Growth Experiments: Wins, Losses and Lessons Learned

I’ve spent an enormous amount of time thinking about how to grow Superpath. I’ve tried dozens of things and have narrowed in on a handful that work well. While these experiments aren’t the highly scientific kind that a proper growth marketer might run, I have a good sense about what’s worked and not worked with Superpath. And because I’m the only employee, I have the benefit of a very tight feedback loop.

The first thing I want to emphasize is that macroeconomic conditions influence demand, and that is really, really important. I call this “macro demand” and it’s an important gut check before you dive into specific growth tactics.

You cannot achieve growth without demand, so I think about growth as a downstream effect of demand. A funnel is the simplest way to visualize this:

• “Macro demand” - Do economic conditions that make my product/service useful?
• “Micro demand” - Is this specific version of this product or service aligned with the macro demand? This is a fancy way of saying “product/market fit.”
• Accessibility - Is our product/service easy to understand? Is it obvious how signing up will help the customer?
• CRO - Is it easy to buy?

I constantly assess how we are selling and what we are selling. Superpath has a flexibility that larger companies don’t who can improve their messaging and CRO, but can’t easily change what it is they sell. If our offerings don’t sell, we just change them. I think some of these lessons here can help marketers support their companies’ growth goals, with or without that benefit.

Lesson #1: Sell the right thing

The Superpath job board used to get 15 to 20 new jobs per month. It was a very reliable revenue stream. That fell off massively in 2023. At first, I thought it was a conversion rate optimization (CRO) problem. I tweaked copy and buttons, but nothing happened. The macro demand was way down and there wasn’t anything I could really do to boost job board revenue. Perhaps I also had trouble accepting that content hiring was way down! 😭I now try to look at each of our lines of business with the same discerning eye. Should I make the landing page better and clean up the messaging? Or are we selling something that people don’t need right now?

You can optimize a landing page until your eyes bleed, but it won’t help it sell if people don’t need it to begin with. Over the years, we’ve launched and retired a few services. Our current slate reflects what I believe to be most closely aligned with what our target audience needs and can get value from.

Most marketers can’t easily change what they sell, but they can influence positioning. Using the job board example again, I could have shifted the messaging to tap into the increased need for freelancers. As hiring slowed, more companies relied on freelancers. The job board infrastructure was perfect for finding great freelancers, but I didn’t move on that idea fast enough. That was a missed opportunity in retrospect.

Understanding the macro forces that create headwinds or tailwinds for your business is really important. It is among the handful of most valuable skills a marketer can hone.

Lesson #2: Launch and relaunch regularly

Launching sells. Every spike in sales on our Stripe dashboard over the last five years directly correlates with a launch or relaunch. Here are a few examples:

• In 2020, when we first launched Superpath Pro, 25 people signed up in just a few days. In October 2024, when Eric and I relaunched it, we drove 30 new signups in a few weeks.
• When our partner program turned stale, I leaned on this same strategy. I cleaned up the offering, created a landing page to showcase examples, and relaunched it. I filled up three months of ad inventory in a few days.

Launching is a big deal. (You obviously need something to launch!) Relaunching is easier, and in addition to the potential sales boost, it’s also a chance to refresh your offering. To do it well:

• Step back and try to honestly assess your product or service. Is it delivering on the promise you initially set out on?
• Ask your customers what they think could be improved. Adding value and improving the customer experience are great talking points in a relaunch.
• Try to balance infrastructure improvements (mostly valuable to you) and feature/experience improvement (mostly valuable to your customers).

You can’t do this too often, lest you become the company that cried wolf. But I think you can relaunch at least two times per year with more product updates in between. Lesson #3: Free-to-paid is harder than it soundsSuperpath has been adding about 500 new free members every month for several years. But our paid membership, Superpath Pro, has grown in fits and starts. There are a few reasons for this:

• Free members often want the free version. They aren’t necessarily trialing Superpath to see if the paid offering is for them.
• Free members are a slightly different persona. Many of our free members are freelancers, and most of our paid members are in-house.
• The free version of Superpath isn’t a very good teaser for what’s included. It mostly focuses on conversation in Slack, which is only one small part of the Pro offering.

