Talking Points Episode 22: Everything You Ever Wanted to Know About Working at TPG, From the Boss Himself

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Brian Kelly: Hey, Talking Points listeners, it’s your host Brian Kelly, The Points Guy. As you know, Talking Points is a podcast where I sit down with CEOs, top executives, influencers, TPG staff and other interesting people to talk all things travel. On this episode, I’m sitting down with two of TPG’s finest employees, Kate O’Brien, our Director of Business Development, and Scott Mayerowitz, our executive news editor. We’re gonna get into TPG’s evolution as a company, how we’ve grown and continued to expand, and how you our listener could be our next employee. Listen all the way to the end because Kate and Scott are gonna be giving out some details on some pretty cool positions at TPG, and the dos and don’ts of interviewing here. Hint, don’t use a debit card.

Brian Kelly: Our first guest today is our longest standing full-time employee, Kate O’Brien, director of business development. Kate, thank you for joining us.

Kate O’Brien: Thanks for having me.

Brian Kelly: Not that you really had an option because I made you do this. Kate, you started out at the company right out of college. You started in a very illustrious role.

Kate O’Brien: I did. I was enjoying my last summer working in the Hamptons right after I graduated and you gave me a call asking to be your assistant. For some reason I said yes.

Brian Kelly: I don’t even want to ask you how it was being my assistant seven years ago. How many employees were we then?

Kate O’Brien: We were three, so I was employee number three.

Brian Kelly: Who was number two?

Kate O’Brien: Eric Rosen.

Brian Kelly: Oh, Eric Rosen. Correct.

Kate O’Brien: Yes. Writing a lot of your posts at the time.

Brian Kelly: Our posts. It’s a collective effort. But anyway, you came in as my assistant. You quickly grew throughout the company. You started managing all of our compliance and making sure that blog posts were up to date because-

Kate O’Brien: We can get in a lot of trouble.

Brian Kelly: Yes, and credit cards are how we make money here at The Points Guy. You’ve basically been managing all of our relationships with the credit card issuers. What is that like on a day-to-day basis?

Kate O’Brien: Yeah, so it’s a lot of check-ins with them, usually bi-weekly and monthly. We are going over performance for the month. Any upcoming initiatives, product offer changes. I usually get let in on the exciting news early and I can share it with our team so we can put together a full marketing plan.

Brian Kelly: How would you say our relationship with all the credit card companies has changed over the years?

Kate O’Brien: I think it is so much closer than it used to be just because we’re actually giving them a lot of data back, and sharing our performance, and making sure we’re both working together so it’s much more a partnership than just being a straight affiliate. We’re really helping them kind of pull together their whole campaign so we can help them market on our site.

Brian Kelly: I think one of the biggest moments in The Points Guy evolution was in 2016 when Chase came to us with this secret new launch, and you really helped spearhead that program which ended up being the Chase Sapphire Reserve which obviously was a huge success. Now, what was that like working with Chase behind the scenes on that [crosstalk 00:03:02]-

Kate O’Brien: It was stressful, but it was exciting. They had come to us a few months in advance, and they asked us to sign NDAs, and they even told us make up a fake product, and tell us how you would market it on your site. We made up the Sapphire Gold Card, I think we called it, and mocked up some site skins and ad placements. Then, throughout the next couple months, we really worked with them really closely on building out ads and making sure everything was legally approved which takes a lot of time. But being able to launch that with them was probably the highlight of my career, I think, so far.

Brian Kelly: Yeah, because there were no other blog partners. There were a couple of other sites that had that product at launch, but we were the only blog to carry it. Ostensibly, the best credit card to ever hit the market. 100,000 point bonus. I remember I was actually in Tanzania. You guys had gone to Chase in Delaware and got the official details. I remember I was in a tent in the middle of the Serengeti with terrible internet connection, and I think you said, “Brian, you’re gonna want to sit down for this one.” I-

Kate O’Brien: Did it live up to your expectations?

Brian Kelly: I would say so. The card going viral, them running out of metal, and us really partnering with them in ways that we had never done before was really cool. Plus hundreds of thousands of our readers getting excited to get such an incredible deal. That was a really cool moment and that got so many new points people in the game. Traffic continued to grow. 2017 came, people thought Chase Sapphire, are you guys just all Chase? Is there competition when you’re talking to the other issuers?

Kate O’Brien: Of course it’s competition, but I think that they’re all just wanting to get their products out there and make sure they’re doing it in the best way possible. It helps for them to see what we’re doing with other issuers because that makes them want to get in on us, too, and be a part of it.

