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• Samantha Shih sold her custom clothing company 9Tailors to join LookSky as chief brand officer.
• Shih founded 9Tailors in 2008, growing it through challenges like the financial crisis and pandemic.
• Her C-suite role both doubled her salary and allowed her to balance her work and family life.

This as-told-to essay is based on a conversation with Samantha Shih, a 43-year-old chief brand officer from Boston. It's been edited for length and clarity.

After graduating from Brown University in 2003, I worked as a consultant at Deloitte for three years before spending a year in China. There, I started making custom clothing, which inspired me to open a custom suiting and shirting company. I founded 9Tailors in Boston in 2008.

Launching a business was challenging because I had little experience in retail and fashion and had to learn everything from scratch. I had some business strategy knowledge from working at Deloitte but didn't have operational knowledge.

I learned and grew the company for 14 years. In 2022, I sold 9Tailors and jumped ship to work for a startup.

Launching a company in 2008 was tough

I had a lot of friends who were getting laid off, but I was optimistic. You can only go up from the bottom, so I thought it was an excellent time to start a business.

The company started online, keeping no inventory and making everything to order. This allowed us to identify our target customer — young professional males looking to dress up for work or weddings.

We've been profitable since year two, winning awards and garnering press until the pandemic threw everything off track. Running a high-touch custom clothing company that needed in-person contact and relationships was stressful. We pivoted toward making masks and sold out immediately.

Around this time, my brother called me one day out of the blue

My brother told me his former boss was advising LookSky — an Asian direct-to-consumer fashion brand looking to enter the US market — and they wanted to speak to a fashion industry expert. I had no set expectations for these calls — I enjoy helping people and sharing industry and fashion insights.

What started as one call turned into three or four calls. I met with the chairman, CEO, and the rest of the C-suite team. The company's chairman asked if I was interested in joining them.

I had to think about it. 9Tailors was never busier after the pandemic; there was so much pent-up demand for suits, shirts, and dressing up, and our revenue kept growing.

Two things made the decision easy for me

LookSky allowed me six months to transition out of my business and design my dream job description from scratch. Although I suggested the position of creative director, they offered to hire me as the chief brand officer. I was pleasantly surprised they wanted me at the C-suite level.

I loved running my own business but wanted to make more impact, so the opportunity arose at the optimal time. At LookSky, I would have the opportunity to scale a personalized experience to potentially millions of users.

Also, I had my first child in 2017 and wanted to spend more time with him instead of working crazy retail hours. I had started feeling worn down.

I accepted their offer and nearly doubled my salary at 9Tailors.

Balancing both jobs for a while was tough

During the six-month transition, I worked about eight hours daily, six days a week on 9Tailors. Then, after my son went to bed, I dedicated time to LookSky, often for team meetings or marketing and branding projects. I thrive on being busy, so it was manageable.

LookSky asked me to sell my business, but I couldn't talk about it until we signed the papers and closed because it could destabilize my clients and team if it didn't go through.

The final sale was to my CMO. Even though several businesses expressed interest in buying, I preferred to sell to someone who knew the company, our clients, and how we operate.

My last day at 9Tailors was the same day I announced my departure and the sale of the business to the team. To help transition, my husband, who worked at the company for a good chunk of the 14 years that I did, stayed on for another six months.

I work remotely for LookSky, as most of my team is in Asia

Working remotely was initially a shock because I'm an extrovert who loves being around people, but one of the biggest advantages is having more control over my schedule.

Mornings and evenings are typically dedicated to team calls. Afternoons provide a window for productive personal time — I might work out, dive into a business book (I'm reading "Good to Great" by James C. Collins), or listen to a startup or tech podcast like Lenny's Podcast, Hard Fork, or How I Built This. Best of all, I can attend my son's events and activities.

Last summer, I was diagnosed with breast cancer, which was a shock

After hearing of my diagnosis, my team could not have been more supportive, telling me to take as much time as needed. I like being busy and productive, and work actually allowed me some reprieve.

