How Craigslist’s Competition is Winning the UX Battle With In-App Chat


After all, the primary reason we continue to cling to our mobile devices and digital communication at large is the desire to communicate as efficiently as possible.

craigslist logo

When buying or selling used items online, where is the first place people turn?

Ask six people, and you may get six different answers. But a common option, or at least consideration, remains Craigslist. Perhaps because of its first-to-the-party status (est. 1995) and subsequent success, the company’s brand remains sturdy decades later, maintaining an undeniable association people have with, say, buying used bikes, kitchenware (or, uh, other things) on the internet. And by most accounts, the company continues to hum along — a brief glance of the site shows countless new items for sale each day, and in 2019 the company was reportedly earning upwards of $1 billion in annual revenue.

But as “Craigslist” remains effectively embedded into the everyday lexicon of e-commerce, the service’s user experience is not what you may expect for a leading tech company. Not least of which is its interface — Craigslist’s digital properties (it only got around to releasing an app last year) appear more like online message boards from the early 2000s. Barebones displays along with a healthy amount of spam listings seem to indicate that the site is broken or has gone unmanaged for years.

And you know what? It can be a breath of fresh air from the daily cacophony of nearly every other part of the internet. Free of jittery ads and intrusive notifications, it is endearing at times to access a site that lower cases every bit of text, one that hasn’t much updated its color schema in years, and one that is apparently unconcerned if you stay, leave, or forget about it entirely. To be sure, there is a beauty in its antiquated aesthetic, a beauty born from an apparent ethos that could define a thrift shop:

Hey, take a look around, we might have what you’re looking for, good luck.

Unfortunately, though, an increasingly-glaring omission stands out on Craigslist, derailing much of its charm and otherwise fine and unique user experience. After 25 years of existence, there is no in-app chat on Craigslist, no avenue for users to directly message one another on the platform when inquiring about an item or service. Instead, users must migrate their conversations to email or text messages in order to communicate, leaving the platform altogether and forcing them to trade on personal, unverified accounts. Quickly, users are no longer delighted by an old school UI but presented with and frustrated by a broken communication process, exacerbated by what can only be understood as the company’s anathema to change, which in turn damages its product and reputation.

Here, in 2020, is how users on Craigslist must inquire about an item for sale:

five images of craigslist's user experience when inquiring about an item

From start to finish, there are four cumbersome steps a user must take to merely reach out to another person about a for-sale item and start a conversation.

  1. Discovering the item
  2. Complete a complicated Captcha
  3. An unnecessary two-click process for accessing the seller’s email or phone number (upon doing so, the user is then shown a long, spam-like email address that provides little assurance that any of what they’re seeing is real or associated with an actual human being.)
  4. Migrate to a separate email or text platform to contact

By now, users are exhausted. Because it remains unclear if our actions are correct and we’re given no indication that progress is being made. But wait, there’s more faulty UX:

  • Once the process starts, users are no longer able to see the item in view, stripping away its price and location as the message is being composed
  • Users are subjected to putting forth their own email addresses or phone numbers, losing any sense of security or possible account verification
  • A clear lack of transparency, as users cannot confirm whether messages were delivered or read (let alone sending emoji reactions, GIFs, or using threads)

And in the last few years, Craigslist competitors have begun to exploit these UX flaws for their own benefit while at the same time leveraging in-app chat. Facebook enjoys saturation with its enormous user base, and for those who never joined or have since tired of the platform, OfferUp and Nextdoor are solid alternatives. (We’re excluding Amazon here. While adjacent, its sheer ubiquity and behemoth stature doesn’t quite qualify as a 1:1 marketplace comparison with the others.)