Brian Kelly: What do you say when people say, “Oh, The Points Guy. You’re getting paid by the credit card companies.” Are they paying for the reviews and to get … Do the issuers come to you and say, “Hey, look, we’ll pay you more if you guys give us a favorable review?”

Kate O’Brien: No. I think they really value that we give our honest opinions of products, and they know that they would rather us talk about a product honestly, and really weigh all the benefits out. People trust us and they’re gonna take our recommendation seriously when we say a product is really good and worth getting.

Brian Kelly: The whole thing is our readers are smart. We can’t run one over on our readers. We drive the value prop through the points valuations and our team of points nerds. Explain who’s on your team now, and the roles that you’re looking for.

Kate O’Brien: Yup. I have Jake on my team now who actually came from Citibank. He was on the investor relations side, and he is really helping build out our TPG partner program. We’re working with other media sites to write about credit card content, and we give them a share back of the revenue there. Jake is really helping with that and just kind of build(ing) out new revenue opportunities for us. Then, we are also looking to hire a business development analyst, ideally with one to three years of experience, really can excel at reporting, SQL, and just really help us with the day to day task of getting performance.

Brian Kelly: Do you think I would be good at that role?

Kate O’Brien: Reporting? No. Do you know how to make a pivot table?

Brian Kelly: What is that?

Kate O’Brien: What’s that?

Brian Kelly: No. I used to do that when I was a buyer at Lord and Taylor. I was an Excel … Actually, no I was not an Excel. They quickly moved me into HR because I’m more of a people person which is fine. We all have our strengths and weaknesses. When you interview people, what are you looking for?

Kate O’Brien: Affiliate experience is important. Being able to understand conversion rate, and kind of the funnel metrics, and just really modeling out different revenue opportunities as we’re trying to diversify our revenue a bit and get into new spaces and partnerships with airlines, and hotels, and tour agencies … but we just can’t say yes to everything, so we have to make sure it’s gonna be worth our time.

Brian Kelly: What is your favorite part about working at TPG?

Kate O’Brien: I love that I am on the revenue side of the business, so we’re working on really big package deals that are really exciting, and I get to kind of craft different packages for the issuers and get let in on early about their new products and limited time offers that are coming out. It’s really always changing. Every month there’s something different to work on. Even every week it’s something fresh. Never gets stale. There’s always something to do.

Brian Kelly: You’ve been here for seven years. You’ve seen the peaks, and valleys and offers. What is your overall outlook? Obviously, you can’t tell us any deals coming down the pike, but do you think 2019’s gonna be … the rest of the year is gonna be a good year for bonuses and new card launches?

Kate O’Brien: We have heard some rumblings of some excitement towards the end of the year with some new products coming out, and I think our readers will be very interested in them. But that’s all I’ll say.

Brian Kelly: I don’t know. Tell me. Come on.

Kate O’Brien: Can’t.

Brian Kelly: Kate, what fun travel do you have coming up?

Kate O’Brien: We are planning a trip to Japan for our one year anniversary this summer.

Brian Kelly: How are you gonna fly there?

Kate O’Brien: We are taking United Polaris Business, and then we’re trying to [crosstalk 00:07:53] find-

Brian Kelly: Did you get save rewards?

Kate O’Brien: We did. 80,000-

Brian Kelly: From [Norita 00:07:57]?

Kate O’Brien: Yes, and we’re trying to find Japan airlines first class for the way home.

Brian Kelly: Using Alaska 70K each.

Kate O’Brien: Yes. Ideally, but I’m told they’re very hard to find.

Brian Kelly: Cool. Kate, thank you for joining us, and safe travels.

Brian Kelly: All right. Now, we’re gonna take a quick pause to hear from our sponsors.

Brian Kelly: All right, our next guest up is a relatively new hire to The Points Guy. I’ve known him for years. I had actually tried several times to get him to work at The Points Guy and he politely declined. Declined, but I, if anything, am a relentless person. Finally, he joined as our executive news editor: Scott Mayerowitz.

Scott Mayerowitz: Persistent is a very good word to describe that process.

Brian Kelly: Did I get your last name right?

Scott Mayerowitz: You did.

Brian Kelly: Can you say it for the record?

Scott Mayerowitz: Mayerowitz. Scott Mayerowitz.

Brian Kelly: Scott joins us from the Associated Press if you’ve ever heard of them.

