Redmond to Redfin to Monde

In April 2007 I left Redmond-based Microsoft to join Redfin.  Before leaving, I wrote a little tribute to my time at Microsoft, listing the things I liked and didn’t like about the 5 years I spent there.

In a few days I will be leaving Redfin, and this time it’s not to join another company but rather to travel around the world for the next year with my wife Pnina.  My departure from Redfin is a temporary one as I have every intention to return to Redfin when we come back from the trip.  Nonetheless, this seems like a good time to reflect on my 1.5 years at Redfin, the things I liked and didn’t like, and how it all compares to my time at Microsoft.  Here goes.

First the good stuff…


Redfin definitely feels smaller and more agile.  We release new “major” versions of the website roughly every 2 months, and numerous “dot releases” in between, so you get to see the fruits of your labor more often.  You also get feedback more frequently and more directly.  By comparison, my former team (Virtual Earth), which moves pretty fast by Microsoft terms, generally released every 4+ months.  And the team before that (SQL Server) had a multi-year release cycle.

Proximity to Customers / Customer Focus

At Microsoft I was several levels removed from actual end users.  At Redfin I see emails from our customers on a daily basis, and often I’m called upon to help solve those issues and to be in touch with the customers directly.  As an extreme example, in the summer of 2007 when the TV show 60 Minutes aired a segment about Redfin, it was “all hands on deck” – engineering folks, like me, sat side-by-side with real estate agents as we all answered the flood of phone calls late into the night.

And we’re not just closer to our customers, we really care about them.  When we have our twice-monthly company meetings we always go over certain stats: we always look at profits/losses in each market, we always look at website traffic, and, most importantly, we always look at customer satisfaction (CSAT).  We measure CSAT using a metric called net promoter score, which indicates the degree to which our customers are likely to encourage their friends and family to also use our service.  The metric itself isn’t as important as the fact that we’re constantly measuring and trying to improve CSAT.  Similarly, when customers contact us for technical help (e.g. by emailing TechSupport (at), we always respond.  The responses generally come within 24 hours and always from one of us devs/pm’s/testers, not from some random call center in who-knows-where.  We do surveys and focus groups, red carpet events and open houses.  We’re constantly working to do what’s best for our customers.  Our philosophy is to spend very little a “customer acquisition” (AKA advertising); we figure if our customers are insanely happy, they’ll drive more customers to us.


Glenn (CEO) has developed a culture of transparency in the company.  It affects how we do business with our customers: we try to show as much information about homes for sale on our website as we can, and we don’t hide any details about the revenue we receive from each transaction.  It also affects how we do business in other ways.  It surprised me to see Glenn blogging publicly about our financial model, about our occasional screw-ups, or about his fear of inciting riots if he were to forbid us engineers from using Yammer.  It also surprised me to see the degree to which our execs are willing to share the financial state of the company in our all-hands meetings, down to some pretty detailed numbers – they trust us to be responsible with this data.  It took me a while to get used to this level of openness; it really was a kind of culture shock.

Career Growth

I definitely grew as an engineer more quickly at Redfin than I would have by staying at Microsoft another 1.5 years.  Part of the reason is that I was exposed to the world of startups and to a whole set of non-Microsoft technologies (Linux, Java, Eclipse, etc.).  But another reason is that in a smaller company you are naturally asked to “wear more hats” – to do whatever needs to be done, regardless of whether it’s in your job description.  As an example, at Microsoft I wrote software but relied on other people to actually package it or deploy it to production, whereas at Redfin I’m regularly involved in managing deployments.  In addition, at Redfin I was able to step into a lead position just a few months after joining the company.

Seriously Hard-Working People

I don’t mean to imply that at Microsoft people don’t work hard.  But I can say without hesitation that I never worked as hard in my life as in the first few months after joining Redfin (when I was ramping up) and several times since.  And I don’t think I’m the hardest working person at Redfin, not by a long shot.  Our Real Estate agents are maniacs – you have to be in order to complete 10x the number of deals in a year that a typical agent does.

Worth noting also is that Redfin takes the mantra “hire slowly and fire fast” very seriously.  At Microsoft I didn’t actually know anyone who was let go of their job – I only heard stories (like that one guy who made money on the side by selling company-store software in the Fred Meyer parking lot, and then created a website to show off “the house”, “the cars”, and “the women” he got with his fortune).  The general consensus at Microsoft was that you have to work pretty hard at getting fired.  I don’t mean to say that people regularly took advantage of that, but I do think that at a big company you can choose to sit back once in a while.  Not so at Redfin.  In just my 1.5 years here I’ve seen several people let go.  It’s never a fun thing and we don’t feel good about it, not least because we’re all partly responsible when an employee doesn’t succeed.  But Redfin doesn’t dance around the issue – it takes action.

