Zillow

1. Great and friendly people.
2. Clearly defined project and well executed.
3. Great executive leadership, clear roadmap on what they are doing.
4. Schedule is reasonable and not aggressive.
5. Easy problem to solve if you like it.

The following cons are from an engineering/eng-management prospective and may not be related to other orgs:

1. Engineering talent/leadership is not top-level. If you are a top-ranked engineer, you will feel a lot of pushback and dragging. Great ideas are not easy to spark.

2. Mid-management is very laid-back. They need to be more aggressive to help the company move in the right direction.

3. Granted, long-staying people are now at the mid-senior management level. However, this is a problem that prevents the company from moving forward. They have a lot of legacy issues that should have been fixed long ago if there was a commitment to it. Unfortunately, the safe route is always selected.

4. A lot of cost optimization can be done within the technical stack, but it is hard to convince people to care.

5. Technology management/development is traditional. You will see a bunch of Unix admins/DBAs and ops, handling day-to-day operations and also blocking progress in a SOA world.

I understand many companies have similar problems. Zillow is probably better than all of its peers, but given Zillow is young and wants to move to the next stage, then it has to do something different.

1. Keep up the good work defining clear goals!

2. More aggressively invest into R&D. I can see the ROI will be much better than flooding the sales org in the longer term, and more scalable.

3. Hire top-level talents and put them in charge; magic will happen. Focus on quality rather than quantity in tech talent hiring.

4. Hire technical management talent from top companies (FB/AMZN/GOOG) and transform the development process within Zillow. It may only need half of the developers to do the same job, yet yielding much faster iteration and better products.