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Interview with Gentry Underwood (Orchestra)

Orchestra is an online social to-do list that brings chat and e-mail together.

I interviewed Gentry Underwood, Orchestra co-founder to find out more. This interview is the fifty second in a series of DW interviews. Big thank you to Gentry for the interview!

Describe Orchestra in under 50 words?

On the surface, Orchestra is a simple to-do list. But as you use it you discover it’s actually a powerful organization and collaboration system in disguise. Most to-do lists just taunt you with everything you need to do. We want to help you get stuff done.

What was your inspiration for starting to work on Orchestra?

I was at IDEO working on collaborative software systems and my co-founder was at Apple spending some of his time doing the same. We were both working in cultures where you couldn’t force people to use your product, even though the company would be more effective if everyone did. That meant we had to design tools that people actually *wanted* to use for their own personal reasons, in addition to whatever macro benefits the system might provide. As we traded best practices on designing for adoption, we began to imagine building a system of our own…

How did you come up with the name?

We locked onto the name “Orchestra” pretty early on – it felt like a powerful metaphor for a world where lots of people can more easily collaborate with one another. A world where everyone plays a part.

What was technically the most challenging part of developing Orchestra?

As soon as we started prototyping a social to-do list we discovered that we needed to build a real-time messaging system. People would expect delegation of tasks, and subsequent communication through comments, to just work. Orchestra has a world-class engineering team and everyone rallied around the challenge of building real-time sync system that would work seamlessly between users, whether they were on the web or on iPhones. Our goal was to be faster (and more reliable) than text messages, and we succeeded. It’s the sort of thing you only really notice when it’s broken, but without it the whole experience falls apart.

How long did it take to put together Orchestra?

We incorporated the company in November of 2010, and we had pulled a small founding team together along with some seed financing by March of the following year. After several initial prototypes we started working on what became our production system right around then. In September we launched our first public version of the product.

Congratulations on being selected as the Top Productivity App of 2011 by the App Store! Do you have any new features in the pipeline?

We continue to be honored by the reception of Orchestra. It’s humbling. We’re a team that believes strongly in a human-centered, iterative design process as the single best way to build something great. That takes time and iteration, though, and there’s so much more work ahead of us.

Already our users have taught us a ton about what they actually want/need in order to be more productive, and much of it was a complete surprise. We’ve got some really great stuff in store that’s a direct result of listening to feedback — stuff that simply hasn’t been done before. I’m really excited about the future.

Orchestra was also recently nominated for Best Design at the Crunchies Awards! Have you always been into software design?

Yeah, that was also a huge honor for us. We took the whole team to the ceremony, knowing full-well that we weren’t going to win a popular vote against the likes of Pinterest and Path. Seeing all these startup rock stars accept awards was really great experience — a rally call for the team. There are some absolutely incredible companies in the Valley right now.

Personally, I’ve been designing software most of my life. I had a job designing HR and business systems in Visual Basic back in High School for a telemarketing company (hey, you gotta start somewhere :) and coded up my own ideas in Pascal and QuickBASIC on the side. I ended up going to Stanford and majoring in HCI before working in the valley designing software during the first dot-com craze.

What do you wish you’d have known 5 years ago that you know now?

I wish I’d known how big the App Store was going to be. I was absolutely obsessed with the first iPhone and elated when Apple backed off the no-3rd-party-apps policy, but I didn’t think about how much of a first-mover advantage early apps were going to have. There are some absolutely dreadful pieces of software out there that have large user bases mostly because they got in the store early. Fortunately Apple makes it so easy to try new software that the there’s plenty of opportunity for disruption.

Where do you see Orchestra in 5 years time?

We’ve always dreamed of building a big business with Orchestra — something that puts a dent in the universe, if you’ll pardon the cliché. We think there’s so much inefficiency in matching needs with the people and services that can meet them, and we have big plans for taking out as much of that friction as possible.

Has Orchestra got the feedback and growth you expected since launch?

To be blunt, growth and feedback has vastly exceeded our expectations.

Who would you say is your biggest competitor?


What is the biggest hurdle you have faced or are still facing?

Hiring is challenging. The market for talent is tight, and we refuse to sacrifice long-term culture for short-term capacity, so we tend to be pretty picky about who we bring on. We’ve been exceedingly fortunate with the team that’s amassed so far, but we could use at least one more of nearly everybody :)

Who do you see as your target audience?

People who have more to do than time to do it.

What are you most excited about at the moment?

I think these magical little devices that we carry in our pockets are just plain incredible, but that we’re just seeing the beginning of what they’re capable of. Most of the apps out there replicate sit-at-your-desk software in a way that’s more tailored for a mobile UI. While that’s interesting (and important), we’re learning that the biggest opportunities lie in doing things that simply haven’t been possible before — things that leverage the fact that now we’re always connected by smart devices. I think that wave of innovation is just getting started.

Can you convince the reader to start using Orchestra in under 50 words?

To start using Orchestra now is to join us on a journey. We’re committed to building the best system in the world for getting things done, so you can devote more time to the stuff you love. Help us get there: try it out and send us your feedback. Thanks!

Finished reading? Check out Orchestra!

This entry was posted on Saturday, February 11th, 2012 at 12:35 pm GMT. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.

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