On the hiring side, Microsoft has the luxury of a huge pipeline of incoming resumes (and the corresponding headache of sifting through them).  Redfin has a far more modest share of incoming resumes.  And our hiring bar is high, likely higher than at Microsoft, which in turn means that we hire very very slowly.  During most of my 1.5 years at Redfin we tried to find another developer to join my team and we never found a match (until just now – luckily we found a good replacement for me; welcome Dave!).

OK, now for the stuff that could be better…

Less Long Term Planning / More Randomization

Because we’re so agile, we don’t spend as much time on the long-term plans and we often change even our short-term plans.  Of course, in many ways this is a good thing – we’re a startup so we need to learn and evolve rapidly in order to compete.  But as a downside, when you look at our codebase you find traces of various efforts that we started implementing but didn’t quite finish, things that we never fully cleaned up.  I was really surprised by this – I actually found more “legacy” code at Redfin than I did at all of my projects at Microsoft (my case at Microsoft was unique as I mostly worked on new projects, but still).  I think our CTO, Mike Young, does a pretty good job of giving us time for cleanup/refactoring efforts, but of course it’s a balancing act – you have to weigh time spent on infrastructure against time for new features, and when you have competitors that are also moving fast, it’s not an easy call.

More Passionate People = More Stubborn Disagreements

People are extremely passionate at Redfin.  Of course this is mostly a good thing – you need people who really care about making the startup succeed.  But as a side effect, passionate people are less likely to give up a fight when they disagree with you.  And since there are a million ways to skin a cat when developing software, this means that you are more likely to butt heads with other engineers at Redfin than you would at Microsoft (at least that’s what I noticed).  BTW, I don’t mean to say that this happens every day and I don’t mean to say that I dislike my fellow Redfin engineers – I have the highest respect for them.

Fewer Resources

There are benefits you find at a big company that you simply can’t find at a small company.  At Microsoft I could open the http://mste website and look up which interesting lectures are happening today around campus.  At Redfin we occasionally do brown bag talks (and often they’re pretty good), but it’s just not the same scale.  Also, at Microsoft if I ran into an issue with some technology, I could often look up the owner and give them a call (or even walk to their office).  At Redfin we use lots of open source technologies and the documentation/support is oftentimes sketchy (though, again, sometimes it’s surprisingly good).  We have to rely on ourselves a little more.

Modest Benefits

I hesitate to say this because Redfin’s benefits aren’t necessarily worse, just different.  Microsoft definitely has the edge when it comes to health insurance – no debate there.  Also, after a few years at Microsoft I had a nice steady income with stock grants vesting every year.  I took a bit of a hit in terms of income when I came to Redfin, but of course I also have stock options and if/when the company succeeds, they will be worth a lot – it’s a startup so that’s the tradeoff.  Also, we have various smaller perks like catered lunches three times a week, but we don’t have a health club membership.


There’s a non-zero chance that Redfin won’t be there by the time I return from the trip.  Do I really think it’ll fail?  No.  There are way too many positive signs, even in light of the back-to-back whammies we’ve faced recently – first a falling real-estate market and then a falling mortgage market.  We’re small and scrappy, our customers love us, and the real-estate pie is gigantic so there’s a lot of room to grow.  Still, it could happen.  You have to accept this kind of risk in order to get a shot at the excitement that comes when you create something new and radical and beautiful.

So there you have it.

I guess the natural question to ask is: “Are you glad you chose to switch to Redfin?”  Absolutely.  The main reason is that I feel I learned more and advanced my career much faster at Redfin than I would have by staying at Microsoft.  Would I work at Microsoft again in the future?  Definitely – it’s still a great company and I still feel pride when I see my old teams release new versions of their products.


7 responses to “Redmond to Redfin to Monde

  1. Pingback: The Best Blog Post About Redfin | Redfin Corporate Blog

  2. Shahaf, you da man. I hope you have a great time traveling. I wish I could be there with you. Working with you at Redfin was a pleasure (though bowling with you was more fun!)


  3. So, Shafah – who would you rather wrestle – Savan or me?

  4. I’d rather wrestle Janelle .

  5. Pingback: » links for 2008-09-30

  6. Shahaf, Great entry!

  7. sorry to have missed you guys last nite, but i have a feeling i’ll be running into you and pnina somewhere soon! have a GREAT time, see ya when you get back!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s