I've found a company that nurtures my strengths and encourages and supports me in learning new skills. I'm surrounded by bright people who motivate me to do my best work. I've grown and developed tremendously.

I don't miss running 9Tailors, though I'm incredibly grateful for the experience. While I might consider running another startup in the distant future, I'm genuinely happy with where I've landed.

Have you been poached and want to share your story? Email Lauryn Haas at [email protected].

No ugly Christmas sweaters here

She topped it off with a Santa hat for festive flair

• Depop's new gen-AI feature creates item descriptions based on photos that users upload.
• The tool has boosted the number of listings on the company's website and saves sellers time.
• This article is part of "CXO AI Playbook" — straight talk from business leaders on how they're testing and using AI.

Depop is an online fashion marketplace where users can buy and sell secondhand clothing, accessories, and other products. Founded in 2011, the company is headquartered in London and has 35 million registered users. It was acquired by Etsy, an online marketplace, in 2021.

Situation analysis: What problem was the company trying to solve?

Depop's business model encourages consumers to "participate in the circular economy rather than buying new," Rafe Colburn, its chief product and technology officer, told Business Insider. However, listing items to sell on the website and finding products to buy take time and effort, which he said can be a barrier to using Depop.

"By reducing that effort, we can make resale more accessible to busy people," he said.

To improve user experience, Depop has unveiled several features powered by artificial intelligence and machine learning, including pricing guidance to help sellers list items more quickly and personalized algorithms to help buyers identify trends and receive product recommendations.

In September, Depop launched a description-generation feature using image recognition and generative AI. The tool automatically creates a description for an item once sellers upload a product image to the platform.

"What we've tried to do is make it so that once people have photographed and uploaded their items, very little effort is required to complete their listing," Colburn said. He added that the AI description generator is especially useful for new sellers who aren't as familiar with listing on Depop.

Key staff and stakeholders

The AI description-generation feature was developed in-house by Depop's data science team, which trained large language models to create it. The team worked closely with product managers.

Colburn said that in 2022, the company moved its data science team from the engineering group to the product side of the business, which has enabled Depop to release features more quickly.

AI in action

To use the description generator, sellers upload an image of the item they want to list to the Depop platform and click a "generate description" button. Using image recognition and gen AI, the system generates a product description and populates item-attribute fields on the listing page, including category, subcategory, color, and brand.

The technology incorporates relevant hashtags and colloquial language to appeal to buyers, Colburn said. "We've done a lot of prompt engineering and fine-tuning to make sure that the tone and style of the descriptions that are generated really fit the norms of Depop," he added.

Sellers can use the generated description as is or adjust it. Even if they modify descriptions, sellers still save time compared to starting with "an empty box to work with," Colburn said.

Did it work, and how did leaders know?

Depop has about 180,000 new listings every day. Since rolling out the AI-powered description generation in September, the company has seen "a real uplift in listings created, listing time, and completeness of listings," Colburn said. However, as the tool was launched recently, a company spokesperson said that specific data was not yet available.

"Aside from the direct user benefits in terms of efficiency and listing quality, we have also really demonstrated to ourselves that users value features that use generative AI to reduce effort on their end," Colburn said.

Ultimately, Depop wants sellers to list more items, and the company's goal is to make it easier to do so, he added. Automating the process with AI means sellers can list items quicker, which Colburn said would create a more robust inventory on the platform, lead to more sales, and boost the secondhand market.

What's next?

Colburn said Depop continues to look for ways to apply AI to address users' needs.

For example, taking high-quality photos of items is another challenge for sellers. It's labor-intensive but important, as listings with multiple high-quality photos of garments are more likely to sell. He said Depop was exploring ways to make this easier and enhance image quality with AI.

A challenge for buyers is sometimes finding items that fit. Depop is also looking into how AI can help shoppers feel more confident that the clothing they purchase will fit so that their overall satisfaction with the platform will be enhanced, Colburn said.

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