Launch HN: Carry (YC S19) – We Book Travel for You on Slack

158 points by tejasmanohar ↗ HN
Hey HN! We're Tejas and Kashish, co-founders of Carry (https://carry.travel).

Carry is your executive assistant for travel. Just message us (i.e. "I need to be in Boston for a meeting at 2pm on July 1st"), and we'll get everything done for you— flights, trains, cars, hotels, Airbnbs... you name it. Carry is not a chat bot— we function like a traditional agency with in-house travel agents, but unlike traditional travel agencies that use terminals (similar to Bloomberg in Finance) or manually search websites like Expedia, we're building in-house tools to make our agents' jobs easier and help them work faster. Imagine automatically going from a customer message ("I need to be in Boston Tuesday for a 10am meeting and return for a 9am meeting Friday") to parsed trip requirements (from: SFO, to: BOS, arrive by: 10am, return by: 9am) that are then merged with your calendar and user preferences to search all data sources. Our agents then interpret the results and propose options to the user. Over time, we want to add more automation and intelligence using each user interaction as training data (but first we need volume... lol).

We built Carry because we hate booking travel— it's just way too time-consuming and inefficient. It's tedious to check multiple sites (Skiplagged, Google Flights, Skyscanner, etc.) before finding the cheapest price, filling out all of the airline information, and then, searching for a place to stay. And, even when you have all the information, choice paralysis prevails.

9 months ago, we set out to build a chat bot because we asked ourselves "Why can't Siri book travel?" Working backwards, we quickly realized why bots don't work— they're robotic, formulaic, and take lots of back and forth to convey what you want. We also realized that consumers don't know what they want, which makes it really hard to choose travel options for them. With these learnings in mind, we looked to corporate travel agencies for inspiration.

It turns out 70% of corporate travel is booked without any tool or agency— employees book their own travel and expense it. The other 30% uses tools at two ends of the spectrum— 1 old school travel agencies (think phone calls) 2) new-age corporate travel portals (imagine a clunky, worse Google Flights). We found that no one actually wants to use these tools— they just have to, and that the only people who were satisfied with the state of things were folks who had assistants they could offload the work onto.

Thus, we decided we'd create an assistant for everyone. Carry is the first travel tool built for employees-first. Employees get all the points, all the options, and the ability to save time an assistant provides. So far, we've been working with corporations directly, but today, we're doing a soft launch of Carry for individuals with a waitlist at https://carry.travel. That said, for the HN community, just email me (tejas [at] carry [dot] travel) if you want to start using us for work immediately.

If you travel frequently (or even if you don't!), we'd love to hear about the inefficiencies and pain points you've experienced while traveling that you wish a product like Carry could solve. We want to hear your feedback on the product and work with you all to develop features to save even more time.

127 comments

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Love this product Tejas, we'll be using it!
Thanks, Ilya! We're helping some folks on Segment's Sales teams :)
Congrats Tejas!
Thanks, Evan!! Get us some users at CloudFlare :)
Congrats on launching! Good luck!

I just briefly checked your website, but could not figure out if you only do business travel or vacations as well. Also, which countries is your service available in?

Hey! One of the founders here. Carry is available all over the world, but our responses can be slower outside of the hours of 8am - 2am Pacific Time. Where are you based?

For the last almost ~6 months, we've been doing top-down sales at companies, serving their teams that travel most (eg sales, implementation, professional services, etc. teams), but given demand from folks in our networks, we're opening up Carry to individuals (both for use at their jobs and not). From user behavior, we believe Carry is best for "high-intent travel", which we classify as travel that you know you have to take-- whether that's a bunch of people going to a wedding, a conference, or a business meeting-- as otherwise, users often don't know what they want.

What would you like to use Carry for?

I am from India. My use case for traveling is personal family vacation. I find it frustrating to book flights and hotels for personal vacations.
Love to give this a shot if anyone has a referral. Probably my major pain point is my team booking travel together. We'll put it on a clunky excel file or sharepoint page, people block out what they think is the travel date, factory times move and we all have to rebook or just go early/late, etc. Being able to block reschedule a group of individuals would be cool too, like grouping these individual accounts for certain types of travel.
Email me at gnomepomsky [at] gmail.com!
adaorardor is a friend that can share an invite!

But, group work travel is super interesting. Feel free to just email me-- tejas [at] carry [dot] travel directly, and we'd love to chat and see how we can help, especially if your team has a trip coming soon.

