8 mins read

Skift’s Jason Clampet: How the B2B travel brand’s events paywall have subscribers dipping in for more

Four years after the global lockdown, B2B travel brand Skift is thriving thanks to its high-quality niche content, technologically-driven innovation and intelligent subscription protocols. Jason Clampet, the company’s chief product officer, tells Ashley Norris that agility and flexibility are key to a successful B2B media business.

  • Experimentation is at the core of the company’s DNA.
  • Offering a suite of free products is a surefire way to drive paid-for subscriptions.
  • Engagement is key to ensuring low rates of churn.

* Jason will be at Mx3 Barcelona on March 12-13, sharing insights in a session called “Subscriptions transformed: How Skift builds highly successful segment-orientated subscriptions offerings“. He will attend the whole event, so connect and meet with him there. The full Mx3 agenda is here. You can read more about the event here.

Tell me about your career. How did you end up at Skift? 

I was introduced to Rafat Ali, Skift’s CEO, by a mutual friend. We had a similar problem. I was working in consumer travel media, and he was looking to do his next venture in travel media. And neither of us could access good news sources to enable us to do our jobs.

After one or two meetings, we knew exactly what the elevator pitch for Skift would be and went about putting it together. 

The traditional B2B publications in travel had been around for a long time and were very, very strong. At one point, Travel Weekly operated out of two floors in a tower in midtown Manhattan. Now they’re in suburban New Jersey by a car park, but back then Travel Weekly was a weekly publication that was almost 200 pages. They had been around for a long time, but they were still writing for travel agents. As we know, in 2011 the landscape had changed dramatically in terms of the power of travel agents. 

So the whole thing was, “How do we look at the industry from the perspective of somebody who works in the industry who needs to understand all the moving pieces?”

Skift is quite an entrepreneurial company. You are always experimenting with new formats and new niches. Why is this the case?

As with any company that doesn’t have a tonne of venture-backed money, we try hard and experiment. Take, for example, our Skift AI tool, Ask Skift. We saw what was happening in the fall of 2022 when they made some of the first announcements about OpenAI and ChatGPT, and thought, “Okay, this is going to change stuff. We’re not sure how, but let’s experiment because the companies we’re covering are experimenting.”

It helped us in a number of ways. Our journalists were able to speak to travel companies in a very knowledgeable way. So, when a company would say, “Our app lets you do XY and Z with AI”, they’d be like, “Well, from what I understand with our experience of AI …”. And so on.

We don’t use AI to write stories, but we look at how tools can improve our daily workflows. For instance, one of our publications is the Daily Lodging Report, which is focused on the hotel industry. For the newsletter, [well-known gaming and lodging industry analyst] Alan Woinski writes in a narrative fashion about rooms in the pipeline. We’re able to take what Alan has written for that one paragraph, plug it into ChatGPT, and say, “Break this down into tables”. Whereas we used to do that manually, and it would take 25 to 30 minutes, we do that with the tool, and it takes about two and a half minutes.

Then we have the tools we give to our readers. Ask Skift is great for discovering answers that search doesn’t help them with. Most of our readers’ questions are not, “Where is Expedia located?”. It is asking about the difference between Expedia and’s business models. In the past, that was not something a search tool on a website or a search engine could tell you clearly because it cuts across multiple stories. 

With our AI tool, we can look at our research reports, and 12 years of stories on Skift and our other sites. It can also access transcripts of events where CEOs have talked. It’s really enabled people to get deeper answers to their queries. If you’re a paid subscriber to our Skift Pro, Skift Research, the Daily Lodging Report or Airline Weekly, you get full access. If not, we cap it at three free queries.

What key new products have you launched in the last couple of years?

The biggest innovation in the last three years is building our own paywall. Crucially, our paywall is not just about content, but it’s also about events. And like other B2B companies, that usually means working with a third party, which takes a chunk of the money and doesn’t always integrate well with your own services. 

We wanted to build an experience with our users that seemed totally under Skift’s control. If you’re a subscriber and logged in, the system has all your information, so whether you are trying to attend a free or a paid event, it is all seamless. We’ve continued to integrate that since we launched the Skift Pro subscription product in July 2020. We have been tweaking it, too, such as adjusting the number of page views before you hit the paywall.

We have also borne in mind the changing nature of events. During the pandemic and immediately after, online events were key for us. In 2023, we decided to ditch the online event experience that was trying to mimic the live experience. We realised that if you’re attending online, you really want to see one or two CEOs. You’re not sitting there for the full day.

So, if you are a subscriber, you can just dip in and watch what you want to. If you are not a subscriber, we use it as a tool to funnel people into the system. You can either subscribe and get it all for free or pay a nominal charge and get in. It was not a revolution, rather, it was a slow evolution that took into account key learnings from the pandemic.

