• 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.

The offers and details on this page may have updated or changed since the time of publication. See our article on Business Insider for current information.

Affiliate links for the products on this page are from partners that compensate us and terms apply to offers listed (see our advertiser disclosure with our list of partners for more details). However, our opinions are our own. See how we rate products and services to help you make smart decisions with your money.

• When I adopted my daughter, I had 24 hours' notice to prepare for her arrival.
• I'm a freelance worker, so it was easy to stop taking on work, but it was a big shift in how I earn.
• This article is part of "Milestone Moments," a series about financial planning for major life events.

This summer, my boyfriend and I adopted a newborn daughter — and we had only 24 hours' notice once we had confirmation that she had been placed with us. Between packing baby supplies and installing the car seat we'd already purchased, I notified my freelance clients I wouldn't be available for at least three months.

I didn't want to commit to a specific time period since I didn't know how much care my baby would need. As a freelancer, I'm used to my income varying, but this would be the first time in over 25 years that I wouldn't have any steady gigs. My career is already precarious, and I had to prepare for my income to nosedive.

I tried to squeeze in extra income where I could

I didn't fully quit working, because I still had a few deadlines to catch up on. While the baby slept, I edited a client's novel. In a burst of hubris, I told one client that I could keep writing their newsletter. I assumed I could squeeze in work around my daughter's schedule.

I didn't realize just how much juggling I would do during my spare hours — laundry, dishes, thank-you cards for the influx of gifts we received, organizing my things and the baby's.

Ever since we saved up all our anticipated adoption costs 1 1/2 years ago, I had tried to budget for my eventual time off. I'd been saving any spare income in an investment account that kept my money liquid and paid about 5% interest. On paper, my savings could cover my half of our mortgage and bills for at least a year, and my boyfriend, who has a full-time job, was happy to cover the rest.

But even though I know that I'm saving us the $40,000 to $50,000 a full-time nanny would cost, it's been extremely hard for me to stop working entirely. The idea that my savings might run out and leave me to borrow spending money from my boyfriend feels far too old-fashioned for someone who's considered herself a feminist since she learned what the word meant.

I want to keep working, but I love being a mom

Now, with my daughter sleeping through the night, I've found myself full of creative ideas begging to be put down on paper. I want to work, and I'm very grateful that I can make that choice, rather than having it made for me.

The three of us could live comfortably on my boyfriend's salary. Nevertheless, not having any income isn't something I can handle emotionally. As a child of divorce, in which money was a major factor, I worry that relying solely on him to provide for us could lead to resentment on his part, and leave me behind in the job market if we ever split up.

Because of that, I'm about to return to my part-time work-from-home copywriting job and have been taking on freelance writing assignments. I considered hiring a babysitter to free up my time, but the difference between my hourly rate and theirs wouldn't make it worthwhile. Furthermore, I'm 49 and waited a long time to fulfill my dream of becoming a mom.

I know that "having it all" isn't possible. I can't simultaneously give 100% to my job and 100% to being a mom. In just these first few months, there have been plenty of times when I've been pulled from my work upon seeing my baby's smiling face. Taking the time to have an impromptu dance party or blow gently on her face brings her more joy than I could have thought possible.

I'm earning the amount that's right for my mental well-being

One necessary expense has been my mental health. I had stopped seeing my therapist earlier this year to save money, but within two weeks of our adoption placement, I returned. I also found another provider to finally obtain medication for ADHD to allow me to not feel so overwhelmed by all the tasks on my plate.

Cutting back on work — but not abandoning it — is the compromise I've settled on to fulfill my duties as a mom, satisfy my need for mental stimulation, and stay financially stable. I'm not earning anywhere near what I was before, but it's enough for bills and occasional splurges without having to micromanage my budget. I've mourned grossing six figures annually, but someday, when my daughter's older, I hope I can get back to that level of success.

I've learned that while money is important and valuable, I can be "rich" in other ways — which I recognize is a privileged viewpoint I can afford to hold only because of my partner's income. When I walk into my daughter's nursery just as she's waking up, and she beams her drooling smile at me, I feel wealthy in love in a way no amount of money could ever hold a candle to.

What's given me the most satisfaction, though, is balancing my work projects with taking care of her. I may not be able to physically tend to her needs and work simultaneously, but I have found ways to bring motherhood into my work. Whether that's sitting her on my lap during Zoom calls or writing about the reality of my life as a mom, it has made my dip in income less scary.

• Exposure to light is key in adjusting drivers' body clocks to new time zones.
• The Las Vegas Grand Prix is "the nastiest one of the season," one performance coach said.
• This article is part of "Behind the Wheel," a series about the highly competitive and high-tech world of Formula 1.

In Formula 1, sleep is a precious commodity.