How much does this cost? I don't see any pricing information.

> We book travel on your personal card so you can get all the points.

Do you bill the charges directly to the customer's card or do they get billed by you and then you separately purchase the flight/hotel/etc?

Curious how that works regarding card data storage as you'd need likely need the full card number, expiration, and CVV to run each charge and it can't just be hash or payment token if you're passing it on to a third party for the full booking.

Great questions :-)

> How much does this cost? I don't see any pricing information.

Carry is free for individuals and small teams. We don't charge for just booking travel, but we do have upgrades available for larger teams (admin panels, constraints, etc.). What are you interested in using Carry for? Seems like you work at a large company, feel free to email me at tejas [at] carry [dot] travel.

> Do you bill the charges directly to the customer's card or do they get billed by you and then you separately purchase the flight/hotel/etc?

At the moment, most of our transactions are done the latter way (get billed by airline/hotel/etc and then separately charge the customer), but we're looking into some ways to avoid this, particularly - Tokenization: Spreedly/TokenX - Using something like VGS, https://www.verygoodsecurity.com/

Let us know if you have thoughts here! Payments are a very interesting topic

> At the moment, most of our transactions are done the latter way (get billed by airline/hotel/etc and then separately charge the customer)

One concern that comes to mind about this is if the credit card companies would consider this purchase as "travel". Like where Chase Sapphire Reserve gives triple points for travel purchases, and also has a $300 travel credit, but either of those things would only work if Chase considers your service as "travel", rather than "online service" or whatever.

You may have already worked this out and gotten it classified as travel, and if so it would just be a nice thing to put on a FAQ or whatever.

Same for credit cards that offer travel insurance as long as the flights/rental cars etc. are booked through them. They'd most likely need to see the charge from the airline in order for the coverage to be effective.
Good point. Travel Point multipliers can be achieved via setting a merchant code (MCC) of travel on charges (stripe, for example, supports this.

The trip insurance card benefit— I don’t think we can satisfy right now. We’re exploring ways to use the user’s own CC with the end vendor (eg airline) rather than us charging the user separately. “credit card tokenization” should work here (Spreedly, TokenX) but it’s non trivial due to how many vendors are in the space

Email me if either of these are stopping you from wanting to use the service, and we’ll figure out a workaround or let you know when it’s solved!

Normally insurance is still valid in case of intermediaries, your travel insurance is perfectly valid if you booked through an OLTA. Maybe it’s just a question of certification?
Congrats on the launch guys, let's get bubble tea again sometime in the future :)

I think I mentioned this before in person, but I'd like to repeat myself just so that others can chime in with whether they feel this pain point too: a lot of travel revolves around other travel arrangements (not necessarily flights) on the same day. These other arrangements are often slightly time-customisable too, but the number of combinations is obviously limited (I can't take a bus to the airport after the flight). Finding the best combination that doesn't require me to wake up at ungodly times is a hassle that I'd like to see solved.

Thanks Adhityaa! So cool that you found us on here!

You're so right, there are no solutions that focus on point A -> B door-to-door, and we've found that the reason for that is that most solutions don't know their end customer. They don't include information like home address and office addresses. The only solution that we can see handling end-to-end is Google Flights since they can easily integrate with Google Maps, for us, a very important goal is to help people manage their day of travel, not just their bookings :)

A European startup called Omio is doing this, at least partially. They used to be called Goeuro
Adding automation to this workflow seems like an exciting problem to solve!

I’m interested in seeing how you end up dealing with inaccuracies that arise in a almost-safety-critical operation. E.g, in your example, returning at 9 (even ignoring delays) would make the traveler miss their meeting.

You're right, flights/travel is so mission critical that we don't see "AI" taking over this workflow anytime soon. There will be a real person verifying every decision for the near and medium-term future. The automation component helps these real-people make decisions faster (ideal case is 30 seconds or less once it gets really good)
Linking to their Calendar would be interesting so you can know their business schedule.
Yes! We're working on the calendar integration :) We find that several business users will omit calendar because of privacy or because they don't keep them up to date, but power users of GCal would love this I think
Is your plan to continue to perform the travel booking directly? Or turn into a SaaS product (Slack, Teams<-you are here->Travel booking teams or companies) that any travel booking company can use? I'd love for our corporate travel provider to have this functionality, but we would never be able to support the use of a startup for our travel booking functionality.
We've been playing around with the SaaS idea that you described, because there are 80k+ travel agents in the US and they are underutilized! We eventually decided that performing the travel booking directly is important because that way we control the user experience, and our level of service is really the main value prop right now

