What I learned watching a company grow from 15 to 1,300 people

Or, 12 things I wish I knew 5 years ago

Billy Roh
Opendoor Design
3 min readSep 12, 2019

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Illustration by Nicolas Solerieu

I’ve been at Opendoor for 5 years and have watched it grow from from 15 to 1,300 people. I’ve learned a lot by making a lot of mistakes along the way. Here are 12 things I wish I knew 5 years ago, when I first started at the company.

Product development

Be resilient when pursuing big ideas.

They often don’t work the first, second, or even the third time, but each time you try, you’ll learn something and get closer to succeeding.

Draw a clear line between your team’s output and the company’s bottom line.

The clearer the line is, the easier it will be to ask for more resources for your team. The less clear it is, the harder it will be to fight for your team’s continued existence.

The secret to not shipping your org chart? Customer research.

Your customers will give you a holistic perspective of your product. They won’t be concerned with orgs, seams, and individual incentives.

Metrics and incentives

Avoid playing metrics theatre.

Make sure each metric ties back to an action item. Otherwise, you’re just looking at numbers to make yourself feel more informed.

Metrics exist to incentivize behaviour.

If you have too many metrics or if they’re too complicated to understand, they will fail to do their job.

Use simple metrics to avoid thrash.

Complicated metrics tend to be brittle and get quickly thrown away as company priorities change. Simple metrics (e.g. DAU and CSAT) tend to be more robust.

Being an effective IC

Clear, concise communication skills are a powerful way to multiply your output.

This is especially true for written communication as clear writing is easy to read and easy to share.

Being kind and easy to work with is hugely underrated.

You can only do so much by yourself. To achieve great things, you have to convince others to work with you.

Give your manager a clear proposal on how to help you.

They want to help, but their time is very limited. Don’t make them think too hard.

Miscellaneous

Don’t deify founders and early employees.

The reality is that they’re just figuring things out as they go along just like you. Don’t be afraid to question their thinking and decisions.

Give yourself 48 hours to celebrate or vent.

Decisions and events that give you grief or joy will change in a few days. Most startups are short-lived and their goings-on even more so.

Change is hard, but change management is harder.

Make sure people understand not just what is changing, but why it’s changing, when it will happen, and how it will affect them.

The pace of a startup can be unrelenting. I was only able to realize these lessons for myself by setting aside time for self-reflection. For me, this has meant writing, meditation, and therapy to better understand the path that I’ve taken and the path I want to continue on.

If you’d like to work with an amazing team like I have, check out our jobs page! I can honestly say my growth wouldn’t have been possible without the help and support of such a talented group of people.

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