Gap’s Youngest Director Ever Talks Her Nontraditional Career Path and How It Led Her to Her Dream Job

by Giuliana Carranza

Gap

October 2, 2019

In a startup-esque space on the Lower East Side of Manhattan, we come face to face with Rachel Tipograph, a Gap Inc. veteran that humbly sports several fancy titles: the youngest ever Director at Gap, a 2014 Forbes’ 30 under 30 recipient, and CEO of MikMak (an eCommerce platform for social video and beyond that allows brands to capture valuable retailer data, improve media channel performance and build qualified shopper audiences).

Don’t let the high accolades fool you, Rachel’s the epitome of a down-to-earth CEO. She rolls into the office at a prompt 9am, wearing all black, sneakers, and a backwards MikMak ball cap. We sit down and get to right to business, asking the nitty-gritty of how she became a 24-year-old Director at Gap and how this experience led her to launch her dream company.

You became a Director at Gap at 24 years old! How did that happen?
I’m a native New Yorker (technically Northern Jersey, so people from Manhattan don’t love it when I say that) and my family has always been in retail, so it’s in my blood. I studied entertainment business at NYU; though, I never learned from a classroom, I’ve always been a person who loves to work. At the time, blogging was the latest thing to hit the internet, and it became very clear to me that the world of content was about to change, becoming democratized and commoditized. I have a theory that whatever happens in media will come to commerce because they share a similar relationship with the customer. Through my time at NYU, I built my first company, called TIPO Entertainment (my friends call me Tipo). I marketed comedians to college campuses through social media. It was a great deal for them because they’d make $75 in a NYC comedy club, but they could make $10k at say Syracuse University. Unknowingly, through TIPO Entertainment, I was one of the first people to advertise on Facebook.

Then, one of my professors connected me with Time Warner. They were looking for a “young person” to reverse mentor their executives on the internet. At the time, video sites like Hulu and YouTube were becoming popular, so companies like Time Warner were feeling the pressure bubbling up beneath them. I went into the President’s office and spewed my beliefs on Internet and how it would disrupt her company, all while being 20 years old; it was crazy. I wanted to make that my career, but I had no idea what that job title would be (it didn’t exist yet). When I was graduating it was the height of the financial crisis, and the only companies that were hiring were in the internet and social media spaces.

So then you found Gap, or rather, Gap found you?
Yep! I got recruited by an agency, and they had just won some big-name clients, Gap being one of them. Gap was looking for someone who grew up on the Internet to lead their digital and social strategy. At Gap, I’d walk into the CMO’s office with my iPad and tell him what I’d do if I were in his role and what his business strategy should be. Gap gave me an incredibly unique opportunity to build a global digital brand team from the ground up at the age of 24, all while giving me permission to do the work that I knew was instinctually right. I’m so grateful for that. They’d tell me, “ask for forgiveness after the fact” and gave me the resources to make my ideas come to life. We were the first brand on Instagram and Vine. We did a Tumblr takeover that hadn’t been done before, and I built an influencer seeding program from scratch. I always say I received my MBA in retail at Gap because I learned so much from the leaders there.

What inspired you to launch MikMak?
When I left Gap at end of 2014, the venture world was coming to NY from San Francisco. I could see that money was coming to New York, and I saw an opportunity. Truthfully, I always had the soft cushion of Gap to fall back on, so I felt like I had nothing to lose. Gap gave me all the confidence in the world to go out and try something. I knew that even if I failed, I’d known so many people leave Gap and come back, and I could do that, too.

It sounds like you’ve trusted your gut and it’s paid off. Where did that instinct come from?
I pay attention to customer behaviors; wherever attention sits, opportunity lives. Recently, I gave a talk at a conference for women who run independent retail businesses. Many of them had built their business on the backbone of Facebook Live. So for me, there’s an opportunity to go beyond Facebook Live for these retailers. There are pockets of attention on other channels that they could be grabbing. For example, 50% of gamers are middle aged women. These people are spending 12 hours a day live streaming their video games. That’s a captive audience for them to infiltrate on Twitch. I’m always thinking about what behaviors I can introduce that won’t be intrusive to my audience’s everyday workflow. 

Bottom line: you must have faith in your own skills.

What’s the best part about starting your own company?
The best part is the present moment. I have an incredible team of 30 people. To give an example of our culture, I’m really into fitness, and I noticed that other people here are into it too. As the company grows, it’s important to me to make sure people socialize outside of work, so I created a company benefit called MikMak six pack. If you take a class with two or more MikMakers, I pay for it. Every single day there is a group of MikMakers working out together. The team loves each other, and they’re always working out. This spring, Inc Magazine named us one of the best new workplaces to work for. This is my proudest moment. Out of all the accolades I’ve received, the only one I care about, is building a great workplace.

What’s your opinion on the changing retail landscape?
Today, it’s easier than ever to launch a brand. We’re at the highest point of the mountain of direct to consumer brands. The cost per acquiring a customer is only increasing. I’m not bullish on DTC, I’m bullish on marketplaces and wholesalers (Amazon, Walmart, Sephora) helping brands with their ecommerce conversion in those environments. There’s a whole slew of pain points from consumer side that major eRetailers solve for (shipping rates, speed, convenience). Seeing brands like Harry’s razors end up on the shelves at Target. What’s old is now becoming new again.

Looking into your crystal ball, what does the future of retail look like?
For retail, last mile delivery will be huge, fewer and fewer people will go into stores, but they will still be transacting in brick and mortar environments. For example, now grocery shopping is something you can do online. Think about Gen Zers, many of them won’t know what it’s like to step into a grocery store! Culturally, that’s a huge shift. If you think about it, that’s the first in-store experience you remember. So if you never go into a grocery store, why would you go into a physical clothing store? I’m excited to watch that develop.

What’s the best career advice you’ve ever received?
A mentor once asked me, “what risk can you afford to take?” It’s a great question to use to frame your life because once you recognize that some risks won’t backfire in a way you’d imagine, you should take them. That’s how you create progress.

I also believe in our line of work communication is paramount and having confidence in your own voice will take you 80% of the way there. I love to instill confidence in my team’s voice and even encourage people to take an improv class; it’s transformational and helps you think and communicate quickly. It teaches you how to build on a conversation through their "Yes, and..." philosophy. And, possibly most importantly, it teaches you that you can laugh through any failure.

Excuse us while we go sign up for an improv class. We’re so happy to be a part of Rachel’s career journey, and we can’t wait to see what she does next! Interested in joining the Gap team? See jobs here.

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