The Tool Saving You $$$ On Flights, Even After They're Booked

Plus, our giveaway winner and a dreamy travel-related job I stumbled upon.

Hello again! Tomorrow, I’m embarking on a trip I would’ve never gotten without this community. More to come but in the meantime, grateful is an understatement.

(Relatedly, for our paid subscribers, our giveaway winner is… Elizabeth R. You’ve won $50 to the airline of your choice, in honor of this week’s theme. DM me!)

I was skimming LinkedIn the other day, as one does, when I came across a travel journalist post about a tool that saved him $210 on a flight he’d booked. Since I fly 10+ times a year, my eyes locked in: What stood out to me most wasn’t the amount (though I’d love to $200+ back in my pocket), but that the process seemed entirely passive—he didn’t have to do the ol’ rigamarole of cancelling and rebooking.

The tool in question? Sky Key.

Sky Key monitors your booked flights and grabs the lowest price if they drop—and about 50% of flights drop, with savings of ~$120 on average, according to their team. It even works on flights redeemed with points. The savings come back to you as future flight credits or refunds, depending on your ticket, and your flight details never change. (Remember what I said about the hassle of having to cancel and rebook?) If Sky Key saves you money, they charge 25% of the value once the flight departs—an intentional decision on the team’s part to wait since prices drop until departure.

Immediately after signing up for my own account, I reached out to the founder, Jacob Goldberg, to learn more. Within a few hours, he had sent along information as well as set up time to chat directly. This might not seem particularly impressive, but for a founder to take time to connect with a travel writer and position it as essentially, “We always find women are our most loyal users, and we’d welcome any chance to get to know our advocates” really stuck with me. For transparency’s sake, the link is a referral link, but this post is not sponsored in any way.

As Jacob puts it below, if you travel by plane more than once a year, then Sky Key is likely worthwhile for you. For what it’s worth (from my POV), it’s entirely free until you get money back, so it feels like a no-brainer. I asked Jacob questions below about Sky Key’s features, safety, and AI, but if you’re still curious, you can learn more on how it works and their FAQs.

Sign up for Sky Key here. Happy flying (and saving your hard-earned dollars along the way)! 🛫

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All About Sky Key: Saving You $$$ on Flights

Jacob, thanks for joining me for an interview. Departure is a weekly Substack focused on travel for women, and many of our members are active flyers, so I think this tool can be really useful for them. Can you share the impetus for developing Sky Key?

The impetus for developing Sky Key came out of my own experience and frustration with booking flights. A couple of years ago, I noticed I had two flights that were selling for less than what I originally paid for them. When I saw that, I canceled and rebooked them for the cheaper fare. In return I got future flight credits, which are as good as cash to me because I travel a ton.

I immediately had my “aha” moment and realized that the majority of people weren’t paying attention to what happens to the price of their flights after booking. Most other websites and platforms in the travel space are focused on search, whether that be trying to find deals ahead of your trip, trying to predict when the cheapest time to buy your flight is, or ways to optimize points and miles. I quickly realized with my own travel that, by just ensuring that I pay the cheapest price for every flight, I was saving way more money than doing all of those other things.

While I discovered the idea for Sky Key by cancelling and rebooking my ticket, we actually don’t do that for customers. We were able to build the technology such that they get the same benefit without cancelling and rebooking. Flight details always stay the same, and nothing gets canceled.

Thankfully, my now co-founder, Billy Bund, is a tech genius who was able to help bring this idea to life. There are essentially no other other goods or services we buy that fluctuate more in price than airfare. In other words, you don’t go into a grocery store one week and buy blueberries for $4.99 only to see them go to $11.99 the next week and then back to $4.99 the week after that.

Why do consumers today accept and not think about the fact that the price of their airfare might drop by 25% or 50% the day after they book their flight? Sky Key is changing that.

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Your business model is such that you only make money if the customer gets money back, so 25% of savings are sent to you. I’ve seen other organizations work this way, specifically around healthcare bills, where they’ll fight to lower your bills and they take a cut only if they win. Can you share how you landed on this business model, and how it’s going? What have been the biggest wins?

As an example, if we get you a $100 future flight credit after the price of your flight drops, you will actually get the full $100 from the airline. We will charge you $25 [via credit card] when your flight departs. We often see multiple savings happen days, weeks, or months apart on the same flight, which is why we do it that way.

The reason we landed on this model was because I always felt like we should only make money if we make you money. Our whole business revolves around trying to save you money. Why should we make money for just trying? If we deliver, both you and I win. If you don’t save money, you don’t pay anything. Easy to understand and very aligned with our customers, and this resonates very well.

The record is 17 price drops and savings on one flight. The biggest wins come on international first class tickets where we save customers thousands of dollars frequently, and the record savings amount for a single customer flight is $4,684. We also work with businesses and have saved some of them multiple five figures on employee travel.

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When I first heard about Sky Key, I was under the impression it was for cash flights only. That is to say, I didn’t think it’d work for flights redeemed with points, but it does! You value your points at 1,000 points = $10 in value, so if you find a drop in price for 10,000 points less, the customer would get $100 back to them. Is that sent back to them as a credit with the airline?