Among other benefits, in-app chat on these platforms helps solve the issue of different operating systems among users. As we recently explored, iOS and Android users often have a poor time exchanging text messages — for iMessage users, green SMS texts from Android devices are automatically lumped in with spam, appointment reminders, and confirmation codes. What platforms like Facebook, OfferUp and Nextdoor do is eliminate these discrepancies by leveling the playing field and rendering all messages identical, no matter the device used. This design means read receipts, typing indicators, and more are available to all users. As a result of matching UI, users have an extra sense of security knowing the person they’re speaking with is likely real and shares a mutual interest. Plus, many of the apps’ design allows users to rate sellers post-purchase, adding to the process’s legitimacy and providing a sense of security that one is avoiding any kind of scam.

Are all of these newer apps perfect? No. Because the arena still remains one where strangers are exchanging merchandise online with, at best, mild oversight and little recourse for buyers when situations go awry. Even the most flawless app in the world, if it existed, would probably never get past these issues.

But, as we’ve recently explored and experienced several Craigslist competitors, it is becoming apparent that even a few light shades of lipstick on a pig can make all the difference.

Facebook Marketplace: Changing How We Think About In-App Chat

Facebook Marketplace featuring in-app chat

Perhaps unsurprisingly, Facebook has one of the most satisfying and dynamic in-app chats on the market, its Messenger experience a longtime leader in how people around the world communicate. After all, if the company that began in a Harvard dorm room nearly 20 years ago knows one thing, it is that users crave instant gratification, immediate feedback and, most importantly, want to feel like they belong.

So, with a built-in audience of several billion, it only made sense for Facebook to launch Marketplace in 2016, a product that TechCrunch called a “friendlier Craigslist,” and one that follows a standard search, sell, and buy process.

Making connections
What stands out in the Facebook Marketplace experience is its clear commitment to connecting sellers and potential buyers as quickly as possible through verified messaging. Quite literally, the latter group only needs to complete a single CTA action (clicking “Send”) to initiate a conversation (after verifying one's identity, adding an extra layer of security).

The message’s content can be edited to a user’s liking, but Facebook has pre-filled several common (and actually intelligent) inquiries rarely found on other digital applications (ahem, Gmail). What the company also gets right is it keeps the for-sale item, its price, seller information and any other details intact while potential buyers send a message. Unlike writing an off-app email or text with Craigslist, Facebook eliminates the user’s need to migrate back to view information, helping push the conversation forward with little friction.

On the sell-side, Facebook’s app makes uploading photos and information easy by designing mobile-first, leveraging AI to help categorize and sort items. (If someone uploads a picture of a Jeep, for example, the app will identify it and immediately categorize it in automobiles.) A bonus for sellers is the access to an estimated 800 million Marketplace users (Craigslist: 55 million) and posting items to groups designed for the buy-sell transactions. Writing for MSNBC in August 2020, a reporter said that in San Francisco alone he was able to tap into a market of 24,000 people and sold “everything from a blender to gardening tools and some scuba fins. I even bartered a few old camping tents my roommate left behind for two cases of White Claw.”

In-App Chat, Without the ‘Chat’

Facebook Marketplace allows users various options to buy without direct messaging

As Facebook continues to iterate its UX in Marketplace (remember, it’s only four years old), the company is changing the way we think about in-app chat. In some cases, that means deprioritizing the traditional “chat” part while still providing ways for users to communicate.

How? By providing sellers and buyers different ways to settle on what are ultimately the primary issues: availability and price. Using Facebook Marketplace, sellers can list items by allowing potential buyers to submit flat offers for items. In some cases, that means pre-set prices (in the example above on the left, there are three). In others, potential buyers can submit custom offers (see above image, right). Then, sellers have 24 hours to accept or decline the offer. (There is also a “buy now” option on some items — laptops, other electronics are commonly sold this way — which acts much like a straight e-commerce platform, sending buyers to checkout right away.)

In short: Facebook Marketplace provides ways for sellers and buyers to agree on a sale using in-app chat that eschews traditional back-and-forth dialogue. Still, though, the chat’s purpose remains the same and central to the process by connecting like-minded parties in search of shared information that helps define an outcome requiring concurrence.