We’ve taken a bunch of steps to improve our free-to-paid conversion, including:

• Adding upsells to the onboarding for free members
• Sending monthly promo emails to our free members
• Teasing the best Pro threads each week in #announcements.

But it’s not enough, and we need to do more. We’ve just launched a 30-day free trial of Superpath Pro so people can experience all of it for a month before deciding. I think this is exactly what a lot of folks need to really assess the paid membership.

The next thing I’m thinking about is monthly workshops that are free for Superpath Pro members and cost $50 to $100 for everyone else. I am also considering a virtual event with a similar cost structure. Content will be available to Pro members later in our app.

There’s so much great stuff happening in Superpath Pro, and for the most part, Pro members are the only ones that know about it.

Lessons #4: Beat the drum

This brings me to the next lesson: we can never stop talking about Superpath Pro (and our other offerings).

This isn’t so different than content marketing. You have to keep publishing and distributing so that you’re top-of-mind when the time comes.

We don’t publish a ton of top-of-funnel content because we already get more than enough site traffic and free signups. Instead, I try to focus my content creation energy on the offerings: new things we’re doing in the community, upcoming events, takeaways from the most interesting threads, and so on.

I find this hard to do. It’s not my instinct to take to LinkedIn and talk about myself or the business. I’ve had to make a deliberate effort to do it, which means writing down ideas as I have them, scheduling stuff out for the week, and making sure to follow up on comments.

When you’re actively doing it, this is hard to measure. When you aren’t, it’s actually much easier to measure. We see fewer sales when I post less on LinkedIn. I don’t feel the need to try to attribute “beating the drum” to sales because it’s so obvious to me.

Lesson #5: Make it easy to say “yes”

I’ve dreamed up products and services that make perfect sense in my head. Then, I launched them to crickets. The biggest reason for this is that I didn’t make it easy for potential customers to see it, like it, and buy it. Everything you sell has to be very easy to say “yes” to.

Here are two examples. One I think I’ve solved and the other is still in the works.

In the summer of 2023, we paywalled a portion of the Slack community for the first time. This meant that Superpath had three tiers: free, the paid Slack community, and Superpath Pro, which included the paid Slack channels as well as other stuff. This all made sense to me, but it created a ton of confusion for potential members. I got several emails each week from interested folks who weren’t sure which plan was right for them. Worse, the middle tier didn’t have a name, so we just called it “the paid Slack plan.”

I can’t quantify how many sales we lost because a prospective member hit the landing page, got confused, and lost interest, but I’m sure there were plenty. As part of the fall 2024 relaunch, we consolidated the two paid tiers into one: Superpath Pro. That, plus the relaunch, has boosted sales at least partially because it’s very clear.

The other example, which is still very much in progress, is our marketplace. The offering is solid and our customers are happy, but it’s too hard to sell. We vet and source freelancers, then handle all the back office work like payroll and 1099s. In this case, the pricing is the problem. We charge a platform fee, then bill the cost of the content plus a small markup. Most customers pay $500/month for up to $5,000 in content spend, plus a 5% fee. The platform fee is billed automatically and the rest is invoiced. If a customer spends more than $5,000 on content, the platform fee increases. If they pay via ACH, the 5% fee is waived.

You can see the problem here. It’s way too confusing. It starts with “We make it easy to work with freelancers” and quickly devolves into a complex pricing scheme. It also means I have to expend a lot of effort on sales for a relatively low-priced service that most prospects say “no” to anyway.

I don’t have the solution yet, but the problem is very clear. Prospective customers can’t easily say “yes,” so most don’t.

Back to Basics

A few weeks ago, I wrote in The only 2025 marketing plan that’s guaranteed to work that getting back to basics is THE marketing plan for 2025. To really drive home this point, I think that many marketers had gone deep into the advanced and nuanced parts of marketing. The current environment is forcing us to rethink that, making the “basics” more important for us (because we don’t know the advanced version yet) and for prospective customers (because they never cared about the fancy stuff anyway).

The macro environment is changing a lot right now. I’m still sorting out exactly what that means for Superpath since it’s not entirely clear what it means for content marketers.

I expect that our growth opportunities and challenges will fluctuate over the next few years, much as they have in the last few. I’m committed to letting the macro demand guide what comes next, all while trying to improve and simplify today’s business.