Caveday
Business Case Study
THE PROBLEM
So many people in NYC are doing amazing work ineffiently.
They’re working alone.
They procrastinate.
They’re distracted.
THE BRIEF
How can we build a community around deep work
and make it a transformative, energizing, experience?
MY ROLE
Co-Founder, Head of Brand Experience
My cofounders, Jeremy Redleaf and Molly Sonsteng, and I wanted to build community around deep work.
We researched the science of productivity and IRL experience design to build the first ever Cave Day– a full day of deep work where we commit to our most challenging tasks, take breaks together, and celebrate our progress at the end of the day. Our first event on January 15, 2017 sold out.
I designed the first round of our brand with a very simple style.
Two months later, we were featured in FastCo as the future of work.
I went “into the Cave” to develop an ownable brand as we were developing an event into a full-on business.
About 9 months in, we were starting to realize that this business had potential to be bigger than just a monthly 50 person events. We started documenting our process and soon after, trained other facilitators and launched Caveday chapters in Los Angeles and DC.
We started asking our customers about their needs and pain points.
Event tickets turned into monthly membership.
Full day events evolved into half day Caves.
We updated our format to include novelty in its structure.
And added in some workshops to help people manage their time and workload.
It became a tool that I used to build out our corporate training program.
We heard people across the world were interested in joining.
So we started experimenting with Remote Caves in 2018.
I also developed Caveday’s first workshop to teach people about the benefits of deep work and flow.
Over the years, we’ve worked with some amazing partners.
In January 2020, we were aligned on raising money to open up the first ever work studio. Think: Soul Cycle, but for Work.
Ahead of our fundraising, I led a brand redesign.
We hired our first photographer and designer and created a more sophisticated and dark look and feel for Caveday.
Then the pandemic hit.
We found ourselves running an IRL events business.
We pivoted the business to a virtual coworking community.
The category didn’t really exist before, so we started making up the rules.
We began with generosity: offering free workshops on how to WFH.
It certainly was a weird time.
These workshops became a perfect marketing tool for new members.
I led over 75 workshops in 2020.
Our mailing list started to grow quickly.
By the end of 2020, we had 10x’d our membership.
This little side hustle was actually becoming a full-on business serving a global audience. And yet, our back end felt like it was kept together with duct tape and staples.
Q4 2020 was spent updating, integrating, and migrating our systems.
We began getting really good with list segmentation and email marketing.
I started writing biweekly newsletters offering productivity tips and insights.
Our new systems for booking and membership management unlocked a new tool:
DATA
This, combined with segmenting, allowed us to amplify our marketing, tailor our messaging, and continue to grow our membership at a healthy rate.
We began expanding our schedule of Caves to offer more start time for people working with us from around the world.
This forced us to get really good at delegating. Including our training process.
Which was helpful as we hired 30+ facilitators in 2020-2023.
A few of our facilitators we call “Cave Guides”
We wanted to increase word of mouth marketing.
Our strategy was to launch an affiliate program and create buzz-worthy merch.
500x
our customer base
We started Caveday because we know the power of
community + deep work.
We wanted to serve people. Not spend our time writing emails.
So we’ve spent a lot of time creating
workflows and automations.
It’s not a very visual thing to show in a case study, but worth mentioning that learning to create email drips for new members, marketing automations, and cancellation winback flows has saved the company tens of thousands of dollars and weeks worth of time.
Creating automations also gave us the bandwidth to focus on creating our first in-person retreat, and first in-person event in 4 yeras.
RESULTS
In 8 years, we’ve had some impressive success.
It became a bootstrapped, full-time job for my cofounders and I.
Plus, we hit some huge milestones
$80K
monthly recurring revenue
56
staff members hired and trained
75+
corporate clients
20k
newsletter subscribers
475
avg bookings per day
and got tons of press
Sunday NYT Business section feature in July 2021