The global series' 24-race calendar spans 21 countries across five continents. Teams travel from China to Miami to Italy over the course of just a few weeks — making jet lag a constant problem throughout the season. It's such a concern that many teams employ doctors and coaches dedicated to helping drivers adjust quickly to different time zones.

"In the case of Formula 1 drivers, sleep is right up there as one of the main things we can control to put them in the best place possible to perform," Tom Clark, a senior performance coach with the Alpine F1 Team, said. "It's a thing we prioritize very highly. Being exposed to jet lag, we can manipulate it so we're ahead of the curve."

Even now, as the 2024 season heads into the home stretch, Clark is preparing for next year, looking up available flights for the team and mapping out calendars to see how early his drivers can make it out to a race based on other team responsibilities.

"Drivers have a great many commitments, so we can't always prioritize sleep and jet lag above all else," he said. "But we start planning right away so we have the best options available to negate jet lag and put the athletes in the best position."

Monitoring light and 'zeitgeber'

When it comes to fighting jet lag, Clark said, there's one main factor to consider: exposure to light.

"Light from the sun and light from electronic devices, and the absence of light — if we can manipulate those things in accordance to where we're trying to travel, we'll be able to shift the body clock closer to that given time zone," he said.

As an example, Clark points to Esteban Ocon, the Alpine driver with whom he works most closely. In preparation for heading to Las Vegas this week — about a nine-hour time shift from Ocon's home in Switzerland — Clark began shifting the driver's bedtime and wake-up time later and later last week.

"We also look at his timing to light exposure, which we try to replicate to the time zone he's traveling to," Clark said. "From a basic first principle, that's what we do fundamentally to thrive in the new environment."

Additionally, Clark closely monitors Ocon's "zeitgeber" — a German word for external circadian time cues that contribute to the body's clock. This includes physical activity and fitness, socializing, and eating.

"All of those have an influence on moving the body clock closer" to the new time zone, Clark said, adding: "But it's light that is the most influential, so that's what we prioritize the greatest."

'Las Vegas is the nastiest one of the season'

Plane travel is another factor. When traveling west, Clark wants his drivers to take daytime flights so that they stay awake. When flying east, he encourages them to sleep on flights — particularly when the series heads to Australia, which entails about a 24-hour door-to-door travel period.

With Formula 1 heading to Las Vegas this weekend to kick off the final triple-header of the season, Clark said the battle against jet lag would be particularly important.

"Las Vegas is the nastiest one of the season," he said, adding that because the race happens so late — the Grand Prix begins about 10 p.m. local time — drivers have to modify their sleep schedules so that they essentially become nocturnal, sleeping during most of the day.

"If you're like Esteban and you get a huge amount of sleep, he effectively will sleep the entire daylight hours of Las Vegas — which actually might be quite a normal thing for most Vegas visitors and tourists," Clark said with a laugh. "It's a bit of a weird way to live, but it's a necessity to cash in on the sleep opportunities that we have. We use other means to help with what we lose from not seeing the sun, like vitamin D supplements. We'll have to contend with that during the week."

Once the Las Vegas Grand Prix ends, the series immediately shifts to Qatar, meaning every team member once again has to rapidly adjust their body clocks.

"Effectively, you're doing a full circulation of the globe in time zones in the space of just a couple of weeks," Clark said. Last year, when Las Vegas was also part of a triple-header, many people discovered they could "continually be in a state of sleep deprivation and poor quality of sleep if you don't prioritize it," he added.

Clark began working with Alpine in 2018 in a performance role and said he viewed battling jet lag as an "elephant in the room" when it came to race prep. "We were doing everything we could from a training, nutrition, and recovery standpoint, but when it came to sleep, there wasn't much in place," he said. "That's where my appetite came from to pursue and understand jet lag more."

Most Formula 1 teams, he said, now task their performance coaches and doctors with monitoring drivers' sleep patterns and adjusting them to new time zones.

Outside Formula 1, Clark is pursuing doctoral work on jet lag — a topic that, he said, is not studied extensively in academic literature.

"Jet lag itself is a hard thing to research and understand just by the nature of it," he said. "You can study it in a lab environment, but you can't replicate getting on a plane, the large amount of time in the air, all the stresses you go through at the airport, and arriving in a widely different culture and environment."

That makes Formula 1 an ideal industry in which to conduct this research, with the sport featuring perhaps the most condensed global travel of any other sport series.

"I've been working within the Formula 1 population and yes, it's not the easiest thing to fit in around my day job," Clark said, laughing. "But it's fascinating, and I'm enjoying it very much."

This article is part of "Workforce Innovation," a series exploring the forces shaping enterprise transformation.

When Wex, a payments platform based in Portland, Maine, set an ambitious goal to double its revenue, to $5 billion, within five years, it recognized that achieving this would require changes in its operational approach and strategic focus. In 2022 it created the role of chief transformation officer and tapped Kristy Kinney, who previously led the company's pandemic response, for the job.

