The Startup Journey

It's Great to Meet You: A Note from Superpath's New CEO

Alex Hilleary
November 21, 2025

This post had been edited from it's original version shared 11/19 in the Superpath Pro community for a broader audience on the blog.

Hey Superpath! It’s great to meet you (if I haven’t already).

I’m honored to have Jimmy’s trust in leading Superpath into this next chapter as the new majority owner and CEO.

I hope to meet everyone in the coming months. Until then, I want to share more about my background, my thoughts on community, and my goals here. At the end, I also answer a few questions you might have about the transition.

Who am I?

I’m Alex. I’m a startup marketer and founder who began in content and developed an obsession for professional community design.

For the first few years of my career, I was primarily a content marketer at early-stage startups.

My first gig in the early 2010s introduced me to inbound marketing and I immediately latched on. Several years later, I was running a company blog as a one-person content team, obsessing over traffic, and reading every post from this guy named Jimmy Daly.

In early 2019, I became the go-to-market co-founder of an HR tech startup called Gather. It was a scrappy operation (it’s a point of pride for me that we didn’t spend a dollar on advertising beyond the Google Ad credits they give you). So content was the foundation of our marketing.

Somewhere along the way, content became community. I was talking to dozens of solo Heads of People at startups and I kept saying, “Oh you should really talk to so-and-so.” Next thing I knew, I built out a 1:1 program so these prospects could meet each other and started writing a weekly newsletter synthesizing thoughts from the conversations I was having.

Building community at Gather ended up helping to establish trust with prospects and served as an effective marketing strategy. It also set up my passion for designing peer-to-peer connections.

When ChartHop acquired Gather in 2022, I created a marketing role for myself focused on continuing to build community in the People Ops (HR) space. I grew the newsletter to 15k+ subscribers, launched a channel-based forum (similar to Superpath) with over a thousand members, crafted virtual and in-person events, and operated an industry job board that surpasses a million visits. It was very fulfilling work.

But as it often goes, over time, I was needed for other things. As I took over other facets of the ChartHop marketing operation, I handed off most of the community work to others on the team.

This year, I decided I wanted to go back to building community. I left my full-time job at ChartHop this summer with the intention of starting a community business from scratch, but this time working with marketers.

From my experience and from conversations with other community designers (like Jimmy!), I’d established a set of design principles for community success.

While I wasn’t actively looking to buy, I was open to acquisition for the right opportunity. Superpath was the perfect fit. It was my chance to return to the content marketing world and work with Jimmy.

On Communities

Content marketing is evolving rapidly. AI is changing everything for a function with a well-established template. It’s easy to fall behind, but there are huge opportunities for those who keep up.

In a moment like this, professional peer communities can serve a very important role because:

  • Posts in public spaces (read: LinkedIn) have an agenda, are filled with AI slop, and aren’t optimized for the right, nuanced answer.
  • ChatGPT isn’t effective for solving problems that are niche and require judgment (i.e. “Is this industry conference actually worth going to?”).

I believe the best answers come from peer operators who are working on the same problems that you are and are open to sharing truthful learnings.

My goal is to create spaces that use your time well, help you make relevant connections, and get your questions answered thoroughly and with nuance.

A successful professional community isn’t about how much time you spend engaging with it. The best communities provide maximum value for your time.

On Superpath

This corner of the internet is special. Jimmy created something amazing here and you all brought it to life. As I fill some big shoes, I hope to earn your trust.

I’ll experiment and rely on your feedback for what works and what doesn’t.

I’m excited to continue working with Jimmy, Eric, Kisha, and Chloe to build the best content marketing community online and offline.

Cheers,

Alex

Answering your questions

What’s changing about Superpath day-to-day?

Your day-to-day Superpath experience will stay the same, but expect new programs for pro members and design tweaks to existing ones.

Are there any changes to membership, access, or events?

No.

Is Jimmy gone?

No. Jimmy remains a minority owner and part-time employee contributing to Slack, the podcast, the blog, and more.

What about Eric, Kisha, and Chloe?

They’re still here! I’ve enjoyed working with them over the past few months and look forward to relying on their deep knowledge of this space.

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