Anya is a global eCommerce marketing and product management leader. Her experience includes working for Facebook as Product Lead, Connected eCommerce and Head of Marketing, Wi-Fi Tech and Innovation, as well as leadership positions at eBay, Target and McDonald's tech headquarters in Silicon Valley. Her portfolio includes building and launching Facebook/Instagram Shopping in 2019. Her previous teams included 50+ app product managers, UX/UI designers, software and data engineers, marketers, analysts/data scientists and monetization/ad tech managers.

She is currently the Adjunct Lecturer of Marketing and Product Management in Northwestern University, Founder and CEO of Taelor, an artificial intelligence-powered clothing rental startup in Silicon Valley, and the Mentor and Entrepreneur-In-Residence of 500 Startups, which is a top accelerator in the world. She is also the author of a best-selling career book, a TEDx Talk speaker, and a social media influencer with 40k followers.

Anya was named in a Girls in Tech 40 Under 40 list in 2018 and nominated as a Marketer of the Year by Min Magazine U.S. in 2013. She and her portfolio are also the winner of 20+ awards including Webby Award Best Shopping App, The Communicator Award, Rising Star Award of Social Network Category by Mobile Village, as well as Honorable Mention of Integrated Marketing Award by Min Magazine.

Q: What's your background, and what are you working on?

I have 15 years of experience leading digital innovation teams at Facebook, eBay, Target, McDonald’s and Sears before launching Taelor. Taelor helps busy men to look good without the commitment of buying clothes, as a menswear rental subscription service.  

Prior to starting Taelor, I held leadership positions at tech and retail companies building their eCommerce business — at Facebook, I led its social commerce business as part of Facebook Shopping; at eBay, I led its app and website for emerging market and business; at McDonald’s and Target, I built its Silicon Valley tech office, where we developed McDonald’s food delivery eCommerce and Target’s iPad app from scratch. During that time, I realized that consumers have changed — they want to enjoy things without ownership, and they support sustainability. I also learned that clothing brands need a new business model to acquire customers as retailers are no longer an effective channel.

I noticed a segment of consumers are under-served. Hunter is an example of one of Taelor’s customer. He is aspirational and out to impress but he’s not into chasing after clothes. Hunter represents a sixty billion dollar market and is growing at 18% annually. Hunter has considered some clothing subscription boxes, but he doesn’t like the commitment of buying stuff from each box.

That’s where Taelor comes in. Taelor is a revolutionary new way for men to rent clothes, allowing them to look and feel great every day while also reducing their carbon footprint. The service uses a combination of Artificial Intelligence and personal stylists to select clothes for men based on their sizes and personal preferences. For a flat monthly fee, you get four pieces of clothes sent to you every two weeks. You can either return the clothes after wearing, or purchase for up to 70% off the regular retail price. Customers then provide feedback for the clothes they wore and receive another box of clothes. No more shopping. No laundry hassles. 10% of the cost, 10 times the value.

As a Taiwanese American immigrant, outside of my corporate executive roles, in the past ten years, I also have been a volunteer career coach with 70k followers. I started Taelor to help more people achieve their goals, starting by dressing as who they want to be. I also fulfill this role as a Lecturer at Northwestern University and 500 Startups, a leading accelerator in Silicon Valley.

Anya Cheng

Q: What motivated you to get started with Taelor?

Over the last five years, I became a power user of women's clothing rental subscription services. Buying clothes became a task of the past.

While I spent years working for my American dream and became a successful leader at Facebook, eBay and Target in Silicon Valley, many days, I actually didn’t feel ready for my day. However, rental subscriptions changed my life — on the one hand, I don’t need to spend time to think about what to wear; on the other hand, I know I will look “put together” for any occasion, no matter if it’s a job interview, giving a TEDx Talk, going on vacation, or just one of those farmer’s market days. Rental subscription services gave me peace of mind, and I felt confident and ready to take on the day.

Over the past ten years, outside of my corporate career, I have been volunteering as a life coach. I have mentored hundreds of people who are all looking to achieve their own personal goals, and I’ve realized that I am not the only one who is looking to become a better version of myself. Through mentoring, I’ve learned that feeling confident is essential to achieving success. And, usually, all people need to feel confident is a little help.

That’s where the idea of Taelor came from — to help busy professionals feel more confident by helping them dress stylishly without having to worry about their clothes.

Take my friend Guan, for example. He is an honest, nice and successful engineer in Silicon Valley. Guan is a true gentleman, but he has been single for years. He is looking for true love, and he deserves it. My friends and I knew that Guan’s problem wasn’t his personality. It was his wardrobe. He dresses like a nerd — and not in a good way.

One time, a group of us took him shopping and gave him a makeover. He not only looked totally different but he felt more confident. However, it didn’t last — after a few months, he went back to his old style.  

I realized that a service like Taelor could really help tons of great men, like Guan, or women who wear menswear to reach their potential.

I teamed up with a group of Silicon Valley executives — from operational experts behind Amazon Go, Starbucks and Singapore Airlines, artificial intelligence patent-owners from Google, Facebook and eBay, fashion designers from clothing rental subscription companies, and male audience marketers from Audi and Volkswagen.

We named the company Taelor, which phonetically references the occupation “tailor” and is also a common name. It describes the person who adapts clothes to fit with a particular person's body and style.

We believe Taelor is just like you and me — normal, everyday people who have a dream. Taelor is a service to help people achieve their goals. A story of the American dream. A company born because of friendship.