Being an entrepreneurial company is often both a blessing and a curse because you are trying lots of things and, inevitably, some things won’t work. How do you make the process as efficient as possible?

I’d like to say that it’s a highly scientific targeted thing where we have these deep thoughts and come back with incredible stuff, but usually, it’s somebody within the company, sometimes it’s Rafat (Ali), sometimes it’s me, sometimes it’s somebody on the editorial team or marketing team saying, “Hey, why don’t we try this?” or, “I saw somebody else do this”, and us just giving it a shot.

For example, one of our salespersons said, “We should do live translations for events, and we can hook up with this person”. So then we integrated a tool into our system that allows that. It’s really about being open to anything and not having a lot of red tape and knowing that there’s no real cost of failure because we’re not spending tens of thousands of dollars to try something new. 

I’d say Skift’s AI tool was the biggest expenditure we had in deciding to hire an additional person to help with it. But in most cases, innovation doesn’t really cost that much. We’re not building our own CMS or doing anything crazy with lasers. 

What is your subscription strategy? How does your sales funnel work?

Like a lot of publications, people start by getting in for free. We get them interested in the product, and sign them up to a free newsletter. Then, from the free newsletter, if they’re like, “Okay, I need more of this”, they become subscribers. I think that’s the way they see a series of stories that are really specific to them or what they need to solve a business problem, and then they stick with it. 

We have a number of speciality newsletters that come out once a week – online travel, tourism, artificial intelligence – where it might be two to five stories that are specific to the subject people sign up for, and we see a lot of those people convert because they need specific stories. 

Then, people find other content that interests them. So, if you’re in hotels, you care about tourism, marketing, new trends, and airlines, etc., because all these areas impact on your core business. 

The research product is for people who are often at the same companies but in higher strategic roles, who, for example, manage a development pipeline at a hotel or are in charge of the technology spend at Expedia or Airbnb or want to understand the difference between mid-size hotel chains. So, a company will buy multiple seats so that people across a decision-making chain have access to the research. 

There is often an overlap between Skift Pro and Skift Research subscribers because they need the daily news and deep analysis. 

What advice would you give other B2B media about subscription acquisition and churn?

I’d like to be better at churn than we are. But I think we do a relatively good job. I want to do more, but the key to churn is managing engagement. So, we’ve tried to think of different ways to make sure that people are engaged. If we’re having a problem with email deliverability, we’ll do something like create a Slack distribution mechanism. 

For example, with one of our large enterprise clients, we kept hitting issues with IP addresses, and the content they wanted wasn’t coming through. So we created a Slack bot for them and they get their research in Slack whenever it’s released. So we don’t have to send them an email all the time. That helps with churn because then everybody’s engaged. 

We also try to make sure people are reading our stuff. That’s the main thing. What helps with churn is that while we offer discounts from time to time, we don’t do the dollar deal, the one month for $1, because those people are going to churn.

I know if I get a $1 subscription from The Athletic or The Washington Post, I’m going to let it lapse, and then they’re going to give me that dollar six weeks later. 

I’d rather have one $365 subscriber than 365 $1 subscribers.

We are almost four years to the month when the world went into lockdown. This was a disaster for the travel industry, but what was impressive was the ingenuity with which businesses kept going. What did Skift learn from that time?

In February 2020, we were getting ready to launch our paywall. Yet within a month we had shut our office doors, never to return. Everything changed. We had a business focused on travel, a third of which was in live events. So there was a bit of an impact on our business. 

Everybody who had signed on for live events said, “Hey, we don’t have any money to share”. That was a challenge. We had to pivot and think quickly. We had to furlough staff, which was terrible, and we just pulled back to what can make us money right now. We started doing live events on a pay-what-you-want basis. We took the paywall that was ready to go, switched it to a pay-what-you-want wall, and started addressing how the pandemic was affecting business travel. 

We would have 2 000 people sign up for a Zoom webinar, and around 10% of them would pay between $5 and $20. We did a different event every ten days for around three months. And we took from 10k to 30k per event – which really helped.

Then we started doing a pay-what-you-want model on the site, kind of like The Guardian. Do you want to give us some money? And did that until July 2020, when we introduced a metered paywall on Skift. 

Like other news sites at the time, we had fantastic traffic during that period. We don’t do CPMs, so advertising didn’t necessarily matter. But we had created a deeper relationship with readers who really needed us. The challenge for us, though, was at the time we put up the paywall, a lot of companies in the travel industry started their layoffs for real. 

We had to think about ways to re-engage the people that were still there. It was a challenging period, but we learned a great deal about being agile and flexible.

*The interview has been lightly edited for brevity and clarity.