Scott Mayerowitz: Small little news organization.

Brian Kelly: Has been in media for years, and now is running the day-to-day editorial operation at The Points Guy. Scott, what is a typical day like for you at TPG?

Scott Mayerowitz: Typical day? There is no typical day. As any traveler will know, it’s just crazy in the news world. I usually get up around six o’clock. I check in on any breaking news that happened. One of the great things about TPG is, as we’re growing, we now have people positioned around the clock. If I see something at six o’clock, I can reach out to the team in London and say, “Hey guys, can you help us out with it?” I kind of do a quick spot check then. We get our morning meeting where we talk about all the news that we’ve got lined up, and we kind of all just sit around brainstorming. Talk about what’s going on. Then, we launch through the day. That’s when I’m in the office.

Scott Mayerowitz: When I’m out of the office, I’m … I’ve been here now four months. I’ve met with all the executives at the four major US airlines. I’m meeting with Wall Street analysts and other folks. I’m doing a little bit as a reporter, little bit as an editor, and hiring, hiring, hiring. There is no typical day here.

Brian Kelly: We write between, in a normal day, 25 to 30 posts. How much of that is preplanned, and how much content every day is generated that day?

Scott Mayerowitz: Our goal is always to have at least half of that content planned out in advance. Some of the stuff that you can figure out like family travel, all that we’re planning out two, three, four weeks in advance, and we’re saying, “Hey, Memorial Day, July 4th, Labor Day, Thanksgiving, Christmas. What do you need to know now for all of those holidays?” That’s quick. A lot of the deals, the frequent flier changes, that happens during the day. We can easily have 15 posts that we don’t know about when we wake up that by the end of the day we’re creating. Even in our morning meeting, things drastically change by two or three o’clock in the afternoon.

Brian Kelly: It’s funny, people always ask me, “Oh, the airlines must hate you.”

Scott Mayerowitz: It’s very funny because I was just down in Atlanta meeting with a certain airline the other day. You can guess who, and if you can’t-

Brian Kelly: AirTran.

Scott Mayerowitz: … you probably shouldn’t be listening. I actually saw some of those AirTran hangers still around. I was down with Delta, and I was amazed at just how excited they were to talk about our growth, and where we’re going, and what we’re doing, and how engaged the airline executives were, and really knew down to the details about some of the posts that we had. It’s one of those things where I think the airlines really do love us. We’re not out to get them in any way, we’re out to educate people on how to be smarter travelers. At the end of the day, as I was saying down at the SkyMiles folks, we were talking about some of those ridiculous 500, 600,000 mile rewards that you’re like, “Oh my God, what the heck is that?” But they’re like, “Hey guys. A lot of people are redeeming for 12,000 mile one-way domestic trips or 5,000 mile super saver things. There’s value there, and you’re educating people about, yeah, the weaknesses in our program, but also the really cool things.”

Brian Kelly: Editorially, you’ve been here since January. Where do you see our gaps? We’re gonna get into hiring and some of the strategic roles. How do those roles that you want to hire play into where we want to take our editorial?

Scott Mayerowitz: I think one of the things that you and I have talked about a lot is we’re really good at covering aviation stuff, but getting into original reporting on really wonky stuff and bringing that back to the consumer. I don’t want to give away any secrets here, but one of the great things we do is we travel a lot. What are those big projects where we can take all of our people and maybe say to them, “Hey, do you want to stop by for a half an hour of this thing related to your trip and enter a few data points for us?” If we have 40 or 50 data points, we can have something that’s really original.

Brian Kelly: Our quarterly reports — we do best airlines, best airports. What are some other ones that people can expect coming in 2019?

Scott Mayerowitz: Yeah. I think one of those things that you want to really look at are some of those decisions about what aircraft type should I be taking. Again, not to give away too much, but I think domestic fliers are going to really want to know what are some statistics around the A321 versus maybe a Boeing 737, and which airline, which hub has some delays. We’ve got some interesting things up our sleeve that we’re working on.

Brian Kelly: You’ve piqued my interest. I don’t even get told these cool things anymore. I’m so out of the loop. No one tells me the fun stuff. You’ve been a point maximizer. What are the top three cards that you use mostly?

Scott Mayerowitz: Well, it depends. Am I keeping that card in my wallet for the benefits? My Amex Platinum I will charge some airfare on, but I really like some of the other elite benefits that come with that card. I still am a Chase Sapphire Reserve fan for certain things, particularly the trip delay insurance. I will be back and forth, depending on my trip, on booking airfare between that and the Platinum card, depending on how likely I think there might be something where I need insurance for.

