This was 2019. The company was probably 1,500 people. Opendoor is heavily operational, so call it a 1,000 people on the ground in various locations helping us buy and sell homes in those markets. Then 300 to 500 corporate employees; about 40 people in Product and Design and 150 in Engineering. Somewhere in that ballpark.

I opened this doc prior to joining Opendoor, but after accepting the offer. And that was intentional. I actually asked for that. I said "send me as much stuff that I can consume asynchronously before joining the company" and I think that was really helpful. So even before I had Opendoor email address they started just adding my personal email address to check out some of the docs that are in here.

There was a suggested structure of people to meet. This was helpful because what this allowed to happen was the executive assistant I ended up working with just went ahead and set these meetings. Before I joined but once my account was made, she went in and pre-populated a whole bunch of meetings. So day one I walked in and I already had a calendar of people to go meet, things to go do. I wasn't starting at square one. This differs depending on the level you're coming in.

If I were coming into an IC role meeting so many people probably wouldn't be the first goal. The first goal would be meeting my team, going deep with them, understanding the roadmap, and maybe going and doing a lot of customer development work, which was a part of what I had here.

For me, it was start with internal meetings, getting demos of the product, meeting the team, meeting the rest of the executive staff. And then by weeks four and five, go visit some markets. And while visiting those markets, not only meet the teams there, but also go and understand the consumer experience and the product. How an actual customer experience it.

Opendoor's not a purely technology business. It wasn't even available in San Francisco, so I couldn't try it in the market that I'm in. So it was, okay, go to Phoenix and actually go tour some homes, go see how this is done in the market. Same with Atlanta.

There were certain things I asked for which are all the links. Send me any roadmap documents, send me any vision documents, send me previous board decks, send me company financials. If you can get me into looking at the dashboards that you've already created, send me all that.

I had probably a month to get through all of these docs. I appreciated that cuz then I could go back to something let it sink in.

The way I do it is by going through it and then writing out notes. I have a Google doc of my own notes that's private to me that I've had for years. It's probably thousands of pages long. I will say I very, very rarely go back and look at my notes. I do sometimes I have to do keyword find but I very rarely go back and look at it. But it's the act of reading and then actively taking a few notes helps things sink in a little more.

Every company has so many acronyms, and it's probably a really good thing because you need your own language and it adds to the culture. But learning them just takes a very long time. So for me, starting to see these acronyms and then open another doc and see the same one was helpful. And then maybe I'd talk to someone at the company before I joined and then go, wait, can you explain what that term is? And then, oh yeah, that's what this means. Oh, cool. Then I'd probably have to ask that again before I really remembered what it was.

But that process of indoctrinating myself into the language of the company early was really helpful because I was able to hit the ground running a little bit faster.

There will be a tendency for someone to want to take you through a doc, and that can be helpful. For me, I've found that it's easier for me to have read it first and then have someone take me because I'm more prepared. Of course, on the other side of that, if I'm someone trying to onboard someone, I'm usually like, oh, let me, let me share my narrative with you before you look at this on your own.

But as a consumer of it, I actually find the reverse is more helpful, which is, let me just look at it first. Even if I don't understand everything, that's okay because I'll be able to ask better questions. I'll understand some of it, and it'll prevent us from like going down rabbit holes that just aren't where we should spend live synchronous time.

My top tips for onboarding are:
One, you're never going to be as fresh eyed as you are at that moment when you're onboarding. There are a whole bunch of things that the company is doing for good reasons and a whole bunch of things the company is doing for bad reasons. So as a new person, don't assume everything that the company is doing, someone has thought through really well and has a good reason for doing it. Use that beginner's mindset to challenge those and. Soon you will be indoctrinated and you will think that is the normal way to do things, when in fact there's a better way to do it. Part of what we need out of every new person is improvement. But that can be scary because you're going against the grain. You want like fit in with all these new friends that you've met, and it's not always the best way to fit in with new friends by pointing out ways in which the things they're doing don't quite make sense. So I try to explicitly encourage people to do that. I actually will ask people to write down a list of things that don't seem right in their first few weeks to before they also become a boiled frog like the rest of us.

Second, I'd encourage them to prioritize spending time in the customer experience and understanding the customer's pain point and problem. Unfortunately, the customer is not in your meetings, your coworkers are. So if you're not intentional, you end up understanding your coworker's problems and your coworker's context, but you don't really understand the customer's problems.

One way I've seen people ramp in a wrong way is that they don't quite understand the complexities of the business yet order the customer yet, but they want to make decisions and have an impact. One way to feel like you're adding value is by doing something that changes the company in some way, small to big. But the danger is you don't have enough context to do that yet. So there's a balancing act: you want to come in and make an impact, but you don't have enough context to actually know how to do that yet. How do you temper yourself?

