In January of 2022, I skied a new hill for the first time in at least ten years. Our home mountain, Sugarloaf, is a crown jewel of east coast skiing. For the first years we skied there, I was living in DC, and just getting ski days in was a feat. Since moving back to Massachusetts, skiing has been primarily about getting my kids into the sport. Staying at our home mountain, especially a great one, made sense. But then, I finally took advantage of our access to Loon Mountain, in New Hampshire, and skied a few day trips with some friends.

After ten years on the same mountain, skiing somewhere new was like a revelation. Loon isn’t a giant and you probably wouldn’t ski there forever, but it is in a cool spot in the White Mountains and is really accessible to greater Boston. The revelation was less about being there and more about being in someplace new. For the first time in ten years, I picked up and used the trail map: I was forced to click into explore mode. After a decade of skiing at a place I know like the back of my hand, going into the unknown was a really cool feeling.

In March of 2022, I took a month-long sabbatical from my work at HubSpot. Instead of trying to write a book or renovate a room (some original aspirations), my sabbatical ambition was to get into explore mode.

Enter: the Indy Ski Pass. This pass gives the passholder two days of skiing at a bunch of independent (read, not corporately-owned) ski hills. While some of these places are quite large, in terms of skiable acres or vertical feet, most of them are on the smaller side. Sometimes they’re even in the same towns or ranges as the big, corporate resorts, but they tend to be a little less slick, have a little more duck tape, and Carhartt or Columbia instead of Helly Hanson. You may not spend a full week at one of these hills, but a day or two gives you a lot to explore.

So, for my sabbatical and for the 2022-2023 ski season, I bought an Indy Ski Pass.

It was a banner ski season, during which I managed 37 ski days and over 400k in vertical feet (top speed: 57.5 miles per hour). The exploration was really cool. I added six new hills to my lifetime list, all places I’d never skied before:

1. Waterville Valley
2. Jay Peak
3. Saddleback
4. Pat’s Peak
5. Bolton Valley
6. Black Mountain, NH

There’s nothing like driving up, finding a parking spot, and getting to a chairlift at a brand-new place. Even if it’s a 60 year-old creaking double, it’s new to you. The indy hills had some of the cheapest food in their cafeterias, friendliest staff around the base area, and funkiest setups you could imagine. Riding the chairlift during the midweek brings you all kinds of characters, from the 10 runs by 10am retirees to the 1-day a year locals, and talking to them makes skiing a community.

I got to thinking about what makes smaller companies worth competitors to bigger ones. No one is going to outmatch Sugarloaf’s alpine areas nor can a small hill compete with the slickness of Vail’s billions in ski lifts. Those could be negative, but for good operators (and marketers!) constraints breed a cool kind of creativity. You don’t need the biggest, best, or fastest to have a great ski experience.

Not all of the corporate ski mountain stuff is required–you don’t need umpteen signs to be safe or to get where you’re going. A bunch of niftily uniformed “ambassadors” probably offer less than one competent and friendly cashier. It’s cool that the guy loading the chairlift is also the guy who took my money and the guy grooming the place back into shape that night. He’s definitely the kind of guy you’d want to hand a beer to at the end of the ski day.

A little focus on the customer experience can go a very long way–Bolton Valley’s U-shaped hotel/restaurant/baselodge was impossible to figure out, but the ticket booth guy in the friendliest way let me, an obvious first-timer, know what to do and where to go. They could probably use an architect and some signage, but a person who cares about their job more than made up for it. Riding the lift with a 50-year skier at Waterville Valley made me a lot more stoked to get out there than any amount of ski-bro marketing copy.

In terms of widely-applicable digital strategy, I think they’re onto something in a few ways: marketing content, experience-driven communications, and the opportunity to make the skiing experience even better.

The Indy pass used a lightweight model and some cool digital marketing tactics to make the overall experience really good. Their website assumes that you want to go skiing at their partner resorts, and they show maps, link to details, and give you trip planning details. None of that necessarily benefits Indy Pass, but it benefits you, the visitor. Imagine linking to a service just because it’ll help your customers without getting anything in return; even if the places gave some referral cash to the Indy Pass folks, it was clear to me that serving the skiing passholder is their primary goal.

In the customer experience, good digital communications are vital: I really liked getting an email that said where I was, where I redeemed the pass, and how many days at the resort I had left. The separate text message wasn’t too much. I liked getting event triggered, detailed messages because they made me feel connected to the service.

There’s probably some opportunities for the Indy Ski Pass folks to help make skiing trackers like me happier. They could communicate more about the overall season: you've been to X places, skied Y days, or just went to your nth state. Customer experience isn’t just digital: I now have at least 5 plastic cards containing RFID chips that unlock only one ski area’s gates. Why couldn’t the chips be made to unlock more lift gates? Why couldn’t Indy Pass send me a card that works all over? (Do I even need a card when I carry a phone?) The online world has conditioned us to expect more from our vendors. It’s hard to make a truly extraordinary customer experience, but that’s where the real juice is.