Transitions (continued)

Three years ago (almost to the day), I wrote a blog post titled Transitions that talked about transitions going on at our portfolio company Etsy. At the time, Etsy's founder Rob Kalin was handing over the CEO job to Maria Thomas, Chad Dickerson was coming in to run engineering, and founders Chris, Haim, and Jared were leaving the company to do other things.

And now, three years later, the actors in this transition story continue to evolve their roles. Chad—whose leadership in engineering has turned Etsy into the premier web technology company to work for in NYC—is taking the lead role as CEO from Rob, who is once again transitioning out of the day-to-day management. 

Being a founder of a highly successful company is thrilling but also a somewhat harrowing role. As the company scales, things change. Nothing happens as fast as it did when you first built the product. A minor feature rollout takes longer than it took to build the entire website. Nobody cares as much as you do about the sign on the door, the company employee directory, the brand, the copy on a marketing document, the place the checkbox is on the page, etc., etc. And yet, when there are hundreds of employees, you have to rely on all of them to do all of these things. It's a struggle for every founder I have ever worked with. And Rob is so very much that founder who cares intensely. He has given so much to the company over the years and he just completed a product roadmap that provides a guidepost for what Etsy will become in the coming years. As Rob transitions out once again, I want to personally thank him for all of this and more. Etsy is his creation and will always be.

Transitions are never easy on the people involved and the company that goes through them. But they are inevitable in any company's evolution. Some of them work out well and others not as much. But the role of the management and Board is to constantly try to have the right people in the right roles at the right time. And I think we've got that at Etsy now and I'm excited to see Chad step up to the top job and lead the company forward.


Comments (Archived):

  1. matthughes

    The trajectory of a successful startup is amazing. 0 – 60 with no letting up.It must be nice to step ‘aside’ for a moment and not be the one that is entirely responsible for making sure it stays at 60…

  2. Carl J. Mistlebauer

    I have watched Etsy and Storeny with interest for quite sometime; without any clue about the behind the scene people or activity I have to say their evolution has been exciting to observe.I also have to acknowledge that “founders” mentality today is totally different than that a generation ago; now they play to win, to succeed, and to do their best but they think as “teams” rather than individuals; its winning that matters not who scores the winning point.  That does give companies today the advantage over companies in the old economy world.  A true leader knows when they must step out of a situation, they know when they have to turn things over to others.Over the last 25 years I have watched lots of companies come and go, and I can look back now and pinpoint their demise to a time where the owner/founder had to make a call, had to step back, or step out, had to accept the fact that the product and or company was greater then they were, was more important than they were, those who could accept that succeeded and those that couldn’t failed…. 

  3. Oliver Hurst-Hiller

    Chad is awesome! I am an unabashed fanboy.  🙂

    1. Luke Melia


  4. Jon Williams

    Chad rocks. Another Chad fan…

  5. Tarikh Korula

    I met Chad at Yahoo’s first open Hackday and have been a fan ever since. Sad to see Rob go, but I’m sure Chad of all people can steer Etsy through its next growth phase. He’s created an incredible engineering team there. Go Etsy!

  6. johnmccarthy

    Great move.

  7. harryh

    > whose leadership in engineering has turned Etsy into the premier web> technology company to work for in NYC*ahem*;-)

    1. RichardF


    2. fredwilson

      When you add 60 engineers in a year (this year?) I will take that back harry

      1. harryh

        Gauntlet thrown!

      2. Watching the Wheels

        And when I begin to see an uptick in my views, I might even be impressed.

  8. markjosephson

    I remember meeting Chad back in Etsy’s old offices when he just started.  Great to see the dedication and passion survive.  Also love to see a great CTO become a great CEO.  Not the typical path, but a great one.  Great move.

  9. ShanaC

    Good luck from a customer!

  10. William Mougayar

    In the corporate world, they call this “succession planning”. It’s a fancier word than Transitions, but accomplishes the same thing.

  11. Donna Brewington White

    Decisions like this give clues as to the stuff a company (or its board) is made of.  Takes clarity, courage and wisdom to make these types of decisions.  

  12. devi

    <quote>..Chris, Haim, and Jared were leaving the company to do other things.</quote>***I think, this is the first time I read officially (= from an insider), that Jared left Etsy.  I’ve suspected it, but never had any proof. There were no announcement about this, other admins said no and his photo is still to be found on the “About” page. Sad.

  13. Robert Thuston

    Rob built Etsy by being obsessive over the direction, design, and philosophy behind the product.  I imagine it is difficult to transition from that to guiding people to be the instruments in the process.I’m curious as to how it is done.

    1. Dick Cheney

      he somewhat had problems working with his original team, too…> One day, Maguire recalls, Kalin proposed creating a system whereby sellers could broadcast live video feeds from their workshops. Another day, he was pitching his co-founders on creating a modern-day version of guilds. “There would be a brand-new idea every day,” Maguire says. “Usually it’d be something that didn’t even make sense. How are you supposed to teach blacksmithing over the Internet?” By the end of 2008, Maguire and Schoppik left the company. Working at Etsy, he says, “was like being in an abusive relationship.”…

      1. fredwilson

        you will never hear a negative word about Rob from me

      2. Robert Thuston

        I’d rather work for a boss, like Rob, that’s customer focused and mission-driven, than a boss whose purpose is to make a profit.

