. Men don’t typically deal with this challenge and can be as assertive as they want. My recommendation here is to lean on the side of being more assertive than passive and pay close attention to the room as you are speaking. The real-time reactions and body language can help you navigate the best way to interact with your colleagues.

Finally, since women are a minority in tech, they are often in male-dominated conversations that might be around topics they aren’t as familiar with. To give a personal example, when I was at Blackstone people in the office would often talk about football games from the weekend. Regardless of gender, I always want to be educated and contribute to a conversation, so I started every Monday morning running on the treadmill in front of a TV that showed all of the game highlights from the weekend. I was then able to contribute more in these conversations and enjoyed getting more knowledgeable about the season. I think leaning into some of these topics so you can connect better with colleagues is important regardless of who (men or women) are dominating the conversation.

What would you advise to another tech leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth or sales and “restart their engines”?

From my experience, my general advice about boosting growth or sales is to do a thorough data analysis to try to determine the reason behind the slowing growth and then conduct hands-on interviews or surveys with the users or customers. Be sure to talk to the people who are actually using your product or service. At Pickle, we make a lot of predictions when rolling out new features and then we monitor those features and continuously learn from our users. We then work to improve upon those features and ensure they are addressing our users’ largest pain points.

In your specific industry what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

Partnering with passionate fashion or style creators has been very successful to onboard new users to Pickle. These influencers already have established social media platforms with loyal followers who truly enjoy their fashion and style recommendations. Pickle helps creators closely interact with their audience within a community setting that allows them to give and receive feedback around fashion. Our influencer partners have had a lot of success inviting their followers to join Pickle. Their followers (aka our new users) are able to use Pickle to engage with these creators at a deeper level in the fashion space. They can get product recommendations, feedback around purchase decisions, and outfit combinations from their favorite influencers and the entire style community.

Based on your experience, can you share 3 or 4 strategies to give your customers the best possible user experience and customer service?

1. Keep the platform simple and easy to navigate to ensure most pieces of functionality are easy to self-discover. We try to keep Pickle very user friendly so users can easily understand the app without getting a full demo.
2. Frame features within use cases instead of pure product functionality. Our users are able to better understand features such as Pickle Jars and Style Communities when they understand the real-world application of using them as well as the value they get out of those features.
3. Listen to your users/customers when they provide feedback or ask repeated questions. For example, after some interviews, we heard that users found the in-chat functionality helpful, but were navigating back and forth between that and another feature in the app. We then rolled out a seamless integration to make it easier for the chat feature to be accessed in relation to another feature.

As you likely know, this HBR article demonstrates that studies have shown that retaining customers can be far more lucrative than finding new ones. Do you use any specific initiatives to limit customer attrition or customer churn?Can you share some of your advice from your experience about how to limit customer churn?

For our user retention strategies, we focus heavily on making sure our users are connected to influential sources to improve their shopping experience. After activating our users (i.e. making sure they interact closely with some of our features), we focus on their network within Pickle. When they are able to easily access their close personal network, their favorite style influencers, and an entire community of people with similar style preferences, they are much more likely to return to Pickle to continue interacting with other Pickle members. As far as advice to limit churn — analyze usage data to determine exactly what gets a user beyond the activated stage and into the retained stage and be sure to bring forward and emphasize that functionality or value-add.

Here is the main question of our discussion. Based on your experience and success, what are the five most important things one should know in order to create a very successful tech company? Please share a story or an example for each.

1. A strong founding team is everything.
Brian and I had a great working relationship at Blackstone, but we were also good friends. This friendship led to a strong founding partnership, which has been essential to our growth and success so far at Pickle. We’ve navigated incredibly important company decisions together as a team. We also have a good amount in common, including that we were both collegiate athletes. Brian played football at the University of Maryland and I played lacrosse at the University of Pennsylvania. We both have the student athlete tireless work ethic and drive to be excellent. These traits allow us to fully trust each other and get our jobs done effectively and successfully.

2. You need to be passionate about the problem you’re solving.
The reason I was able to leave my stable job at Blackstone is because I fully believed in the idea behind Pickle and the problem that we’re solving. You will only be able to work as hard as you are passionate about something and since starting a company requires a tremendous amount of commitment and time, you need all the passion you can get. Fortunately, I am able to wake up to a packed calendar or a long day ahead excited because each day we are building and improving upon the best possible solution for our users.

3. Use data to make decisions.
Data is important for almost all decisions with a company — one example of how we’ve leveraged data effectively is throughout our influencer partnerships. We are able to launch partnerships and measure their success with data in order to determine the best ways to engage their new communities on Pickle and also ensure we are getting the most value out of the partnership.

4. Listen to your users/customers.
Our users are key to the success of our company. We use Google Analytics to better understand how they are using Pickle and we conduct consistent user interviews to see how we can improve the platform and what new features should be prioritized.

5. Test your ideas and use MVPs.
Before making a big decision to roll out a new feature or change strategies, test it at a smaller level. We have a beta group within Pickle that has access to new features before we release them to the entire Pickle population. These users are key to help us measure the value of potential new features. Once we have confidence in a feature, we work as fast as we can to get it fully implemented.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I would love to inspire a large mental health movement that de-stigmatizes the conversations around mental health starting at a very young age. I don’t think I knew much about this area until college and wish I had learned about it earlier. It would be great to start these conversations and educational classes as early as middle school. Normalizing conversations about mental health will reduce the stigma around asking for help and utilizing resources such as therapy. If we can build a strong foundation around prioritizing mental health and having access to mental health resources, this will have a huge impact on the generations to come.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them :-)

I would love to have a private meal with Sara Blakely, the CEO of Spanx. I find her story inspiring and I love the way she gave back to her entire company after selling her majority stake in the company. I’d love to learn more about how she navigated scaling her business and what her most valuable lessons learned are as a female CEO.

Thank you for sharing your insights and predictions. We appreciate the gift of your time and wish you continued success and good health.



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Candice Georgiadis

Candice Georgiadis is an active mother of three as well as a designer, founder, social media expert, and philanthropist.