Kinney's mandate touched every aspect of Wex's operations, including adopting generative artificial intelligence in call centers, standardizing project-management systems, and identifying new revenue streams. Wex says Kinney's led 230 initiatives, hit 2,300 project milestones, and worked with and advised more than 100 leaders across the organization.

"We were intentional about not just delivering outcomes," Kinney said, adding that a lot of the change "was about building a culture of always-on transformation in our workforce."

As companies across the US confront complex challenges that require overhauling strategies, reimagining business models, and adapting workforce dynamics, many are appointing chief transformation officers to drive these changes. Boston Consulting Group said it found that CTO hiring surged by more than 140% from 2019 to 2021, led by companies in consumer and industrial goods and financial institutions.

Alicia Pittman, the global people team chair at Boston Consulting Group, said the trend reflected a shift in how organizations manage change. She told BI these specialized leaders are appointed to head up specific cross-functional projects and eventually integrate their work into everyday operations. The role is often transitional.

"Their job, in my opinion, is to sort of put themselves out of a job," Pittman said.

Ravin Jesuthasan, a global leader for transformation services at the consulting firm Mercer who wrote the book "The Skills-Powered Organization," said that while this position was relatively new in the array of C-suite roles, it was emerging as "one of the most pivotal for navigating the future of work."

"It used to be that an organization would do a major transformation every eight or nine years or so, but today, due to the velocity and volatility of change, companies no longer have that luxury," he said. "They now need a dedicated leader whose job it is to look around corners, stress-test existing strategies, and figure out when to pivot if necessary."

So what exactly does a CTO do?

The C-suite has expanded over the past few decades and now brims with new titles.

The core figures, including the CEO, the chief operating officer, and the chief financial officer, focus on delivering quarterly results. Other positions center on functional areas like technology, human resources, and marketing, and strategic areas like employee engagement and sustainability.

Jesuthasan said that among these newer roles, the transformation officer stands out as forward-looking. They're tasked with preparing the organization for the future. "They help see what's coming and identify potential disruptions," he said.

In addition, he said, they must deeply understand strategy and its implications for the organizational structure. They need to be adept at connecting different areas of the business. "CTOs help the organization develop a mindset of perpetual reinvention," he said. "They have the curiosity and willingness to challenge the status quo."

He added that strong people skills are also critical for CTOs. They need to have credibility with other executives, the ability to run experiments and test new ideas, and the skills to execute effective change management while bringing employees along.

Being a chief transformation officer, Jesuthasan said, is akin to "building the train while you're driving it down the tracks."

Brandon Batt, the chief transformation officer at Quadient, a company focused on digital transformation, knows this all too well. Batt, who was appointed in 2019, helped orchestrate sweeping changes at Quadient, including streamlining the company's divisions and simplifying the workflows in various departments.

"At the end of the day, my function is here to be the support, the glue, and sometimes even the driver behind change that's needed in the business," he said.

Change is a process, of course. Can a CTO's transformation efforts ever truly be complete? "In today's dynamic landscape for technology companies, I am not sure we will ever say, 'Mission accomplished,'" Batt said.

"We just announced a new plan for 2030," he said. "It's demanding, but leaning into it is where the magic happens."

'Change is hard'

The demands of managing organizational transformation are great, especially when initiatives span disciplines and address issues such as technological advancements, industry shifts, and evolving customer trends.

"Change is hard, and it can burn people out," said Chengyi Lin, an affiliate professor of strategy at Insead who studies digital transformation.

Lin believes the CTO role should be viewed as transient, ideally lasting two to five years. "I say this with empathy and sympathy for the individual as well as for the organization," Lin added.

C-suite titles have an important "signaling function," he said. Appointing a CTO sends a message to workers and stakeholders that the organization is committed to change. Making the role permanent could dilute its significance and risk suggesting the company is in a constant state of flux rather than pursuing meaningful transformation.

Lin argued that concluding the role after a finite period doesn't mean the transformation is complete — "it means that it's eventually folded into business as usual."

He described this approach as critical for maintaining employee engagement. Gartner has found that the average employee experienced 10 planned enterprise changes in 2022; in 2016, that number was two. It also found that workers' enthusiasm for supporting enterprise change dropped significantly over the same period.

Kinney recently wound down her role as chief transformation officer at Wex. The company is continuing to work toward its $5 billion revenue goal; revenue was $2.55 billion at the end of December last year. And Kinney has transitioned to a new position as SVP of health & benefits growth. This role involves integrating her transformation work into Wex's daily operations, what she refers to as "operational excellence."

"I used to joke that if I was in that job after two years, I ought to be fired," she said.

