Building Culture at Workbrew: Hackathons in a Remote-First Company
As anyone who has worked remotely before knows, it’s tough to build a shared sense of culture across 10 time zones.
Operationally, our product engineering team uses the Shape Up methodology, which means that product work is focused into 6-week “cycles” with 2 week “cool-downs.”
So during our last cooldown period, after shipping Workbrew 1.2, we tried an experimental “Hack Day.” Our goals were to prompt cross-team collaboration and produce artifacts from the Workbrew API that our customers could potentially use. But at Workbrew, these events are about more than what we build — they’re about how we build it together.
Remote work takes work
As a remote-first, globally distributed company, collaboration isn’t left to chance — it's something we actively design and invest in.
Our team brings deep experience from companies like GitHub, 37signals, and Cloudflare, where remote work isn't just an adjustment — it's a craft. That shared experience set the foundation — but it was the hackathon that sparked something even deeper.
"The hackathon gave us something rare — a little more camaraderie, and a little more room for ideas to grow without the pressure to be perfect," one engineer shared.
During the hackathon, that mindset meant deeper focus, stronger collaboration, and the freedom for ideas to emerge naturally. Trust and autonomy weren’t obstacles — they were accelerators.
While our Shape-Up cycles drive focused product development every eight weeks, we saw the cooldown period as an opportunity to do something different:
- Cross-team collaboration beyond daily roles
- Customer-first exploration based on direct feedback
- Creative freedom without the pressure of long-term maintenance
By intentionally creating space to work differently, we unlocked fresh thinking — and strengthened the connections that make remote collaboration thrive.
The results stretched far beyond the projects delivered:
- Camaraderie: Celebrating unfinished experiments and small creative wins.
- Creative risk-taking: Turning small sparks into ideas with real customer potential.
- Role-stretching: Engineers stepping into product, design, and customer advocacy roles.
- User empathy: Experiencing the API firsthand revealed actionable ways to reduce friction and drive value for customers.
As one participant put it:
"Seeing small ideas come to life, and realizing how quickly we could help customers in meaningful ways, was inspiring."
Iterating to Improve
Our first hackathon in this format exceeded expectations. Moving forward, we’ll be integrating hack days into our Shape Up cycle to build a stronger, more creative, and more connected company.
By making space to experiment together — across oceans and time zones — we’re not just extending what Workbrew can do.
We’re extending what Workbrew can be.
Code Block
#!/bin/bash
# Check for Homebrew in supported installation paths.
if [[ -x "/opt/homebrew/bin/brew" ]] ||
[[ -x "/usr/local/bin/brew" ]] ||
[[ -x "/home/linuxbrew/.linuxbrew/bin/brew" ]]
then
echo "Homebrew is installed."
exit 0
else
echo "Homebrew is not installed."
exit 1
fiAs anyone who has worked remotely before knows, it’s tough to build a shared sense of culture across 10 time zones.
Operationally, our product engineering team uses the Shape Up methodology, which means that product work is focused into 6-week “cycles” with 2 week “cool-downs.”
So during our last cooldown period, after shipping Workbrew 1.2, we tried an experimental “Hack Day.” Our goals were to prompt cross-team collaboration and produce artifacts from the Workbrew API that our customers could potentially use. But at Workbrew, these events are about more than what we build — they’re about how we build it together.
Remote work takes work
As a remote-first, globally distributed company, collaboration isn’t left to chance — it's something we actively design and invest in.
Our team brings deep experience from companies like GitHub, 37signals, and Cloudflare, where remote work isn't just an adjustment — it's a craft. That shared experience set the foundation — but it was the hackathon that sparked something even deeper.
"The hackathon gave us something rare — a little more camaraderie, and a little more room for ideas to grow without the pressure to be perfect," one engineer shared.
During the hackathon, that mindset meant deeper focus, stronger collaboration, and the freedom for ideas to emerge naturally. Trust and autonomy weren’t obstacles — they were accelerators.
While our Shape-Up cycles drive focused product development every eight weeks, we saw the cooldown period as an opportunity to do something different:
- Cross-team collaboration beyond daily roles
- Customer-first exploration based on direct feedback
- Creative freedom without the pressure of long-term maintenance
By intentionally creating space to work differently, we unlocked fresh thinking — and strengthened the connections that make remote collaboration thrive.
The results stretched far beyond the projects delivered:
- Camaraderie: Celebrating unfinished experiments and small creative wins.
- Creative risk-taking: Turning small sparks into ideas with real customer potential.
- Role-stretching: Engineers stepping into product, design, and customer advocacy roles.
- User empathy: Experiencing the API firsthand revealed actionable ways to reduce friction and drive value for customers.
As one participant put it:
"Seeing small ideas come to life, and realizing how quickly we could help customers in meaningful ways, was inspiring."
Iterating to Improve
Our first hackathon in this format exceeded expectations. Moving forward, we’ll be integrating hack days into our Shape Up cycle to build a stronger, more creative, and more connected company.
By making space to experiment together — across oceans and time zones — we’re not just extending what Workbrew can do.
We’re extending what Workbrew can be.
3. IT Admins have questions. We weren’t sure what to expect, but so many folks had specific implementation queries. Others were curious about what Workbrew is up to. It was a non-stop flow of awesome conversations, and we ran out of Homebrew Cheat Sheets and Implementation Guides.
4. MacAd.UK has great bean bag chairs – the Chill-Out Zone was a super comfortable place to talk about CVEs.
5. The wonderful MacAdmins Foundation offers grants for folks who want to attend but aren’t in a position to fund the trip. For those looking to attend MacAdmins PSU, their applications are open.
A big thank you to the MacAD.UK team and we’re excited to be back next year.
If you missed it, check out Brandon’s talk on Balancing the Needs of IT, Security, & Engineering Teams at Scale
3. IT Admins have questions. We weren’t sure what to expect, but so many folks had specific implementation queries. Others were curious about what Workbrew is up to. It was a non-stop flow of awesome conversations, and we ran out of Homebrew Cheat Sheets and Implementation Guides.
4. MacAD.UK has great bean bag chairs – the Chill-Out Zone was a super comfortable place to talk about CVEs.
5. The wonderful MacAdmins Foundation offers grants for folks who want to attend but aren’t in a position to fund the trip. For those looking to attend MacAdmins PSU, their applications are open.
A big thank you to the MacAD.UK team and we’re excited to be back next year.
If you missed it, check out my talk on Balancing the Needs of IT, Security, & Engineering Teams at Scale
Code Block
#!/bin/bash
# Check for Homebrew in supported installation paths.
if [[ -x "/opt/homebrew/bin/brew" ]] ||
[[ -x "/usr/local/bin/brew" ]] ||
[[ -x "/home/linuxbrew/.linuxbrew/bin/brew" ]]
then
echo "Homebrew is installed."
exit 0
else
echo "Homebrew is not installed."
exit 1
fi