In-app chat cheat sheet lessons from Facebook Marketplace:

  • Connect users and jumpstart conversation as quickly as possible (one click!)
  • “In-app chat” can take on many forms — a mere dollar amount can be enough if delivered in the proper context

OfferUp: E-Commerce, with a Convenience Factor

OfferUp allows users to browse items nationwide with easy-to-use shipping

Since launching in 2011 and raising $120 million within its first five years, the app OfferUp follows a similar browse-buy-sell pattern for users. And after acquiring competitor letgo in March of this year, the company appears to be enjoying a boost in visibility. While still outpaced by Facebook and Craigslist, the Seattle-based company now counts roughly 20 million monthly users perhaps, in part, because of the company’s conscious effort to make women feel comfortable using the app.

And similarly to Facebook Marketplace, OfferUp positions in-app chat at the center of its experience. What differentiates OfferUp is a focus on nationwide shipping.

Coast to Coast
With OfferUp, potential buyers can sort items available for “nationwide shipping only” and are able to see the price (based on one’s zip code) before purchasing, keeping the process transparent from browse-to-purchase. The use case above shows a user searching for items related to “Looney Tunes” available for nationwide shipping at a rate based on the buyer’s location. Plus: any items that show up under this filter are guaranteed to ship nationwide, adding a sense of freedom to the search.

So if, say, a user is looking for a specific collector’s item, with OfferUp, she is able to search the entire country rather than just her surrounding area while knowing what it will cost to reach her based on her zip code. While Facebook also offers shipping and for-sale items that will occasionally appear from all around the country, the major difference is its search radius is limited to 100 miles (Craigslist: 250 miles), significantly limiting the ability to browse nationwide.

Another way to frame OfferUp’s focus on “shipping” is to simply think of it as “delivery.” Even before the seismic disruption that 2020 has become, delivery is what has set Amazon, InstaCart, DoorDash, and many more, apart — the act of tapping a few buttons and watching items show up at our door a few hours or days later is an undeniably convenient and irresistible user experience for just about everybody. And, if it wasn’t already clear before: people are willing to pay for the delivery of just about anything.

It is also worth remembering that part of OfferUp’s success is because in-app chat helps verify users and adds legitimacy and safety to the process, assuaging the anxiety around meeting with strangers for the exchange of goods. Furthermore, that anxiety can be outright eliminated when items are so easily shippable, providing a nice touchless service, not unlike Amazon.

Giving the people what they want

OfferUp allows users to buy items using a version of in-app chat

Elsewhere, OfferUp’s use of language in its app mirrors much of what Facebook Marketplace does, providing different options for users to connect, all buoyed by the spirit of in-app chat. Notice above the three CTAs. One prompts users to inquire about an item; the other to make an offer; the third for users to buy outright. (Note: not all items have three CTAs, some have just one or the other.) “At this point,” the company makes sure to say on its website, “you’re not promising to buy.” Indeed, but communication — yes, in-app chat — has begun, and both parties have a vested interest in the outcome even if it isn’t always through traditional back-and-forth dialogue.

OfferUp also seems to know that, sometimes, people just want to have a conversation like they’re used to having — i.e., some good old fashioned bartering. Well, the app lets that very thing happen rather easily, and it gets the conversation off the ground by suggesting useful prompts. It’s just one more way OfferUp bests the likes of Craigslist — putting in touch people who have a mutual interest in various items for sale.

In-app chat cheat sheet lessons from OfferUp:

  • People love frictionless UX — in today’s world, that often means speedy delivery
  • If you want users to do something specific, tell them with clear language to do that very thing
  • Leverage in-app chat for people to feel safe when using marketplace apps

Nextdoor: Turning Neighborhoods into Marketplaces

Nextdoor's marketplace uses in-app chat to help focus on community

A final example of effective in-app messaging for the browse-buy-sell space is Nextdoor, the app for neighbors keeping up on what’s going on in their area. Like Facebook, it only made sense for Nextdoor (a mobile-first app) to leverage its user base and offer a marketplace for the selling and exchanging of goods — after all, why travel downtown on the subway to check out a dresser when someone down the hall, a person you might even be friendly with, may have one?

