Mike Isaac

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Twitter Untangles Its Overgrown Org Chart

twitter_engineeringTwitter isn’t such a little bird anymore. The company has ballooned in a short time, adding more than 1,000 employees to its ranks in the span of just one year.

And like any company going through a growth spurt, Twitter’s organizational structure has become complicated.

The company has tried breaking into multiple departments with various leaders. But as time has passed and Twitter has scaled, roles have grown confused and inefficient, and communication between some of the departments has suffered.

This is important. Some say the company thrived in its early days from its loose-knit structure, but also suffered from a clashing of big personalities, a revolving CEO seat and defecting employees across the ranks. But as the company continues its slow, steady trudge toward going public, the Twitter of today is trying to be a different animal entirely. That means working out the kinks that still exist inside its organizational makeup, and proving to the public — and the Street — that yes, Twitter is in this for the long haul.

Making this adjustment will also mean clarifying the vision of what Twitter, the product, is, and what it is meant to be. That means faster shipping of new releases, faster decisions being made, and ultimately (hopefully), a happier user base.

To remedy the most recent issues, Twitter made significant structural changes to a number of departments earlier this month, shuffling around key managers in the hope of streamlining some of the more dysfunctional aspects of the company’s interdepartmental communication.

This is likely a good thing — or Twitter wants it to be, at least. But looking back, one thing is clear: It has been a long time coming.

Twitter, not unexpectedly, declined to comment on this story.

The Old Guard

This whole thing began nearly a year and a half ago, when CEO Dick Costolo and Chairman Jack Dorsey started cherry-picking talent from some of the Valley’s top firms. They plucked away Google engineers by the handful, recruiting hundreds of them to staff Twitter’s large engineering operations (Costolo has said more than half of Twitter is made up of engineers).

The idea back then was to restaff some of the key positions in the company with seasoned vets across the four major departments — Product, Design, Engineering and Revenue — the heads of which would report directly to Costolo.

Twitter Product VP Michael Sippey

Twitter Product VP Michael Sippey

But the old layout, as it was set up, was complicated. Former SAY Media vet Michael Sippey led as VP of consumer product development, while Othman Laraki was VP of product growth. Revenue had Adam Bain as president of global revenue, with Kevin Weil as his deputy of sorts, acting as director of revenue product. Design was led by Doug Bowman, but then Andrei Herasimchuk was promoted later to become overall director of design, while Bowman continued as creative director.

Lastly, Adam Messinger was poached from Oracle to join as VP of engineering infrastructure in November of 2011, while Chris Fry was brought on in April of 2012 for another key engineering role.

So that was the lay of the land. Costolo had his lieutenants, who ideally would handle things smoothly and hand up the high-level stuff to the top. But as became evident shortly thereafter, that didn’t work out.

It’s Complicated

First of all, it’s tough to have too many cooks in the kitchen. And despite the fact that this layout seemed to be streamlined, there were too many people reporting to Costolo at any given time.

As one insider told me, “This was a mess. One year ago, Dick had four product and design reports and three engineering reports.” In other words, seven different department heads, each with Costolo’s ear.

Beyond that, there were some issues inside of a few departments that contributed to stumbles in workflow.


The Design department has been dysfunctional for a long time. Earlier days saw an “overall lack of process and structure,” another person told me, and a series of new managers may have been an overcorrection, from Doug Bowman to a period with Dorsey’s heavy involvement, then to Andrei Herasimchuk after his promotion.

Design VP Mike Davidson.

Design VP Mike Davidson.

There were many issues involving the shifting of styles from Bowman to Herasimchuk. “Dick gave the reins to Andrei because he needed Design to move forward and [Andrei] is a driver,” another source said. That meant an increased, rigorous focus on the process, markedly different from what the team was used to with Bowman. But some in the Design department would still occasionally go to Bowman instead of Herasimchuk, effectively screwing up the chain of command. “The two had serious issues with one another,” one source said.

Thus, Mike Davidson, a veteran designer who was founding CEO of Newsvine (acquired by NBC), was picked last autumn by Sippey and Messinger to refocus the department. There have also been a series of smaller departures inside the department, and one big one — Andrei Herasimchuk left just a week after Davidson’s appointment.