      3. BFillmore

        Selling on Etsy is where the real abuse is felt.Resellers taking over, front page favoritism, permanently muting long standing members of what once was the community, and treating sellers like unpaid employees instead of those that form Etsy’s unique customer base, that is where Chad needs to begin his mission of greatness.Don’t believe me? Well start reading here:

  14. David Miller

    I can tell you how tough it is to transition out as a founder and a senior leader … I mentioned this before in a comment to a post on this blog in January ( and  It’s now seven months later and it’s still hard; I’m very gratified that the transition has gone smoothly and the company has done extremely well this year.Best of luck and congratulations to Rob.  He’s doesn’t probably realize how much the experience has changed him yet.  

    1. Robert Thuston

      Thanks for sharing.  I enjoyed that you documented the event in real time.”Life is too short not to pursue your dreams, and mine have always been about creating new things from scratch: things that didn’t exist before, things that people didn’t ask for, things that people don’t yet know they need.” Love it.

  15. Bryan J Wilson

    As others have said, this is never an easy decision for anyone involved. But putting myself in Rob’s shoes (if I may have that honor), I can only imagine how difficult it is to let go. In work and relationships, letting go when everything seems to have gone so well is gut wrenching. And despite others’ relative objectivity and all the smarts in the world, there’s nothing but time that can heal that wound. I’m confident Rob, Etsy, and their customers will all look back on this as a good, necessary move. But that doesn’t make it any easier when it actually happens. Thanks for sharing Fred!

  16. Dick Cheney

    I guess this means the recent additions to Etsy have not been successful? I’m not surprised, as I shuddered when you guys rolled Rob Kalin back out from his closet to replace Maria. What Etsy has done in the past year has been 35% good, 65% ridiculous. Hopefully the new management (Dickerson is an insider so not that new) will start listening to existing customers instead of pushing the most dedicated customers away. Closing the forums was an insult and destroyed some dedicated communities Etsy used to have. Odd that this was part of a push to be more ‘social’.Please don’t bring Kalin back again. Pretty much everyone that was around for his last reign of terror knew this would be a disaster. Why was this not more clear to the people running Etsy?

  17. sigmaalgebra

    “Nothing happens as fast as it did when you first built the product.  … etc., etc.  And yet, when there are hundreds of employees, you have to rely on all of them to do all of these things.”Yup.  Good management can improve these things, and bad management can make them worse, but they still happen.  If need “hundreds of employees” all closely involved with the core of the company, then have to accept some ‘big organization’ realities.So, right, there’s some wasted time and money.  Sometimes there’s fighting with a guy down the hall instead of competitors outside the building, various efforts at politics, etc.  A CEO needs a little experience with such things, with human nature, and with Organizational Behavior 101.But having “hundreds of employees” should be one heck of an advantage:  The founding CEO who “first built the product” should find at least a dozen people who, really, can make some good improvements on what the CEO did when he “first built the product”.E.g., I just got my most complicated Web page working.  It’s ‘dynamic’ and, thus, changes during usage.  I got each little part positioned within about 2 pixels of where I wanted it and, more importantly, learned how to do such positioning.  So far the page looks essentially the same in IE and FF.So, that is some success, and the page should be functional enough, but the page is no artistic masterpiece:  A good Web page designer and a good Web page programmer could do things quite a bit nicer.But worrying about a few pixels should not threaten the leadership of the company; the realities and responses for having “hundreds of employees” should be easy enough to understand, accept, and handle well enough not to cause CEO ‘transitions’.That the company has the funds for “hundreds of employees” is one heck of an accomplishment for the founder.I’ve seen some big organizations continue on where nearly everyone in management was, say, quite ordinary in their work as managers!The big issue is really at the top:  A CEO who really cares should be able to walk around and not have to hit people over the head to see if they are just asleep or really dead.If a CEO is having some fairly obvious problems, then some appropriate ‘consulting’ should be able to save the situation.Then”As Rob transitions out once again, I want to personally thank him for all of this and more.  Etsy is his creation and will always be.”sounds like something tragic just happened for all concerned. 

  18. Omniture User

    Transitions, and the change that comes with that, are indeed a vital part of any company, especially one that was born from the internet.I can only speak from my one experience through my 6 year tenure where I wore as many hats as one could possibly imagine, but the internet is not what it was then and it will definitely not be anywhere close to that in the future.Transition is good, and it should not signal that something dire is to come.  And from experience, I can only tell you that the worst thing for any company is the lack of transition, the lack of evolution and of change. At my place of employment, I could only wish for such an event to happen, but sadly I know that it is probably much too late. “But the role of the management and Board is to constantly try to have the right people in the right roles at the right time.”Unfortunately where I am at, the issue was in our management and our CEO (who is also the Chairman of the Board).  Fortune placed him in the right place at the right time as we rode the wave of exponential growth to our peak, and it has been nothing but downhill as we failed to evolve…to change…to transition.Now we are all watching as his creation is taking on water with no way to right the ship. And sadly, the victims, who include myself, will be the group of talented individuals that were never given the trust and empowerment from the CEO that didn’t want to change or listen to anyone who said we needed to push the envelope and evolve, much as the market has.Transitions are fantastic and it’s comforting to know that it can come from even the most successful companies who are looking to continue to grow their success even more. Hopefully my next role will be at such a place, even though where I live is not typically known as an origination of such daring, adventurous and lifestyle changing startups.

  19. Prokofy

    I actually finally bought something for my daughter on Etsy that she wanted because you yapped it up so much, I finally had to stop roaring at Regretsy and go and see if really there was anything on Etsy worth getting. Regretsy is really hilarious though. My daughter likes Etsy.Worked great, great system. Like ebay but without the auction pressure and the fees.