We'd actually love to talk to your corporate travel provider and see if a partnership makes sense! ping me at kashish [at] carry [dot] travel? Otherwise we can get you started as an individual if your company allows it :)

This reminds me of that robo company that you could text anything you wanted to and they would book/figure it out for you. Love that you are honing your focus in to Slack and Travel. Goodluck!
Are you talking about Magic [0]? I've used it a few times for rather esoteric items and had great experiences.

(Both were booking appointments at government agencies with awful reservation systems that often were overbooked or limited availability — TSA global entry appointments and DMV appointments. It cost about $30 each time.)

[0] http://getmagic.com

Ahh, magic: the guys that stiffed me on $1,500 and then flew the entire company to the Philippines. Been dodging me for two years. They're still around and scheming, huh? Still operating out of the cardio room of that gym, I wonder?
One of the founders here. Focus is a big component to why we think Carry can successfully scale in comparison to other ops-heavy businesses, like Fin (when it was an assistant-as-a-service) & Magic. We've done the conservative math, and the economics can work out without a ton of automation but obviously with a much lower margin than we'd like (and tech can also improve the UX significantly).
Here's a killer feature everyone wants:

I want to put a date range and get the cheapest plane tickets.

Big range, I want to find the cheapest time of the year to fly and plan my vacation.

Nobody lets you do this.

Agree, this would be super useful! Have you tried Skyscanner's whole month feature? I believe they allow you to search for the cheapest tickets within a month and (if I remember right?) even within the year.
This one is the best by far, Google Flights 2nd place. Sometimes our agents even use the Skyscanner matrix for our users because it's so good.
Take a look at https://www.skyscanner.com. They have a "cheapest month" feature. All you have to do is choose your destination.

To see it, choose your flight then in the date pop-up choose Whole Month -> Cheapest Month.

I believe they also have the inverse where you can choose a month and a departure city and they'll give you destinations by price. I couldn't find it quickly though but I think they have it.

While it doesn't work amazing everywhere, I love skycanner's map feature: Pick a month and destinations and prices shown on a map. https://www.skyscanner.com/cheap-flights-map
I sometimes do the opposite for this: put my destination as my starting point, and use that to figure out which city is the best for me to fly out of.

I live near a border, and can arrange my life around a few other cities if the savings are worth it (e.g. visit family or see another city a few hours from me)

YES! I really want that too!
Google flights[1] kind of does this. If you put in an itinerary, add whatever other constraints you have (e.g. airline, flight times, fare class), and then click the calendar and wait a second, it'll eventually populate with prices under each day for changing the itinerary to that day. The cheapest day is colored in green so it jumps out.

It's not perfect, the calendar view shows two months at a time, and at times it's easier to use as starting point, but it's definitely better than clicking through 100 itineraries on an airlines slow site.

[1]: https://www.google.com/flights

Google Flights does this
Recently discovered that Google flights not only has a matrix when you're choosing dates, but also has an even better one after you've already chosen dates to view the price differences for +/- 5 days on both the departure and arrival.

Just click on "Date Grid" after you search for your query and it will give you a matrix. I can't believe I just found this!

Momondo.com does it, Cheaptickets.de as well.

Whenever I talk to my friends from the States I get the feeling no one compares flight prices. Most of them book with 'their' fav airline of choice without comparing different options.

It depends a lot on how often you fly - I prefer Skyteam partners (ie, Delta in the US) whenever I can because I fly often enough to have award status with them, meaning lounge access, priority support, upgrades in-flight, etc... I'm sure I pay them more raw dollars than I would if I booked my trips on the absolute cheapest airline in all cases, but the perks make all the difference between the flight being a chore or a moderately pleasant experience.

I have plenty of friends, though, who don't fly as often as I do and can therefore chase the cheapest fare. It doesn't matter to them if they get a flight with an airline they don't have status with, or an airline with no special perks at all, because they're not on the road often enough to qualify for those things in the first place. Raw price wins.

Travel is one of the few industries where brand loyalty still has some tangible perks (albeit decreasing every time airlines revamp their rewards programs), so especially within the US where pretty much all of the airlines fly to pretty much all of the major airports, its an approach worth considering.