I’ve been told by multiple people that the design process has improved significantly under Davidson’s reign over the past five-plus months, and he has brought in multiple new hires from the likes of Apple, Facebook and startup PicPlum. He has also increased the department size by 30 percent since his arrival.

What remains to be seen, however, is how much Davidson will improve the output of the overall department.


The Engineering department had its own problems. And the setup has been somewhat peculiar.

Adam Messinger was poached from Oracle to act as VP of infrastructure engineering in November of 2011. But at some point along the way, Messinger switched over from infrastructure to VP of application development — essentially a product position. That’s something of a head-scratcher, because Messinger’s background isn’t in consumer products, but infrastructure — the very thing he was hired on to do.

Twitter CTO Adam Messinger

Twitter CTO Adam Messinger

So in April of 2012, Messinger grabbed Chris Fry from Salesforce to head up infrastructure. But then Fry, too, found his way into working on consumer-side applications. Makes sense, as that’s part of Fry’s background, but it still got a bit wonky.

Through all of this, Design was reporting to the Engineering department instead of acting as an independent function as it once used to.

Everything Old Is New Again

So despite Twitter’s grand organizational plan set out last year, things weren’t working out. Design reporting to Engineering just wasn’t working. Engineering leadership was muddled. Costolo had too many people to listen to in order to get things done. As one insider told me, it was “a mess.”

So as of mid-March, there’s a new New World Order at Twitter, a long-overdue “consolidation and clarity in the company,” as one source put it.

Now, according to sources, the structure has been trimmed down to a handful of go-to VPs reporting to Costolo, including Michael Sippey, Chris Fry, Kevin Weil and global revenue president Adam Bain.

Sippey is getting the biggest bump. Laraki left Twitter at the end of 2012 to work on his own thing. Sippey is now vice president of Product and Design, overseeing both departments.

Senior Vice President of Engineering Chris Fry

Senior Vice President of Engineering Chris Fry

Design now reports to Product. While Davidson will continue to act as VP of Design, I’m told having Sippey in charge overall is a better situation for Costolo; if there are disagreements between departments, Costolo won’t be required to step in and arbitrate. Plus, Sippey and Costolo have known one another for quite some time and work well together.

Fry also gets a radical step up in his responsibilities. He’s now senior vice president of overall engineering. He’ll also work closely with Alex Roetter, who is now a VP in the Engineering department, working on international, growth and revenue engineering. Kevin Weil will continue to act as director of product in the revenue department.

Messinger is the man spun off here, announced last week as chief technical officer of Twitter. It’s curious, though; sources said that in his new position, Messinger lost many — if not all — of the staff directly reporting to him, which would make it seem a less-than-desirable position to be in. I’m also told that Messinger had issues with recruiting enough engineers, a serious problem at an organization of Twitter’s size and scale. Recruiting, as any tech company will tell you, is of the utmost importance.

Of course, it could be that Messinger is better as a high-level thinker, as I’ve been told — someone who would do better focusing on the “big-picture” aspects of Twitter and what it will look like in the future, rather than down in the engineering trenches. Still, perhaps Messinger won’t be satisfied with the high-level CTO role in a few months, and depart for other pastures. (TBD on that one.)

To Be Continued

So that’s that. For now, most of the shifting is kaput (as far as I’m aware), and as it has been put to me, the Sippey/Fry combo is the “new world order in charge of the roadmap,” while Weil and Roetter will hold down the revenue product and engineering duties. (There were one or two other noteworthy shifts as well, including moving Raffi Krikorian up to VP of engineering in charge of Twitter’s platform.)

If all goes according to plan, you’ll hopefully see Twitter-the-product get better on a much faster-paced timetable.

Will it all work better than the previous layout? I don’t know, and I’m sure Twitter doesn’t either. We’ll have to check back in another year.

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Another gadget you don’t really need. Will not work once you get it home. New model out in 4 weeks. Battery life is too short to be of any use.

— From the fact sheet for a fake product entitled Useless Plasticbox 1.2 (an actual empty plastic box) placed in L.A.-area Best Buy stores by an artist called Plastic Jesus