Like Gilt, they offer quality products at a discount to standard retail, and their site features rich descriptions and photos.

They’ve also taken advantage of some best practices in flash sales, including:

• Daily emails to introduce the latest offering and drive traffic
• Limited quantities
• Time-limited sales
• Countdown “expiration” timer after you’ve added something to your cart

The last item is key, as I believe it’s one of the things that makes Gilt so successful: urgency.

Items are reserved for a limited time (10 minutes) when you add them to your cart, but once the time expires your items are no longer reserved and anyone can buy them right from under your nose.

Seeing that timer count down the seconds creates a sense of urgency and drives many people to buy things they might not otherwise, simply out of fear that they’ll lose a great deal to some other shopper. Having had a couple items purchased out from under me on Gilt, I know first hand the feeling of loss, which only reinforces the urgency on subsequent sales.

Lot18 is obviously taking advantage of this same tactic, but they have one glaring flaw.

With Gilt, when the timer expires the items remain in your shopping cart, but are marked as “no longer reserved” in red text. That means they’ve been released back into the wild and could be purchased by anyone. It looks threatening and is often enough to make you pull the trigger if you want the items.

With Lot18, however, when an item expires it is deleted from your shopping cart entirely. It doesn’t matter if you had 1 bottle or 5 cases in your cart – everything gets deleted when the timer runs out, and there’s no history of what you looked at or added.

I’ve experienced this first hand on Lot18 a number of times, but the reason I’m writing about it now is that yesterday I was halfway through the checkout process when the timer ran out on me and all my cart contents were deleted. I had just selected my shipping address and was about to confirm payment details when I hit an error page telling me the timer had expired.

I had to start all over again, and it was infuriating.

This may seem like a small problem, but in fact I think it’s indicative of a bigger issue. Lot18 is breaking a cardinal rule of e-commerce: make the checkout process as frictionless as possible.

Most smart retailers like Amazon and Gilt keep items in shopping carts as long as possible. The shopping cart almost serves as a way of bookmarking items that you like, so you can return to purchase them at any point. Heck, Amazon takes this to an extreme and even has a “save for later” feature that archives items instead of deleting them from the cart entirely. The goal should be obvious: putting things in front of customers reminds them that they might want to make a purchase.

Lot18, on the other hand, not only deletes items as soon as the reserved timer expires, but it includes the checkout process in that time limit! It doesn’t matter if you’re entering payment info – if you’re too slow, you get kicked out and have to start the entire buying process from scratch, finding each wine you want, selecting the quantity, adding it to the cart, and then re-initiating the checkout process.

I emailed Lot18 about this flaw, and I received a standard response saying the timer was necessary given limited inventory and the need to release items back into the pool of available wine. Yeah, I get that, but it doesn’t address the actual problem.

I suspect this is a flaw in Lot18′s fundamental architecture. Gilt built the timer and reservation process separately from checkout, whereas for Lot18, adding to cart = reserved. So “un-reserving” an item probably requires deleting from the cart.

These two things should be decoupled. Reserving should not be handled the same as adding an item to the cart. The shopping cart should always contain a list of items I’ve added, unless the item is completely sold out and unavailable (and even then, Gilt let’s you add yourself to the “waiting list” in case it becomes available again).

I’d be very curious to split test this feature on Lot18 and see whether it makes a difference on conversion. I also wonder what their cart abandonment rates are and how many people make a purchase after the timer expires.

I don’t know what back-end choices Lot18 has made in building their timer and shopping cart, but this should be an easy fix and one they should seriously consider implementing. Interrupting the checkout process is a major no-no. If someone’s trying to give you money, don’t stop them!

If the agencies that birthed this malnourished horror of a baby bothered to consult a product designer, that designer should be publicly flogged for crimes against the citizens of the SF Bay Area.

I recently switched to the new Clipper Card system which is supposed to unify payment options across most of the major transportation agencies in the Bay Area. In theory Clipper should be totally awesome – one card to pay for all your transit needs, with built-in discounts and the ability to load your card via cash, ACH, credit cards or commuter checks.

In practice, however, it sucks.

I won’t go into all the wonderfully creative ways in which Clipper fails (many of which are documented here), but rather I’m going to focus on the special hell that is Clipper’s website, and in particular its Autoload functionality (or lack thereof).

Clipper’s Website – An Exercise in Futility

I set up Autoload for BART’s high-value discount ticket ($45 for $48 in credit) when I first got a Clipper Card six weeks ago. In order to qualify for the Autoload discount I had to give my credit card info, which I dutifully entered into their system.