A lot of credit card deals lock you into particular airlines. Either through a card branded with that actual airline, or companies like AmEx making you choose exactly one to reap benefits with.
Kiwi.com is actually really good at this. You can select flexible departure and return date, flexible departure location (eg. list of airports or simply a radius around your home) or even find the cheapest dates if you wanna stay for 3-5 nights. The features of search are best I have ever seen.
A couple companies have limited flexibility.

I recently moved out of state and want to fly back from time to time. I don't have any particular dates I care to fly on. I just want the most affordable option and I'll plan everything else around that.

You should really check out https://greatescape.co/

I'm not sure if it's a startup or an MVP or a student project at this point, but it's the closest that I've come across

https://www.kiwi.com/us/

Let’s you set travel ranges, multiple destination options, geographic areas and more. Shows you the cheapest options within the range of parameters you set. My absolute favorite vacation planner.

This is called A flex, this is very common. Sadly is one of the most compute expensive searches as you have a combinatorics order of day pairs.
I would use this if you had a Bloomberg integration, and maybe if I could share my itinerary through it. I sit on it all day except for activities to upkeep my wellbeing.
Founder here.

This is interesting! One of our friends in finance recently suggested this, too. We don't have access to a Bloomberg terminal, but we wanna look into this. Do you (or anyone else) know what it takes to ship an integration on the Bloomberg terminal? Will email you (from your profile) after the HN buzz, too :)

Also, @HN we're currently on Slack/SMS/email but if you have other platforms you'd suggest, let us know here. WhatsApp has definitely come up for some of our friends in India.

My email isn't working in my profile due to recruiters. I added you on LinkedIn.
We use a similar YC company for corporate travel, flightfox.com. I can't tell you how much money we save by enforcing corporate policies and letting them use lots of tricks to get the best possible rates.
We've heard a lot about flightfox! We're focused employee-first so that we can build a tool that employees their managers for, but that being said, several of our corporate customers have been seeing a similar cost savings because of the ability to set travel policies with Carry.

Just curious, what % of travel at your company is booked through flightfox?

How will you scale?

The reason that travel booking is so bad is because once you get too big, you start to eat the (very thin) margins of everyone in the travel industry. Then they get all defensive and, if you don't get acquired, start cutting you off or giving you crappy restrictions.

Are you competing with something like Carlson-Wagonlit Travel?

You're right-- the travel industry is built around leverage and highly political. I can't say that we've worked everything out, but we've already started navigating such situations and think they're inevitable.

One theory (though a bit fluffy) is that if we can successfully automate more and more of these processes, our costs can be dramatically lower than "traditional travel agency" competitors / margin higher.

Yes, in theory, we're competing with Carlson-Wagonlit / Amex Concierge. That actually hasn't been hard at the smaller / medium size companies interested in using us (big ones are obviously harder since they have a travel desk, etc.). In actuality, we're currently competing with companies like Concur & TripActions and the most popular way, employees just spending tons of time planning/booking/expensing travel themselves.

Do you have a background in travel space? Would be cool to chat more

I’ve had some exposure to the travel industry by working for a credit card loyalty program, but nothing formal.

I appreciate your honest reply and wish you luck!

A lot of this really feels like the people who need that would be better off with a personal assistant/secretary that remembers the person's needs and preferences.
That's the point :-)

Dedicated personal assistants are too expensive (or at least, that's the common belief). Our idea is to use a mix of computers + humans to provide a personalized experience.

"70% of corporate travel is booked without any tool or agency"

That always bothered me. We used this middle man agency ... there was no savings, I still just booked it myself for the most part. I just had to use their crappy site.

I did not understand the point of that, but man it was policy.

Exactly. I'd say many companies are worse off w/ traditional middle man agencies. They don't save time and often cost the company more money (though there are some merits in the problems they prevent, like abuse, at scale).

We look at most of the top corporate travel portals and think "worse Google Flights". We want to help the employees save time, while they want to fill a checklist for the finance team. Obviously, this is trickier than it sounds since our ideal "stakeholder" is different than much of the market, but we think it's possible by targeting teams that waste the most time coordinating travel.

At my previous company, I was once told the reason was integration with their accounting systems and enforcement / guidance around travel policy. e.g., don’t spend more than $X / night at a hotel in a certain city.

