United’s tech chief reveals the destiny of ‘Skilled Mode,’ free Wi-Fi and extra

Of all the U.S. airlines, United Airlines has perhaps the most impressive customer-facing technology.

Its app consistently wins awards, and the carrier has invested thousands of engineering hours in building new features. Some of these include an all-in-one delays and cancellations center, Live Activities for iPhone users, an agent-on-demand service and much more.

Outside of the app, United’s text message-based day-of-travel reminders have become even more personalized and helpful than ever before. On a recent trip through Chicago, there was a text message waiting for me when I landed; it told me my connecting information, along with a personalized map and walking estimate to the new gate.

On another trip, I was traveling on a brand-new Boeing 737 MAX 8 with larger overhead bins. Before boarding, I received a text with a GIF showing me how to side-load my bag to maximize space.

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“It’s really just about taking as much friction out of the travel journey as we can,” Jason Birnbaum, United’s chief information officer, said in an interview with TPG at the airline’s recent event with Apple related to Bluetooth-enabled planes.

At the event, Birnbaum and his deputy, Grant Milstead, vice president of digital technology, spoke with me about the future of United’s tech efforts.

Here’s what you can expect.

Over the past few months, there’s been a concerning development on United’s website and app: Expert Mode has been disappearing for many users despite having this option enabled in their profile.

In case you’re not familiar, Expert Mode lets you see available fare classes, including award and upgrade availability. With this additional information, savvy flyers can get more insight into whether their upgrade might clear or whether award space might open.

Suffice it to say that for many power users, myself included, Expert Mode is a must-have feature.

That’s why so many readers have reached out to me over the past few weeks asking me what’s going on; some fear that this option will be eliminated completely.

Well, there’s some good news. Milstead confirmed that Expert Mode is here to stay.

“We’re really focused on meeting travelers where they want to be and allowing them to shop the way that they want to shop. Expert Mode is something that we’ve supported and we’ll continue to support,” he told me.

That said, reading between the lines, I wouldn’t be surprised to see this feature phased out in the coming years. Milstead talked broadly about how revenue management is always experimenting with personalization as it relates to fare classes — a project that might render Expert Mode no longer useful.

For now, I’d mark this one as developing, but as Milstead confirmed, Expert Mode “is something that we’ll continue to maintain, at least in the short term for sure.”

Free Wi-Fi is becoming a reality on more and more airlines both in the U.S. and abroad. Delta Air Lines wasn’t the first carrier to make Wi-Fi free, but it certainly sent shockwaves throughout the industry when it turned on complimentary access earlier this year.

While United offers free messaging, it still charges $8 to $10 on domestic and short-haul international flights (and much more on long-haul segments) for internet access.

I asked Milstead whether Wi-Fi will eventually be free.

“I would say the price right now is very good. I think it’s really a modest price point,” he said. “I think it hits both a business customer and a leisure customer. And the most important thing for me is we’re consistent.”

Free Wi-Fi “hasn’t been our focus,” Milstead added. Instead, the team is focused on delivering a reliable internet connection — something the airline struggled with a few years ago.

The airline has since made significant progress, and I haven’t had an inoperable Wi-Fi system on a United flight in more than six months. Along with upgrades to existing systems, United’s new planes are outfitted with Viasat antennas, providing access to one of the most reliable satellite internet providers in the world.

Last year, United updated its iPhone app with support for Live Activities, bite-size notifications that appear on the lock screen and Dynamic Island on supported iPhones.

I’ve found these notifications incredibly useful (especially the boarding countdown), and I’m clearly not the only one. United now sees more than 800,000 boarding pass impressions per day, Birnbaum said. That number has grown pretty significantly since the introduction of Live Activities.

Given the popularity, it’s not surprising to hear Milstead say that United is going to “continue to expand our capabilities there to ensure that it’s really easy for customers to get to exactly what they want.”

While about 75% of United app users are using iPhones (Milstead included), United has something coming for everyone else.

“Android has a lot of capabilities to put similar information on the lock screen, and we’re definitely exploring that. So you’ll see some of that down the road,” Milstead shared.

Meal ordering will be improved

Preordering your meal isn’t a new feature for United, but it’s one that’ll improve in the coming months.

Right now, the system is pretty wonky. It opens five days before your flight, which is when you typically receive an email inviting you to select your meal choices.

You could also search for the “select meal” button on your trip confirmation, but it’s pretty hard to find for infrequent United flyers. (You need to open the reservation, click “flight details” and then wait a few seconds for the meal option to switch to a hyperlink for the ordering system.)

United is aware of these issues, and it’s working to address them. Additionally, the airline will “expand the period of time the meal ordering is open,” Milstead shared.

If United is looking for inspiration, it can take a page from American Airlines’ book. The Fort Worth-based carrier opens meal orders 30 days before your flight. (I can’t be the only one who gets excited about preordering my airplane meal an entire month in advance.)