Hey, I'm Alex Hilleary.

💡 I'm currently in ideation + building mode.

I grew up in North Carolina and now live in Brooklyn. I've also called DC, Cleveland, and The Bay Area home.

Outside of work I love running, skiing, basketball, and biking. I'm a geography / map nerd and love walking around cities. I listen to way too many history podcasts.

I've spent a decade working on the growth side of B2B early stage startups. While I've usually worn a marketer har, I've always lived at the intersection of everything GTM.
‍
Here's the brief arc of my career:

2016 - 2019

BoxCast (seed stage, live streaming platform) - New Market Verticals then Content Marketing

I joined BoxCast out of college as a Venture for America Fellow. At the time, BoxCast's main markets were churches and sports orgs. They wanted to get into local government. I acted as GM of that vertical and essentially took it from zero to one. I generated my own leads, created content marketing, built channel partnerships, and closed every customer along the way.

After that, I moved fully to marketing to lead our content marketing and marketing ops. In just over a year, I grew the blog from 10k to 72k monthly visitors to and helped us take the SEO channel to the next level.

2019 - 2022

Gather (inception to seed stage, hr tech) - Co-founder, COO + GTM

I left BoxCast to co-found Gather with with Brooks and John.

We had awesome three year ride, building a workflow software for people ops teams from the ground up. We joined Y Combinator in the S20 batch, raised some money, grew to a team of six, worked with 50+ companies. Just as we notched our top sales month and started to raise a new round of funding, we were opportunistically acquired by ChartHop.

At Gather, I ran our whole GTM function. What I'm most proud of is that almost everything we did was organic, through a community / thought leadership / SEO play. We spent less than $5K on ads / program spend in the course of our three years.

I also led our angel fundraising round.

2022 - 2025

ChartHop (series B to series C, hr tech) - Community then Growth Marketing+

While my co-founders and the rest of the Gather team went to build Gather into the ChartHop platform, I carved out a role for myself on the ChartHop marketing team leading community in an extension of that work from Gather.

I launched and ran a popular newsletter (13k+ subs), job board (1.2m+ views), and community (1k+ members). built a LinkedIn following of 33k. My favorite project was two live events I designed and ran called 2-Minute Talks (each had over 1k signups). Even as I moved on to a bigger role, community became one of our top five customer acquisition channels.

While it wasn't initially my intention, I took on broader marketing responsibilities across demand gen, brand, partnerships, content, and GTM ops.

Eventually, I lead a significant part of the marketing function through a period of transformation and renewed growth around more efficient channels. While my focus was growth marketing and demand gen, I had my hands in everything the marketing team did. I managed a few direct reports — an assortment of FT, PT, and agency folks.

In my last six months at ChartHop, I was a member of the nine-person extended leadership team.
‍
In June 2025, after establishing a leaner GTM engine and helping achieve our best two quarters in the last two years, I stepped away to go back into builder + ideation mode.

You can find me on LinkedIn.