Definitely seemed like these middleman agencies were a solution to a problem faced by the finance team.

Yeah I suspect that was it.

Oddly, I don't think a lot of this stuff really accounts for the complexities in air travel.

Like I literally couldn't rent certain types of cars ... and the no cars.... all in the name of saving money.

But I could take a taxi everywhere for 150% of the cost of car rental (at least) because you still had to get from A to B.

The end result was "don't check that box!" but any other box was ok even if it did the same thing or worse.

Yeah, that's another big problem. Rules are complex, but most companies in the space are taking a simple approach by defining static rules rather than ones built on top of market conditions that humans can easily reason about (eg "this non stop flight is $500 more, is it worth it? it's the only reasonable way to be awake during tomorrow's meeting"). It's all very broken, and we're hoping to solve it
I recently had a fun experience with something called the "Fly America Act", a law which says that when the US government is paying for your travel you have to fly on a US flagged airline.

For my trip, the flight would've been about 6 hours (direct!) and cost $600 on a foreign airline. On the cheapest US carrier, the flight was about $850 and took 10 hours due to a layover. When you take hourly rates into account, it easily cost the government an extra $1000 for me to travel on the US airline.

I wish I could've taken the direct foreign flight and just sent United a check for $250. Would've been a win/win for everyone— the American airline gets its corporate welfare without any of the costs they incur when someone actually gets on their plane, and I wouldn't have had to waste 4 hours of my life each way sitting in an airport to satisfy a dumb law.

The Fly America Act is pork for the Airline industry; they aren't intended to save the taxpayer money. Exactly the opposite.

I've even seen identical itineraries -- one under a US flag carrier and the other under a foreign flag -- with a mid-3-figure price difference. The airlines know what they are doing.

Call your congresspeople.

Don't you think it was policy so they can capture the information and get reporting?
Oh I have no doubt.

I write some software that involves accounting. Surprising how they drive A LOT of things. Sometimes a bit too much...

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Kickbacks, plain and simple.

For example:

My firm requires we use a corp booking engine. That engine charges a fee to book a ticket online or over the phone. We get a slight discount on fares and they in turn give a kickback each year to my employer.

The real kicker is that they sell some fares as "refundable" when in reality the fares are just regular fares but allow rebooking via this corporate travel agent. They've essentially locked you into using them and any interaction with an agent incurs a fee. My firm doesn't care, they just see that kickback at the end of the year and are happy. They don't care how inconvenient it is to use the TA.

I get some of the desires to control costs but in my case, I have schedules to keep and a lot of last minute travel and the corporate TA is nothing but an inconvenience. I frequently have to put in reasons for "breaking" policy (for example, I don't take red-eyes) on price because the limit between the lowest fare and your ticket is $100. So if the schedule is right but the fare for that is $110, you have to put in a reason why you booked it.

Can it take into account climate changes as well? And reduce/optimize travels, favor train, ..
Yes. We have "customer personas" that we bucket companies into and allow custom rules on top of that... though we don't believe they're usually actually necessary.

Do you wanna use Carry at work? Happy to talk to you / employer.

Hi HN! We've been impressed with the response here. Y'all must love travel.

If you use Slack and want to get started using Carry for your team, we've created a temporary link while we're on the front page to go ahead and install Carry. Here's the flow:

- Go to https://carry.travel/hnpromo

- Select your team's workspace in the top right

- For "Post to", select "Slackbot" or anything (this step is annoying, sorry-- we'll fix)

- Click "Install" (You may have to ask an administrator depending on your settings)

- Send a _direct message_ to @Carry on Slack saying anything

If your team uses another platform or wants to get in touch, schedule a demo (under the request access button, https://carry.travel/) or email tejas [at] carry [dot] travel, and we'll be in touch.

This reminds me of Magic (https://magic.gd) or Fin (now defunct, https://fin.com - a closer match, with a similar if broader mission).

Hopefully the narrower scope will allow you to escape the issues that Fin ran into, trying to bolster their team. :)

Magic has fixed pricing for some tasks, including travel booking I believe - so hopefully Carry is (or becomes) either less expensive or higher quality.

Is this the same Magic?

https://getmagic.com/

Yes, that's the same Magic. I think https://getmagic.com is their main URL, but I have magic.gd in muscle memory since it's shorter. :P
For some reason I get 502 Bad Gateway when clicking your magic.gd link but entering magic.gd manually works.
We too are hopeful that the narrower scope will allow our economics to work out!
> We found that no one actually wants to use these tools— they just have to, and that the only people who were satisfied with the state of things were folks who had assistants they could offload the work onto.

