John August

One year ago, we launched Highland Pro. I was confident in the app itself, having put it through its paces over its multi-year development journey. I’d written dozens of scripts and novels in Highland over the years, and knew that Highland Pro was the best version we’d ever made. Our beta testers loved it, too.

Still, I was nervous about the launch itself.

We were switching from a paid upfront model to subscription. The 30-day trial period made it easy for users to get started in the app — but would they stick around?

It turns out, they did!

Roughly 60% of our trial users converted to paying customers. Monthly recurring revenue continues to grow each month at a steady, sustainable level. It’s not a hockey stick, but rather a reassuring climb.

Our first year of Highland Pro brought in more money than the last four years of Highland 2 combined. Most of our annual subscriptions have renewed. We can approach the next twelve months knowing we’re on a solid foundation.

Money is great, but honestly the biggest advantage to a subscription model is that it properly aligns the interests of an app and its users. Rather than chase new customers, we can make the app better and more delightful for existing subscribers. We’re grateful to the thousands of writers who rely on Highland Pro.

On our official blog, Daniel wrote about what we accomplished in this first year, including stats and details on our many new features.

Here I wanted to share some of personal observations as Highland Pro’s part-time CEO and biggest fan.

Twelve lessons we learned

Highland Pro’s first year was successful, but certainly not flawless. Some choices paid off. Others didn’t.

1) We worried that Highland 2 users wouldn’t make the leap to Highland Pro. They did. Three quarters of Highland 2’s weekly active users made the switch in the first two months. Our core users embraced the change and saw the advantages to Highland Pro.

2) Likewise, we worried too much about complaints from people who “don’t like subscription software.” These people were not going to be happy no matter what we did. That’s okay! Let people have their opinions.

3) We moved our #TeamHighland community from Slack to Discord. They’ve been instrumental in helping us quash bugs and develop new features. Discord can feel messy and chaotic, but it’s easy to see the activity. Traditional forum software ends up becoming a ghost town.

4) As a company, we all needed to take a more active role in the support queue and #TeamHighland Discord. Customer service is not a separate department, especially with a subscription app. It’s much easier to fix bugs when you directly engage with the people encountering them. Often, they’re using the app in unexpected ways.

5) Onboarding and paywalls matter — but what’s going to work is not at all intuitive. We A/B tested multiple versions of the paywall and always guessed wrong. For now, a hard paywall when you first launch the app appears to be the most successful.

6) iOS and iPadOS are uniquely frustrating. For years, Highland users have clamored for a version they could use on their iPads and iPhones — but when you give it to them, they’re understandably frustrated by the limitations and compromises. Our reviews for the iOS version are considerably lower than macOS version, and I get it. If your only experience with Highland Pro is on the iPhone, you’ll be disappointed. Whereas if you see the iPhone app as a companion to the “real” version on the Mac, your expectations are appropriately modest.

7) One of the biggest issues for iOS/iPadOS is iCloud syncing. It’s a black box that should “just work,” but often doesn’t, leaving users frustrated and developers at a loss to explain exactly what’s happening. We did a lot of work to improve syncing, including robust new backup features to protect users against data loss in case something goes wrong. But it’s not as seamless as anyone would hope.

8) We expanded the team. This year was our first with a dedicated, full-time marketing director. Daniel tackled all the projects we never fully understood, including revamping our SEO. We also brought in our first outside coder on contract. We learned how to set milestones and appropriately scope new features. It was good practice.

9) We used the latest Apple frameworks as much as possible, but held off on implementing Liquid Glass for the UI. This was the right choice. On iOS, Liquid Glass is sometimes delightful. On macOS, it’s generally a distracting mess.

10) We sponsored the Austin Film Festival this year, including hosting the opening night party. We went all out: printed materials in every conference bag, hundreds of Team Highland t-shirts, and a special conference session about Highland Pro. The four of us who attended had a great time and met interesting writers. We pre-sold a lot of Scriptnotes books. It had limited measurable impact on Highland Pro sales, however. Our promo codes got redeemed at a surprisingly low rate.

11) We experimented with sponsoring smaller film festivals and conferences, focusing on university-affiliated programs. (Highland Pro is free for college students.) These ended up being pretty cost-effective, particularly when you’re giving away subscriptions and t-shirts.

12) For accounting reasons, we moved all our apps to a new App Store account tied to our LLC. It was only after the first two months that we realized our Small Business Program certification hadn’t transferred. We were paying Apple 30% rather than 15%. We got it fixed quickly, but oof. It’s the things you don’t even consider that can cost you the most.

Looking back at a year of Highland Pro, my biggest takeaway is gratitude. I’m endlessly thankful to the team who built it, tested it, and put it out there in the world. I’m grateful to everyone who tried it, whether they ended up subscribing or not. One of the biggest obstacles for a new app is inertia. Writers are used to Microsoft Word or Final Draft, even if they complain about them. I’m thankful to every writer who allowed themselves to be uncomfortable for a few minutes and try something new. (And better!)

I have the unique pleasure of being Highland Pro’s co-creator and most active user. It’s where all my words go. I’m writing inside it for hours each day — including this blog post, which I will fling to the team for comments. (And in the process, catch weird Fling bugs which Nima will quash.)

To me, Highland Pro feels indispensable and almost inevitable, so it’s wild to reflect on just how much has happened over the past 12 months. For the next few months, we’re focused on stability and accessibility improvements in the app itself, and better community engagement. But as always, we have ambitious plans for Highland and beyond. I’m already looking forward to next year’s blog post.