🐶 Hailey is coming to life!

Coming up for air after two weeks of code

I’m building HelloHailey in public.

I share my metrics, successes, failures, and all the ups and downs of being a bootstrapped solopreneur.

Want to follow along?

Get my backstage pass


Hailey is coming to life!

After six weeks of researching, interviewing, and writing, I finally got to start coding 🤓

Two weeks later, Hailey is a living, breathing (not really…) office puppy.

As a personified, (remote) office dog, she kickstarts conversations and makes people laugh. But she’s not ready for the big leagues yet…

In this update, I’ll share what she’s learned so far and how she’ll be introduced to the world in a four-stage rollout plan.

Hailey is the perfect (Slack) party host

In my last update, I set my vision - to create fun and fulfilling remote workplaces.

I believe the “Slack Party” concept will do just that for remote teams.

Two weeks of progress

Hailey’s already learned a few tricks 🐶 (after lots of patience and treats):

  1. 💻 She can be installed via a custom dashboard.

  2. ☁️ She lives in the cloud (on Heroku).

  3. 💬 She engages directly with new team members when they join her Slack channel.

  4. 🧠 She learned twenty conversation prompts - with gifs and her own responses - and sends them on a schedule.

But progress wasn’t made without a few unplanned surprises:

  1. I need a custom dashboard - I initially planned on having users download the app from the Slack App Directory rather than building out a custom flow. But I decided to build one to avoid delays related to their submission and review process and, eventually, more flexibility in customizing my onboarding flow.

  2. Scheduling is hard - I wanted to support custom time zones and working hours on a team-by-team basis. For now, Hailey will only send messages at fixed times that make sense for US time zones.

Hailey is nearly ready to be released to the world. But she’ll start with baby (puppy?) steps.

Releasing in stages

Reid Hoffman, founder of LinkedIn, once said:

If you aren’t embarrassed by the first version of your product, you've launched too late.

I agree with this sentiment, but that doesn’t mean I’ll be opening up to everyone on day one. I’ll release to just enough users to learn. Then I’ll go through cycles of iterating and releasing to more.

Eventually, I’ll run out of early users and launch to the world.

Stage 1️⃣ - Friends

No, I’m not talking about Ross, Joey, and Rachel 🙄

I’ll start by using the product myself in Slack workspaces full of personal friends. It’s a different dynamic than the professional teams I’m building for, but I’ll still learn a few things (and fix some bugs).

Goal - launch before Christmas 🎄 (December 25).

Stage 2️⃣ - Friends’ Teams

A handful of close engineering/product manager friends will try out HelloHailey with their teams.

This will be my first opportunity to learn from a real team of unbiased users that don’t know me.

Goal - launch by January 15.

Stage 3️⃣ - Waitlist Users

Sixty people have filled out the waitlist survey. I’ll gradually release to my waitlist users over 2-4 weeks.

Want to be one of the first users to try out HelloHailey with your team?

Grab an invite

Stage 4️⃣ - Open the Floodgates

After exhausting my waitlist, I’ll open up HelloHailey to anybody on the internet!


New Year, New Users

I’ve switched to bi-weekly updates on two-week sprint cycles. I prefer higher quality (but less frequent) updates.

My next update will be in 2021. I hope to have some valuable product learnings to share with you by then.

More importantly, we’ll all be able to put 2020 behind us…hindsight is 2020, right?

Want to find out what I learn from my Stage 1 launch?

Get next sprint's update