I suspect this is the case with a lot of business / enterprise software.

Congrats on the launch. I think this space (software assisted services that rely on Slack / SMS / email) is a promising one. Best of luck!

I wonder why enterprise tools end up this way, is it because the buyer (CFO/procurement) is different from the end user (employees)?
That and also distribution. One of the hardest part of breaking into enterprise is selling, and once big companies have a sales motion in place and locked-in customers (both in data on their platform and internal processes), penetrating crappier products into the market is increasingly easier so the quality bar goes down to some extent.
I was in b2b software sales until recently. I've been on the other side of the table when the buyer will be an end user, or when they have end users they're placing trust in and actually listening to.

Imo the issue is more just that ease of use is a hard sell. Buyers, including end users, want features. Lots of them. They want to be able to do everything they could ever potentially think to do within your software, doesn't matter if some of those tasks are once a month/year items for which perfectly good solutions already exist and for which there's no real gain from having it within this solution. It's what they ask about, what they want to talk about, what they test for, what I get feedback on from them when I win/lose the sale.

They might want ease of use in 6 months when they're actually using the thing and not give two hoots about most of the things they were certain were necessary earlier, but that's irrelevant. They didn't want it when it mattered. Now they're locked in. In terms of contract but also in terms of what their processes are designed for, what their staff are trained to use, what their other tools integrate with; and there's no guarantee or even reason to believe that an alternative wont be just as bad.

So there's tons of pressure on b2b software providers to do a lot of things but very little to do any of it well.

This is exactly it. You don’t lose an RFP if your product sucks. You lose an RFP if you say that it doesn’t match one of the 700 outrageous requirements
Do you use affiliate programs to get a cut of any bookings you make on your customers behalf?
Interesting... How are you performing the bookings? Are you registered as a travel agent with GDS access? Or are you going through an other agency?
We're partnered with a travel agency with GDS access. Additionally, we use various other OTAs that give us the full range of inventory for hotels and flights.

In general, travel agents that only use GDS don't have access to budget airlines such as Easyjet or alternative accommodations such as Airbnb or Sonder.

Ok makes sense. So you’re acting as a TMC but without the TA part? I guess the difficulty here is incident support: Say I’ve missed a flight and I need to be rebooked, hotel and taxi notified etc... With a classic TMC I call them on the 24/7 hotline and some agent will do it live for me. In your case the support line would be you right? Because your travel agency might not have access to the airbnb reservations etc. But then isn’t it tricky to intermediate the rebooking discussions between the customer and the agency?

Extra question: how do you manage the non-gds content? Do you ask your travel agency to add remarks to the PNR, or have you built your own database to track these “PNR+extra” bookings?

Sorry, lots of questions but it’s a really interesting idea!

We do the TA part, too. We book flights, hotels, Airbnbs, cars, etc. so we can reschedule everything in incidents, not just one part if customers use us full-service.

And yeah, we have our own database for everything. GDS is just one way to book and a "portal to the airlines" for us

How will you handle itinerary changes by the airline?

I know lots of people regret booking with Expedia or the like when there’s a change and they can’t deal with the airline directly.

There might be some value in doing EU261 claims and their equivalents on behalf of businesses. My guess is that nobody pushes the claim when the employer is paying the bill.

Founder here. Currently, you have to go through us to make changes to the reservation or respond to airline itinerary changes, but we have an emergency line 24/7 (think PagerDuty), and we believe we can do a much better job of dealing with the airlines than individuals (and optionally over chat instead of phone calls!). There's actually a lot of things you can do to manage reservations for customers on the backend that are not utilized in sites like Expedia that travel agents do (eg on this DOS-like terminal for the "GDS", you can manage reservations in the same backend that the airlines use).

> There might be some value in doing EU261 claims and their equivalents on behalf of businesses. My guess is that nobody pushes the claim when the employer is paying the bill.

This is a great idea. I actually haven't thought about doing this. I actually had a super delayed flight back in the day

Just to clarify: There are already services for consumers that will take care of EU261 claims on your behalf so you don't have to force the airline in court (and possibly you would just contract for them), but, like I said, for a corporate-paid ticket, I don't think anybody bothers.