• Alaska Airlines partnered with Air Space Intelligence to use an AI tool that suggests flight routes.
• The tool, Flyways AI Platform, factors in data such as historical flight traffic and predicted weather.
• This article is part of "CXO AI Playbook" — straight talk from business leaders on how they're testing and using AI.

For "CXO AI Playbook," Business Insider takes a look at mini case studies about AI adoption across industries, company sizes, and technology DNA. We've asked each of the featured companies to tell us about the problems they're trying to solve with AI, who's making these decisions internally, and their vision for using AI in the future.

Coordinating airline flights seems easy on paper. Nearly all travel routes are planned months in advance, and they're designed to ensure there aren't too many aircraft flying at one time. But frequent airline delays show that this seemingly simple task can become mind-bogglingly complex.

One out of every five flights in the US is delayed by at least 15 minutes. "The fundamental problem is that when a human being sits down to plan a flight, they only have information about their one flight," Pasha Saleh, the head of corporate development at Alaska Airlines, said.

To solve that, Alaska Airlines partnered with an AI startup called Air Space Intelligence, the creator of the Flyways AI Platform, which uses artificial intelligence to suggest optimal flight routes. The partnership started three years ago and was renewed in August. Now, half the flight plans reviewed by Alaska Airlines' dispatchers include a plan suggested by Flyways.

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

All major airline flights are logged with the Federal Aviation Administration and generally filed at least several hours ahead of time. Most commercial passenger flights follow common routes flown on a schedule.

In theory, that means air traffic is predictable. But the reality in the air is often more hectic. Saleh said that air-traffic control is "often very tactical, not strategic."

That leads to last-minute diversions and delays that inconvenience passengers and cost Alaska money as pilots, crews, and planes sit idle.

"Airplanes are expensive assets, and you only make money when they're flying," Saleh said.

Key staff and partners

Alaska Airlines and ASI worked in partnership from the beginning of the partnership.

Saleh met Phillip Buckendorf, the CEO of Air Space Intelligence, in 2018. Buckendorf wanted to use AI to route self-driving cars. Saleh wondered whether the idea could be applied to airlines and invited Buckendorf to visit Alaska Airlines' operations center.

"He looked at those screens expecting to see something out of 'Star Trek.' Instead, he saw something one generation removed from IBM DOS," Saleh said, referring to an operating system that was discontinued over 20 years ago. "Pretty much on the spot, he decided to pivot to airlines."

The resulting product, Flyways, was adopted by Alaska Airlines in 2021.

While Air Space Intelligence developed the Flyways AI Platform, it did so in close cooperation with the airline's stakeholders.

"Airlines are very unionized environments, so we wanted to make sure this wasn't seen as a threat to dispatchers," Saleh said. Alaska Airlines used dispatcher feedback to hone Flyways.

Flyways now works as an assistant to the airline's dispatchers, who see its options presented when creating a flight plan.

AI in action

The partnership between Alaska Airlines and Air Space Intelligence began with a learning period for both organizations.

ASI's staff shadowed the airline's dispatchers to learn how they worked, while Alaska Airlines learned more about how a machine-learning algorithm could be used to route traffic. Saleh said ASI spent about 1 ½ years developing the first version of the Flyways AI Platform.

Flyways trains its AI algorithm on historical flight data. At its most basic level, this includes information like a flight's scheduled departure and arrival, actual departure and arrival, and route.

However, Flyways also ingests data on less obvious variables, like restricted military airspace (including temporary restrictions, like those surrounding Air Force One) and wind speeds at cruising altitude. Even events like the Super Bowl, which causes a surge in demand and leads to airspace restrictions around the event, are considered.

Saleh said Flyways connects to multiple sources of information to acquire this data and automatically ingests it through application programming interfaces. Flyways then runs its AI model to determine the suggested route.

"Suggested" is a keyword: While Flyways uses AI to predict the best route, it's not an automated or agentic system and doesn't claim the reasoning capabilities of generative-AI services like ChatGPT.

Dispatchers see Flyways' flight plans as an option in the software interface they use to plan a flight, but a plan isn't put into use until a human dispatcher approves it.

Did it work, and how did leaders know?

Alaska Airlines' dispatchers accept 23% of Flyways' recommendations. While that might seem low, those accepted routes helped reduce Alaska Airlines' fuel consumption by more than 1.2 million gallons in 2023, according to the airline's annual sustainability report.

Reduced fuel consumption is necessary if Alaska is to reach its goal of becoming the most-fuel-efficient airline by 2025. The airline also ranks well on delays: It was the No. 2 most-on-time US airline in 2023, with some of the fewest cancellations.

Meanwhile, ASI has grown its head count from a handful of engineers to 110 employees across offices in Boston, Denver, Poland, and Washington, DC. In addition to its partnership with Alaska, the company has contracts with the US Air Force and received $34 million in Series B funding in December from Andreessen Horowitz.