Q: How have you attracted clients and grown your platform?

We just launched our pilot, and current users found us through Facebook groups and through word of mouth from their friends who heard of us on Facebook, Clubhouse events and Linkedin.

To distribute our service, the right marketing messages and channels are key. We have been working on both consumer marketing and partner marketing.

On the consumer marketing side, we are using two key messages: “look good” and “effortless fit”. The “look good” message is supported by the fact that consumers get utility benefits, such as styling service and wearing a variety of clothes. For “effortless fit”, consumers save time without shopping or doing laundry.

We are incorporating our strong value propositions into our marketing messages. People sign up for a combination of reasons: having a personal stylist, wearing a variety of clothes, including styles outside of their comfort zone. In addition, compared to the cost of buying those clothes, for less than 10% of cost, they can wear 10x more clothes. Some customers also love the fact that they don’t need to do laundry or ironing anymore, which allows them to have more time to do whatever they love.

We are also leveraging marketing messages about “dress up to go out.” With COVID-19 vaccines, more customers are ready to go back to the office and go out for fun. Many of them said that they would like to impress their friends and coworkers when they are going out.

From our research and pilot that was just launched, we know that our target audience is not into fashion. Therefore, for marketing channels, we are using PR, engaging with the communities and partnering with non-fashion influencers to drive awareness and consideration of Taelor for free. Once consumers have exposure to our service, we are leveraging paid advertisements to retarget them and convert them to be our paid subscribers.

On the partner marketing side, we are co-marketing with clothing companies, building employee benefit programs and working with dating sites.

As a marketing faculty member at Northwestern University, a social media influencer with 70k followers, and former Head of Marketing at Facebook’s Tech and Innovation team, I am confident that after testing and iterations, we can find effective and efficient ways to grow Taelor.  

Taelor box

Q: What are your goals for the future?

We plan to build up scalable tech and operations, test and find effective and efficient customer acquisition playbooks and secure brand more partnerships.

We are running a paid pilot and will continue to gather customer feedback to help us improve on user experience and engagement. We will also set up a scalable operating model and secure brand partnerships to expand assortments. Lastly, we will reach over significant data points from customers, clothing assortments and feedback that will help us build and enhance the AI algorithms.

Q: What are the biggest challenges you've faced so far?

From time to time, we heard potential investors saying that they think men don’t care about looking good and would only want to own everything. However, from industry reports, my experience at Facebook, eBay and Target, and from our initial pilot, we believe that rental subscription will catch on with men. There are men who want to look good to achieve goals and men who support sharing economy and sustainability by renting clothes.

This is especially true for men who don’t actually care about fashion, because they likely want to outsource the styling, shopping and laundry work to Taelor. To overcome the doubt about the potential of menswear rental services, we have been researching and testing hypotheses during our pilot.

The insights from our research, which we conducted with a former Nordstrom researcher, and our initial customer feedback has shown that men are looking for convenience and the ability to save mental energy. They like effortless fits and the fact that they have more time for whatever they are into with our styling service. They love the fact that there is no pressure and commitment for them to purchase items, even though from our initial pilot, our customers mostly end up loving items and purchasing them.

In addition, men are also more practical and care about value, which they get with Taelor by spending $60 to wear up to $1,600 worth of clothes every month, or the time and money they can save without shopping or doing dry cleaning anymore. They also look for high quality, performance items and are willing to buy after renting them. This is different from female rental subscription, which is primarily focused on the number of assortments.

According to Euromonitor International Limited, the menswear market is 30% of the total apparel market. Compared to the industry average of 2% growth rate, the Circular Fashion market, which is made up of mainly resale and rental, is the growth driver with 10-18% Growth Rate. That is 21 times faster than retail. It’s expected to grow to a $66 billion market by 2025. Resale is booming with companies going IPO, and rental services have just started.

The menswear market is under-served. Currently companies only offer subscription boxes for apparel purchase or high-end fashion streetwear rental, while Taelor is focused on offering rental subscriptions for everyday menswear. Renting has come a long way from the tuxedo prom shop, and I believe that a rental subscription for everyday menswear is filling a gap in the marketplace. We will continue to test, learn and optimize the business.

Anya Cheng

What's your advice for female founders who are just starting out?

“You are better than you think.”

I recently participated in an entrepreneurship competition. Before the competition, I found former judges and practiced the pitch over 42 times. Yes, 42 times. In addition to practicing the pitch, I also improved operations, business models, pricing and technology of Taelor based on their feedback. But, I lost the competition. Here was why I lost it —

The competition format was a pitch followed by a Q&A. To prepare for the Q&A, I listed every possible question and put the answers in the appendix — there were no questions that I couldn’t answer.

On the day of the competition during the Q&A, I wanted to show that I had prepared the answer — when I got the question, I looked through slides and tried to show them my preparation. I didn’t “connect” with the judges. Using a metaphor for you to better understand the situation — it’s like in an open-book exam, I was trying to find answers in the book, instead of just spending time to think about the questions and writing down the answers, which I know very well.

I should have been present, shared what I know very well, had a discussion with judges, and showcased my charm and passion.

In hindsight, I forgot that I was a Fortune 500 company executive with 15 years of experience. All I thought of at the time was that I am a new founder, and I had to prove myself.

If I would have believed in myself and remembered that “I know my stuff!” I could have won the competition. I know that I didn’t lose — I learned. Therefore, I want to share the learning experience with you, and remind you and myself that “You are better than you think!”