Keeping Commerce Human: Etsy's Tim Holley on Ten Years of Marketplace Growth

Holley left Etsy for a year to lead product at SoulCycle, drawn by a theory that fitness and wellness are the proactive side of healthcare. He came back anchored on a product that adds value to other people's lives, which at Etsy means helping sellers make sales, and on working with people he learns from and enjoys. He recalls an engineer who was a standup comedian and pushed the boundaries of the daily standup.

Asked about the 2017 transition under CEO Josh Silverman, Holley calls it hard, and notes it coincided with layoffs. Many employees had their identity tied up in Etsy, and the company had an entrenched consensus culture that produced thoughtful products but was slow. The business needed to launch faster and have a predictable way to drive gross merchandise sales, its north-star KPI.

Two things stood out to him as leadership moves: making GMS the drumbeat in every meeting and the yardstick for launches, and bringing an outside-in view of competitors, since buyers shop everywhere even though no one competes with Etsy head-on. He adds that Silverman told a clear narrative consistently, pairing clarity on the goal with clarity on why. Etsy's guiding principles include digging deeper and minimizing waste, which matter for a company of just over 2,000 people.

When the CDC mandated face masks in early April 2020, Etsy went to sleep with typical April traffic and woke up to something like Black Friday. Sellers who knew how to sew could make masks easily, so supply rose to meet demand, and Etsy did something it had not done before by calling on sellers to make them. Daily standups tracked what to change.

The team worried some sellers could not keep up, so staff phoned them to ask how they were doing. Some said it was squarely in their wheelhouse, while others asked for a pause to catch up on orders. Holley says it was a powerful reminder of the old-fashioned practice of asking what customers need at that moment.

The next challenge was keeping the influx of new and reactivated buyers by showing Etsy sells far more than masks. That pushed the company toward retention and frequency, which are harder to test than a purchase in a single visit because you wait 30, 60 or 90 days. Internally, the team tried frequent coffee chats but learned they were repeating themselves and adapted to what each person needed.

Etsy focused heavily on the supply side early, with studio visits to sellers' workshops and homes and hack weeks that brought sellers into the office. Later the emphasis moved to a world-class buyer experience, because with over 100 million unique items buyers need confidence in goods from sellers they have never heard of. That raises the importance of structured data and customer reviews.

Holley says the sequence was not linear, since supply without demand or demand without supply is not a marketplace, and balancing them is more art than science. Today he frames the marketplace's job as helping a seller make sales, so Etsy needs qualified buyers. That does not mean every team builds buyer features, as a team still focuses on listing, managing and fulfilling, and Lenny notes Airbnb went through the same shift from hosts to guests.

At the top level there is no supply constraint, though specific subcategories sometimes need more inventory, and the real challenge is helping buyers choose among many results. Etsy uses its data to guide sellers, such as advising more photos or timing a sale, and uses the buyer experience to signal what matters, for example highlighting fast responses to messages. Seasonality means the priority for sellers changes, since they are business people with limited time.

Holley admits Etsy is often surprised by what works and what does not. Reviews are long-running winners, especially buyer review photos that show an item in someone's home, which help the next buyer judge size and colour. Behavioural-economics signals and nudges, such as noting there is only one of an item, help buyers feel confident choosing from 100 million listings.

Small effort can bring big reward: a one-line copy change in the cart stating that Etsy offsets carbon emissions from every delivery resonated with buyers and lifted conversion. Holley agrees with Ronny Kohavi's figure that around 80 percent of experiments fail. Lenny shares Airbnb parallels, such as a rare gem icon, while Holley recalls a bug that rendered half a star as a horse emoji.

Most Etsy changes are A/B tested, reflecting its engineering heritage, but Holley calls finding other validation methods a growth edge. Experiments are the highest bar for proving causality, but they can miss larger net-new work, and retention and SEO need different methods such as cohorts over time. Sellers' sales and discounts are honored regardless of test results, with pre-post analysis used instead.

On the seller side, Etsy once showed up at craft fairs such as Renegade to tell makers it existed, and today sellers recruit each other through word of mouth and the Teams community. On the buyer side, a long tail of inventory suits SEO and Google Shopping, where someone looking for something specific finds not only an item but similar options. Lenny adds that early sellers drove early buyers, and Holley notes a seller is also a buyer of adjacent goods.

Etsy tried referral programs years ago. The buyer program was not a huge success, partly because the company then did not value a new buyer's future purchases as it does now. For sellers it used the 20-cent listing fee as currency, giving listing credits that helped in certain markets, though not a huge growth driver, and Lenny notes it limits fraud.

For retention, Holley describes thinking in terms of the habit loop, with a trigger and a reward. If a buyer favorites an item, that shows intent, so Etsy can bring them back when it goes on sale or is nearly sold out, using an updates feed and push notifications. The aim is to close the loop in a way that is valuable to the buyer.

Holley credits Etsy's ability to coexist with Amazon and eBay mostly to its brand, which signals unique inventory, combined with policies that protect the integrity of the marketplace. The supply is largely user-generated, so clarity about what may be sold differentiates it. The current expression is "keep commerce human," which shapes decisions, and a drone drop-off with no human touch would not feel very Etsy.

On the pressure to add other kinds of supply, he says Etsy takes policy enforcement seriously and that the work is never finished. To help sellers who cannot make enough by hand, the company evolved production assistance, as long as sellers understand how and by whom items are made and have a relationship with their partner. Gray areas are harder than clear legal violations, and teams work on intellectual-property enforcement.

On the graduation problem, where successful sellers might leave to run their own sites, Holley says fees are low and competitive, sellers use multiple channels, and Teams makes the platform sticky. Building and driving traffic to your own site is neither cheap nor fast. Etsy Studio, a craft-inspiration marketplace, was shut down because it did not fit the 2017 refocus on short-term sales and a core marketplace with ROI-positive marketing.

Etsy extends the classic three-legged stool of product, engineering and design to five by adding insights partners from research and analytics, and marketing partners. Holley admits a five-legged stool needs a flat surface but argues that blending viewpoints is the best path, and he rejects the idea of the PM as mini-CEO. His CPO's line is that you do not need the best ideas, but you must choose the best ideas.

The PM is accountable for decisions and for owning what comes next when an experiment fails, though that is no permission to ignore others. When data is not clear, the product person steps forward. Org design follows strategy through what Etsy calls the product stack: core customer teams, partner teams such as payments, enablement teams such as recommender systems and design systems, and an infrastructure foundation.

When hiring PMs, Holley looks for three things: real excitement about collaboration, decisiveness even with plenty of data, and curiosity or a growth mindset, since a small organization means shifting priorities. His favorite interview formats are live case studies and asking what a candidate has taught themselves.

The framework Holley returns to most is a weekly focus: write down what you will concentrate on this week and reflect on what you did last week. Doing it consistently reveals patterns, such as certain work taking longer than expected or seasonal tasks that need space. His team posts these priorities, not tasks, in a Slack channel on Mondays, a once-a-week higher-level standup.

In the lightning round he recommends Team of Teams by Stanley McChrystal for pushing decisions to the edges, Let My People Go Surfing by Yvon Chouinard, and The Power Broker by Robert Caro. His motto is to go all in, and the baby-tracking app Nara Baby is a favorite recent product find. The standup-comedian engineer, he reveals, is now a full-time comedian.