One of the things that I've tried to do and I try to encourage others to do is go ahead and do that. Go all the way through and try to make a decision, but don't make the decision. Go and tell someone. Your onboarding buddy, your boss, someone else who you respect at the company. Say, "this is the decision I would make given all the context that I have. Where do you think I'm wrong?" And let them say, no, actually I think you got it all. You're totally right. Or they say have you thought about these three things?
And that's a fantastic way to learn because you didn't just push the decision or everything off onto someone else to make, you tried to go as far as you could yourself but then you didn't go all the way because you don't even know what blind spots you have. So then you ask someone else to try to point out the blind spots, which then helps you learn even more.

Tom Willerer

I used this doc while preparing to join Opendoor as CPO. This artifact can serve as a guide for getting up to speed in a new executive role, including setting 90 and 180-day OKRs.

Welcome to Opendoor! We’re so excited for you to 

. Here’s some information that should help you get up to speed. Don’t hesitate to reach out to Eric, Andrew or Phatch if you have any questions.

Clare will be your interim Executive Assistant your first 1-2 weeks. She’ll meet with you on your first day to help design the best onboarding calendar for you.


1:1s (E-Team, Directs, Members of S-Team)

1:1s (E-Team, Directs, Members of S-Team) // E-Team Offsite

1:1s (E-Team, Directs, Members of S-Team) // Product Demos

Trip to PHX for CX, Homes, Pricing deep dives

In general, we try to live and breathe these values everyday, especially in all of our hiring and promotions

Drafted over the past month or so, this has been a northstar to ensure we’re resourced and aligned appropriately.

Note: You will need to enter your email address and it will require Okta authentication. 

Our central internal repository for company/employee info

Of late, we’re investing heavily in holding more events and driving more internal communications. Here is the latest, managed by X.

Our Senior Leadership Team, or S-Team, is comprised of some of our top leaders and areas of focus at the company (effectively one layer down from the E-Team.) We meet with this group on a monthly basis, and often hold strategic and/or social offsites with them.

You’ll find that Opendoor is quite jargon-rich :-) Here is a guide to all of the acronyms to help you get up to speed.

At the start of Q3, we held an onsite with all of the EPODs to discuss H2 plans.

In general, we’ve mixed presenting company OKRs and emailing them to the company. We decided to share both Q3 and Q4 OKRs in one communication this quarter.

You’ll find all of our Board decks here. Most of the 2020 schedule is still being fleshed out, but here are all of the past decks.

The executive dashboard packet that is reviewed bi-weekly by E-Team (Eric’s Executive Team)

Opendoor’s internal analytics portal, generally used by most of our employees.

This is a comprehensive overview of the design team, key initiatives, etc.

Also, here is a doc that Paul put together in terms of ensuring we are all driving towards deadlines -

This is an overview of the Seller Experience team and key planning and initiatives.

Our Head of Comms will include internal/external details for your hiring announcement here.

Secure exclusive with TechCrunch (will be good for recruiting). Need to determine date to announce. Was thinking one week after the start date.

**Please do not update any public profiles like Linkedin or Twitter until we announce.

Linkedin or Medium post from Tom re: why you joined OD and what you will be doing (for discussion)

Sept 3 (first day) - Welcome note on Slack from Eric

Sept 11 - Participate in EPOD Q&A (TBD on activity)

Build the product and design function and craft here at Opendoor, defining our operating principles and values

Build our mentorship program, implement consistent and clear levels, define what greatness looks like, and set the expectations on how to achieve greatness


Recruit and onboard exceptional leaders and/or ICs

Coach and motivate exceptional leaders and/or ICs

Manages with both metrics and vision, with a very high quality bar

Ability to assess talent and coach underperformance and develop stars

Ensures other teams are properly resourced and initiatives that impact KPIs across teams is optimized


Deeply understand and can explain drivers / correct them

Achieves results with repeatable mechanisms, not just heroics (led, not silver, bullets)

Partner to executives on all strategic matters

Be a critical member of a team working through high priority/”house under fire” situations

Develop a system and culture within product (and the wider company) to understand the core customers for the products being built, so that we can empathize with them and be inspired to build a product that delights them.

Build our mission to metrics, partnering to develop our product roadmap and product strategy

See around corners and help identify where there may be potential issues and exploit potential opportunities

Identify areas of inefficiencies and opportunities to move the business and customer experience forward

Identify highest impact initiatives for the company

Have an in-depth understanding of the customer experience and drivers of the business


Understand, live-out, and contribute to the overall culture of Opendoor

Build a culture of curiosity toward the overall business and other functions within product

Objective: Deeply understand the business from the strategy to the experience to operations

KR: Be well versed on all things Opendoor

KR: 1:1s with every major business and technology

KR: Read all major research on key customers. Where it doesn’t exist, create it.

Objective: Build a world-class product function

KR: Identify talent gaps in the current org

KR: Create a hiring and team editing / coaching plan to address talent gaps


Objective: Build a world-class operating and execution machine

New CPO Onboarding Document at Opendoor

Onboarding Doc: CPO, Opendoor

Suggested Ramp Up Meetings

Links to check out

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