While Nextdoor’s UI/UX seems to be a mix of Facebook feeds, LinkedIn updates, and even Twitter-like content, what helps define Nextdoor’s marketplace section is its adherence to building an app for users’ immediate surroundings and known community, one that also bends toward lending a helping hand. Nextdoor seems to understand that transactional commerce between non-commercial parties works best when user proximity leads to a safe, familiar avenue for communication — in other words, in-app chat. (Yes, there is the possibility of browsing and selling items beyond one’s apartment complex or neighborhood — this is a business, after all — but the app is designed for one to begin the process close to home.)

Sell and give back
This emphasis on community and charity in the design is most apparent on the seller’s side. As shown above, when users post an item, they’re first asked if they want to donate a portion of the proceeds to charity. (Annoying, intrusive? Nah. There is no blackhat UX practice nor any smarmy guilt tripping there — it is merely a suggestion.) Finally, just before publicly posting, users are given the option to list their item(s) in one of three geographical areas. Individual use cases and one’s ability to move a particular item will dictate the choice, but the point remains: Nextdoor, unlike its competitors, helps steer users towards their community.

The benefits of this are endless, but here is a simple one: it generally behooves people to become familiar and friendly with their neighbors. It helps build trust, support, and possibly meaningful friendships.

From our view, selling on Nextdoor is an experience that helps build a community through the trading of goods — it takes Craigslist’s impersonal and sometimes unnerving experience by shrinking our world to those who we have a vested interest in helping and getting to know beyond a one-time transaction. A cynical take might argue that this Nextdoor experience is still nothing more than free-market capitalism regardless of who is buying and selling. Fine, there’s truth there. But years of experience across all of these apps tells a different story: connecting on Nextdoor is akin to walking down the block and checking out a garage sale from your neighbor. Maybe you buy an item or maybe you don’t. But even if you don’t, maybe you know someone who does want a 50-inch armoire, and you just happen to have the truck to help move it over there.

In-app chat cheat sheet lessons from Nextdoor:

  • Don’t underestimate the power of community and charity
  • Encourage users to communicate via chat and host all conversations in one place

What's next?

Will Craigslist endure? Perhaps. Perhaps even without changing, the company’s shelf-life may last many more years, trading on nostalgia and brand awareness. Eventually, though, this stubbornness will likely catch up, as the tide is already starting to turn and companies such as Facebook, OfferUp, and Nextdoor are all poised, either on their own or as a group, to fossilize Craigslist once and for all thanks largely to an understanding of what users want and when as it relates to communicating via in-app chat.

There are many key lessons to be learned from these apps (and, for better or worse, Craigslist itself), and few of which are only meant for marketplace-based apps. From travel sites to dating apps and car services, in-app chat best practices reach many digital properties and platforms. Because the primary reason we continue to cling to our mobile devices and digital communication at large is the desire to communicate, one-on-one, as efficiently as possible. That desire still drives the majority of engagement across the most popular apps in the world.

In the coming years, the apparatus in which we participate in this communication will likely change — it’s possible the next generation is no longer carrying mobile devices as we’ve come to know them, and the future of “apps” and “chat” are experiences and designs we can’t quite imagine yet. But no matter the course they take, the need to communicate, the need to have a direct back and forth with friends, colleagues, and strangers, isn’t going to change. And if we lay the groundwork now, if we improve that communication and create the space for all of us to participate in and feel welcomed, well, we might just end up with a digital experience that brims with optimism and brings out the best in us.

One final in-app cheat sheet for the road:

  • If you’re in the business of connecting users — then connect users on your platform! In-app chat is a great place to start.
  • When possible, make it easy for buyers and sellers to ship items — this speeds up the process and helps create safer interactions
  • People like to feel good about buying and selling items, and the easier the overall communication is (read: in-app chat), the better the chances that both parties will come away with a positive experience.