Brian Kelly: Yeah, because that Reserve’s got up to 10,000. I know during the WOW Air debacle, people who use Reserve could just book hotels and then just submit for reimbursement. Whereas, Platinum gets 5X on points, but there’s no trip canceling.

Scott Mayerowitz: Exactly.

Brian Kelly: You might be able to get a refund of the charge but they’re not covering hotels and new flights and all of that.

Scott Mayerowitz: Yeah. Then, I am a Delta Elite person, and boy, I get a lot of pushback from people in the community for this. I actually put a lot of spend on my Delta Amex. As you know, SkyMiles are not a preferred redemption, but you can charge your way to elite status. I have a 4-year-old at home. I’m not traveling as much as I should. I actually looked at my flights for the year, my average stage length or distance flown is 821 miles. I’m doing a lot of short hops.

Brian Kelly: Florida, Atlanta …

Scott Mayerowitz: Florida, Atlanta, Charlotte. For me, the Delta Amex is a way for me to get that next year of status. I have the Reserve card and the Platinum card and the Small Business Reserve card.

Brian Kelly: Now, let’s talk about the open roles in your organization, and maybe some that are coming later in the year that people can be looking out for, and what you look for in a ideal employee.

Scott Mayerowitz: Yeah. Let’s start with the ideal employee. I want someone who has those credit cards in their wallet, and has that points and miles expertise. I’m gonna geek out here for a second. We were talking about pivot tables at one point today. I have Excel spreadsheets for all my frequent flier points. Expiration date policies for my entire family actually. And I keep track of all of this. I wish someone would create an easier way to really track all my family’s expiration points and some of the quirky things like companion certificates when they expire.

Brian Kelly: I think that new TPG app that’s in the works may-

Scott Mayerowitz: May solve that problem.

Brian Kelly: May solve some of those issues.

Scott Mayerowitz: That would be great. I want someone with that expertise and someone who’s traveled, whether it’s scraping together 40 bucks for a bus ride to go somewhere cool, or spending 10 grand or a lot of miles for a really great trip. But I also want someone who can write and understand some of the rules of what you should be asking, how to press for more information and how to really develop sources because we are going to expand our ability to be the first out there to report on things and to make sure that … We’re already the top source for everyone to come to, but we’re not first on everything, and we need to be and will be by the end of the year.

Brian Kelly: Now, one of the things we always struggle with is traditional journalist/amazing writer versus there’s not tons of amazing journalists with deep miles and points knowledge. Arguably, our number one producer, writer extraordinaire JT [Genter 00:17:13] wasn’t a writer, and he was a CPA and a reader for years. Very avid reader, and then I think he kind of broke me down, and I was like finally, “Let this guy do a flight review.” He wanted to do Air China Economy and it went viral, and then he started writing more, and then we eventually offered him full-time. Now he is our star writer in many different metrics. How do assess, how do you balance that miles and points nerd knowledge versus writing ability?

Scott Mayerowitz: I think it’s like a salad bar. You have to go and you have to pick out a little bit of every skills, and JT is phenomenal. He is one of those amazing people who — I just like sitting down and chatting with him, actually. Forget his writing. He knows this stuff in and out.

Brian Kelly: His travel style. To him and his wife, who are global nomads, take these weird train rides in Mongolia. Their content is just fascinating. I would never want to do it, but it’s fun to read.

Scott Mayerowitz: That’s part of what we need is we need someone who’s gonna do these crazy train trips, and then we need someone who’s gonna stay at the Mandarin Oriental and do a review. [crosstalk 00:18:20] I’m volunteering-

Brian Kelly: I got it. I got it.

Scott Mayerowitz: Oh, your loss.

Brian Kelly: I’m not allowed to do reviews anymore because I’m the worst flight reviewer in the world because I’m chronically exhausted, and I get on and I sleep the whole flight, and I take one picture on my iPhone. Then, I’m in the office like, “Why aren’t these photos better? Oh wait, that’s my review.”

Scott Mayerowitz: Yeah. Someone asked me about-

Brian Kelly: The new kids these days.

Scott Mayerowitz: I flew business class over at Amsterdam the other month, and someone’s like, “How was the flight?” I’m like, “Honestly, taxi out was great, and I woke up for landing. I slept.”

Brian Kelly: Versus our reviewers now who have temperature gauges. JT’s there with his ruler measuring the tray size.