Today I wanted to check on my Autoload settings and see which credit card I had used to set up Autoload, so I went to the Clipper website and logged in. I didn’t see a link to “edit” Autoload, so I went to the next most obvious place and clicked the “Set Up Autoload” menu link. That was my first mistake. As you can see below, there is nowhere to edit one’s Autoload info.

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Only mildly annoyed at this point, I went to Clipper’s Frequently Asked Questions and found instructions on how to edit Autoload. Mostly straightforward, if a tad unintuitive.

Boy was I in for a surprise!

It turns out that the FAQ is completely wrong. The link it references does not exist!

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Not one to give up easily, I started exploring the page and noticed a “change billing information” link. “I wonder what that does,” I thought to myself. So I clicked it.

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Turns out what it does is scare the hell out of you!

Before I can continue my wild goose chase I must first accept terms of service that authorize Clipper to charge me. Keep in mind at this point I’m still just looking for information on my existing Autoload settings. I’m not trying to purchase anything or authorize a payment. Doesn’t matter. I have to authorize payment first.

Another fun fact, as I later learned, is that you have to agree to these terms EVERY TIME you return to this screen. It’s a mandatory step in the process that never goes away, no matter how many times you check the little box. Isn’t that super?!

Ok… I’ve made it this far, so out of morbid curiosity I’ll agree to the Terms and Conditions just so I can keep playing this demented game.

(click to enlarge)

What does the next screen hold for us…

Ah ha! Address and billing information! Maybe we’re getting closer!

But wait. What is this?

It’s actually just address information. Where’s my credit card info? I know I gave you my credit card information.

In fact, this screen brings up a whole bunch of questions:

• Why don’t you tell me that you still have a credit card on file for me?
• You do still have a credit card on file for me, right? It didn’t disappear, did it?
• Which Autoload product(s) is my billing info linked to? I have to set up Autoload separately for each transit agency, so which agency or agencies does this billing info pertain to?
• Where did the left-side navigation menu go?
• And most importantly, where the hell do I EDIT MY AUTOLOAD SETTINGS?!

(click to enlarge)

I scoured this page for a few minutes, mulling over all the above questions, when I finally noticed the navigational “breadcrumbs” across the top of the page:

Hmm… that looks interesting. I wonder what “Edit Autoload” does. So I clicked.

Eureka!

Finally I found it! The place to edit Autoload! That only required 5 completely unintuitive steps and ignoring Clipper’s incorrect FAQ entirely.
 

(click to enlarge)

The astute observer will notice that on this page the only thing to “edit” is actually the option to disable Autoload entirely. That’s it. There is no payment information, no ability to choose a different credit card for Autoload. Just disable.

And if you try clicking the “Update” button without having selected the disable option the website will present an error message instructing you to choose “an” option before proceeding. I think it should tell you to choose “THE” option, since there’s only one thing to do!

I Could Write a Book

I wish I could say that Clipper’s suckage was limited to just the Autoload fail I’ve highlighted in this post. Unfortunately, the crimes against usability and design are so numerous that they could provide content for an entire textbook on how NOT to design a website. It’s tragic, really, because the Clipper Card idea has such amazing potential and, if implemented well, could be a delight for its users.

Instead, it’s incredibly frustrating and makes me want to throw things.

I wish I knew how this website and the procedures behind the Clipper Card were designed. We live in the SF Bay Area, home to some of the best product and web designers in the WORLD, and yet we have a transit payment system that feels like it was a high school project.

I’ve submitted feedback to the MTC, but I’m not holding my breath that any of this gets fixed any time soon. I would like to state publicly, however, that I will happily offer the MTC my services and advice on how to improve their consumer website. My designer friends and I would be happy to fix some of the more egregious problems in an effort to make the system better for everyone.

If you’re listening, MTC, please do something about your website, whether or not you enlist my help. Clipper Card users everywhere would thank you (and you’d probably save some money on customer service).

Be that as it may, Twitter just launched a redesigned homepage a few minutes ago, and it features search and topic trending front and center.  As I just tweeted, if there was any doubt about the direction Twitter might be headed as a company, I think the new design clears that right up.

Regular Twitter watchers should not find this surprising. Frankly, I think it makes a ton of sense. Real-time search is the new black here Silicon Valley, and Twitter is uniquely positioned to do something interesting in this space. Of course, the challenges are still great, because simply searching what people are saying or doing in real time doesn’t solve the problem of relevance, context or accuracy.

I’ve long been interested in both social search (e.g. mining one’s network for data) and real-time search, and I’m really excited to see what Twitter has up its sleeves.

P.S. Perhaps fittingly, it was launched on @Ev and @Sara‘s anniversary. Hooray for new beginnings!

In other news, death to IE!