Yes, Sky Key also works with points. When we save you points, the points go back to the airline account that they were booked from. We assume a 1 cent per point value on any points we save you, so in your example: If we save you 10,000 points, you would get 10,000 points back and then would be charged $25 for that.

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You have a fun calculator on your site where you can input your annual costs of flights, and it’ll show you projected annual savings by using Sky Key. Is it safe to say that this works better if you’re a frequent traveler?

The more you travel the more you save. If you travel more than 1x per year, Sky Key is worth it. It is worth noting: Most flight credits expire after either a year from when they are issued or a year from the original flight booking date. It’s definitely something to pay attention to, and we provide that relevant information to our customers.

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I do think it’s also worth mentioning the caveat that this doesn’t work with Basic Economy purchases given their restrictions. Are there any other use cases customers should watch out for (i.e., flights booked with both cash and points, airlines you don’t work with yet)?

100% worth mentioning that it doesn’t work with Basic Economy tickets. Airlines do not allow for price matches or adjustments to Basic Economy tickets, which is why we don’t support those.

However, I always tell people: If paying the lowest price is your #1 constraint, you should compare the cost between Basic and Main when booking. If that difference is within $50–$60 you will save more money over the long run by booking Main and using Sky Key than booking Basic. We often see Main tickets drop below the Basic fares people are paying for the same ticket. And Main/Regular Economy fares offer a few extra benefits, like selecting your seat. Don’t get stuck with Basic!

Other things to look out for are as follows:

• Always book directly through the airline, not 3rd party OTAs or travel portals like Expedia, Orbitz, Chase, AmEx. You will get cheaper fares and be able to use Sky Key to your advantage. It’s also easier to manage your flights if something happens or an unexpected travel disruption arises. Booking through credit card travel portals is generally a terrible value for your points. Please don’t waste your points like this!

• Don’t book a combo of money + miles. You’ll get a bad redemption rate for your miles if you do this (usually 1 cent per point) while your miles are worth more than that if used on their own! Also, money and miles combo tickets are very rare to get savings with Sky Key.

• We do support international airlines if they’re booked through the US carriers we support. For example, if you book Lufthansa on United—or AirFrance through Delta—we support those! [An editor’s note: So far Sky Key works on the five major US airlines, hence this callout.]

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Let’s address the elephant in the room: Sky Key is made possible by AI. Are you supporting any initiatives or building other processes in the backend to minimize the carbon footprint made by both AI use and travel?

It’s not a secret that Large Language Models (LLMs) like ChatGPT consume a tremendous amount of energy. With these models, the more you use them, the more energy you consume, and the higher your bill.

When my co-founder and I started Sky Key two years ago, we were paying all of the bills out of our own pocket so we needed to keep our costs as low as possible. Because AI is a major part of Sky Key’s infrastructure, we needed to keep our AI costs to a minimum. So we spent countless hours optimizing how we use it to make sure we were keeping costs/energy usage as low as possible. Even as Sky Key has grown immensely, we continue to use AI very efficiently.

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For anyone curious about security: You require a credit card on file and you access emails and personal flight data. You did say you use Stripe for processing, but do you have other security features to protect users’ data?

Great question. Sky Key encrypts user data at rest and in transit. All data collected through email sync is stored in a secure cloud environment and protected by AES-256 encryption. Additionally, a third-party security audit is performed annually for Gmail Sync customers.

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What’s next for Sky Key?

Right now, we are very focused on scaling the current product and delivering the best possible customer experience. I want every single customer who signs up for Sky Key to have their “aha” moment, just as I had mine years ago which led me to build the product. I am passionate about helping people save money on travel so they can travel to more places and create more memorable life experiences. In order to effectively do this for millions of customers, we have to be very focused and not get distracted by bright shiny objects—easier said than done ;)!

Truthfully, it’s really hard to build great products that solve real problems and deliver what they say they’re going to. We take great pride in the fact that we are the trusted market leader in our space and bring a great value to consumers, while also driving repeat business and increased customer engagement for the airlines we support.

There is a lot on the roadmap and we will add adjacent products and services down the road where we see the best fit for our customers. Both myself and my team think we are just scratching the surface with what we are doing today and we’re excited for our customers to follow us along on the journey.

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I laughed at your FAQ that said Sky Key is, in fact, gluten free. Vegan, too?

Haha, sure thing! We love Sky Key’s personality :).

• 📺 We recently started watching Task on HBO Max, starring Mark Ruffalo. The first episode is a slow burn, but five episodes in and we’re hooked (season one will be seven episodes). A great watch to download for your next long-haul flight.

• 📚 Cozy horror books to read this fall. Can you use “cozy” and “horror” in the same sentence? (Penguin Random House)

• 🐕 The best dog-friendly beaches across the country. I knew this list was legit when my favorite beach in Santa Barbara made the cut. (US News)

• 👀 Skift is hiring a Membership and Engagement Manager for its “Women Leading Travel” vertical. Remote in the US, up to $75k.

• 🇦🇷 Adding the librerias de Buenos Aires onto my bucket list. (h/t Patricia Audibert | Dogma 95)

Wishing everyone a quintessentially fall weekend, full of (early) foliage, pumpkin bread, and warm lattes. x —Henah

weekend mood inspired by monet // credit