Scott Mayerowitz: Yeah. I think we need a mix. We need someone who’s gonna sit and look at data. As traditional media shrink, there’s no one at any of these newspapers who’s looking at Department of Transportation statistics and really digging through how many lost bags did American have this month, or how many wheelchairs did United break in the last month. These are all important topics that we can own at TPG. You need someone with that, and then you need someone who’s with a backpack traveling every weekend or whatever. We’re trying to bring that in and bring other voices who can help expand us to other markets.

Brian Kelly: Let’s get into some of the roles you have open now.

Scott Mayerowitz: Yeah. We’re looking for someone who’s just a points, miles and deals guru. Someone who can really break this down and is like, “Hey guys, 300 bucks to Vietnam. Book it now,” and really build up that. Because we’ve got some great people on staff for that, but we need more there. We’re also looking for another person to build out our aviation team. Ben Mutzabaugh, he’s heading up that team. Well, he needs some more people who are wonky data folks who can tell you what’s the best time to fly, or why you should connect in Charlotte instead of DFW if you’re flying American.

Scott Mayerowitz: We’re also gonna increase the folks who are looking into credit cards for us. There’s a lot to analyze on those benefits. Should you be using Chase Sapphire Reserve for flights, or the Amex Platinum, or the Venture Card or something like that. We just announced Benet Wilson is gonna be coming on.

Brian Kelly: Who is awesome. I’ve been following her for years, and so glad that she’s joining.

Scott Mayerowitz: She known as the aviation queen. She is one of those people who is just a wonky travel aviation person, but she also knows how to maximize credit cards, and she’s gonna help the great team that Sarah Silbert’s putting together there.

Scott Mayerowitz: Back to the time difference change. We’ve got the London office to help out, but there’s a lot of stuff that happens late at night and we want to be first on it. We’re gonna be hiring someone on the west coast who’s gonna really help with those late-day breaking news stories to make sure that when you wake up in the morning, TPG has that story for you. Then, just beefing up our weekend staff. That’s the other big area, again, because we’re all sitting there on weekends searching for flights. I’m sitting down with my wife and going, “Hey, when are we going again away for Thanksgiving? How do we book those flights?” We need to make sure that we’re staffed there. That’s our immediate hiring plan.

Brian Kelly: What’s something someone shouldn’t do when interviewing for an editorial role at The Points Guy?

Scott Mayerowitz: Besides telling me that you used your debit card to pay for lunch or that you pay in cash?

Brian Kelly: Yeah.

Scott Mayerowitz: The passion for travel. Everyone here has a passion and wants to empower people to travel. It’s really not just about staying at the best hotels and eating at the best restaurants. I think at the end of the day, we all want those trips. I want someone who has that passion, has that understanding and really knows that it is a privilege to travel, and this is not something that everyone can do every week.

Brian Kelly: Very well said. Scott, I know you just went to the illustrious Nickelodeon Resort. Do you have any other fun travel coming up this summer?

Scott Mayerowitz: My wife and I are heading to Grand Cayman for an adults-only fifth anniversary celebration.

Brian Kelly: Congratulations. [crosstalk 00:22:29] I love Grand Cayman. That was the first place I went in 1996 on points. Scott, thank you for joining us. Our list of jobs is constantly changing. We’ve got other divisions that are hiring as well. Specifically, if you are an app developer, computer scientist we are hiring in our Austin office to help on our app that’s gonna be changing the game coming out later this year, so visit ThePointsGuy.com/jobs to apply for any of these roles. Even if none suit you, follow us on social media, engage with us, come to our events, get on our radar and you never know. We love hiring our best readers/podcast listeners. Kate and Scott, thank you so much for joining us.

Scott Mayerowitz: Thank you.

Kate O’Brien: Thank you.

Brian Kelly: Again, I’m your host Brian Kelly, and this episode was produced by Margaret Kelley and Caroline Schagrin with editing by Ryan Gabos. Our theme music is by Breakmaster Cylinder. Special thanks to Christie Matsui, my legendary assistant. If you’ve been enjoying Talking Points so far, thank you. Please leave us a good review on Apple podcasts, Spotify, or wherever you get your podcasts. This episode may feature offers that are subject to change, and are offered by our advertising partners. ThePointsGuy.com is a free website, so we do advertise in order to generate revenue. For a full listing of our advertising policy, go to ThePointsGuy.com/advertising.

Featured Image by Natalie Roe/TPG