ChatOps! Or, How I Learned to Stop Worrying and Love the 'Bot

I hope that when future historians look back on October 18th, 2013, they do not identify it as the start of the robot apocalypse.

On that date, I made the initial commit for Fashionator, Rent the Runway's Hubot instance. Until then, most of the communication from machine to human at RTR had been done via e-mail: service alerts, Nagios, Airbrake, and so on. We did have PagerDuty, but rather than having accounts for everyone, we had one shared account tied to a physical on-call iPhone. It was pink. I was led to believe it had been dropped in the toilet at least once. It was so noisy that most people turned off the ringer and just kept an eye on the deluge of e-mail devastating the inbox. I was not a fan.

To be clear: I didn't initially create our robot to solve this problem. Fashionator was born the way all Hubots are born, with community scripts to spam people in your company chat with animated GIFs clipped from '80s cartoons or pictures of put-upon looking pugs donning dollar store Halloween costumes. I figured the robot would be a welcome diversion from our fires rather than a tool to help extinguish them.

I don't remember the first useful script I added—it might have been one that checked Heroku's status, since we used to host some of our Sinatra applications there—but I remember the moment when people began to think of Fashionator as a productivity tool instead of as a distraction. A member of our product team asked one of the engineers to flush caches in the storefront stage environment. I said, "Fashionator can do that," and asked the robot to flush Memcached, which she did.

HipChat exploded. "I had no idea she could do that!" "What else can she do?" Pull requests started coming into the Fashionator repo over the next several days, and at our next hack day, I volunteered to help people hack on Hubot. Over several more hack days, scripts to automatically handle stage orders, query the PagerDuty API, write JIRA tickets, and deploy our WWW site to QA and stage environments appeared. We put her under Puppet's control and gave her her own Jenkins deploy pipeline.

The benefits of maintaining Fashionator have been surprising and tremendous. The centralization of communication afforded by having her in HipChat, where most of us spend our day anyway, means that we see alerts and deploy announcements immediately; if there's an incident, we can gather in our war room and ask if there are problems with GitHub, find out who's on call, search JIRA tickets if we suspect a recent change has broken something, and more. Fashionator also increases transparency and accountability, since everyone can see (or review in HipChat logs) what she's doing and who asked her to do it. Improved communication facilitated by our Hubot has made us better at everything from identifying and fixing bugs to onboarding, and with API integration with GitHub, Jenkins, JIRA, PagerDuty, and more, we're constantly making it faster and easier to share knowledge and get things done.

There are, of course, still times when she's bad:

But Fashionator has become an integral part of our lives at Rent the Runway, and we couldn't imagine working without her.

If you'd like to download your own Hubot, you can find instructions here and a repository of community scripts here.

Bridging the Design-Development Divide

As a user experience designer (and occasional developer) at a tech startup, I’ve seen many different types of friction between designers and developers. Designs handed off to engineers may be missing critical functional or visual specifications, include patterns that diverge from existing styles, or specify things that are overly costly to implement. Code created from designs may change flows unexpectedly, stick to existing patterns when new ones are needed, or not deliver the pixel perfection that designers expect.

When our team began work on a rebrand, I was focused on keeping these issues to a minimum. How could we communicate effectively to see a new look and feel come to life?

Initially, it was an easy sell to convince the design and tech teams that we needed a style guide: a living document to keep us in sync on how to use our new styles.

On the design team, our challenge was to take a brand package and bring it to life in a consistent, cohesive way across our website, app, stores, and packaging. We knew that ultimately each designer could not start from scratch on every new project, but we wanted to give ourselves the time to let our imaginations run wild and play with the new visuals.

To do this, we held design hack days, where we cloistered the design team in a room, uninterrupted, to envision where this new direction could take us. After several days, we had dozens of beautiful new concepts, but we hadn’t figured out all the nitty gritty details, so we continued working individually to flesh out different touchpoints.

I brought the design team together to create the style guide. It started as a Sketch file, where I gathered common elements and left blanks for components we needed to add.

  An early Sketch file we deliberated over


An early Sketch file we deliberated over

As individual team members worked on different touchpoints, we met to hash out each component of the guide. How were we using fonts? Colors? What signified interaction? We debated details like inner shadow on inputs, button states, and font hierarchy; we worked as a team to agree on a set of visual and interactive styles that contained enough variety to serve our many needs, but no more. These styles filtered back into individual projects so designers stayed on the same page.

As the design team solidified the styles, I coded the guide and published it online. Then, I worked with our developers to make it more useful. I added SASS variables, HTML elements, and CSS classes for quick reference. I also added our designers’ descriptions of how to choose between styles and make design decisions for the site.

Swatches, names, hex codes, and SASS variables live together in our style guide

Swatches, names, hex codes, and SASS variables live together in our style guide

Although we had gotten buy in to create the style guide, there was a period of time where it felt like nothing visible was being accomplished. In a sense, this was true – we weren’t changing styles on the site until we settled on our guidelines. However, the payoff for having a guide soon became clear.

As designers worked on the rebrand, we avoided recreating the wheel on each page – we stuck to visual treatments and interactive patterns we had collaborated on. Since there were relatively few treatments, we were able to cut down the need for detailed specifications. We could tell a developer “this is a title” or “this is sage” and know that they had an easy reference to check against.

Styles reserved for editorial usage

Styles reserved for editorial usage

Our guide also streamlined work for our developers, who were newly empowered to take a first pass at design and make design decisions without always needing a designer. Our new styles were both more semantic and more consistent, so we were also able to cut down on bulky HTML and CSS.

On our office wall, there’s a poster imploring us to “Move fast and break things,” and I do love the attitude that we should always be pushing fearlessly forward and trying new things. That said, we shouldn’t only focus on tangible output.

To work well together as designers and developers, we need to be willing to invest time in communication – to learn what the other side really cares about, what they’re willing to compromise on, and how to express our point of view in a way they understand.

The style guide continues to evolve as a conversation between designers and developers. In our next iteration, we plan to tackle responsive font styles. I’m sure there will be plenty of debate about how things should work. Ultimately, I believe the upfront time will be worth it, that we’ll avoid friction and communication overhead to see a shinier product with the same effort.

When Defining Reality, Don't Forget To Deliver Hope

I had a great 1-1 with one of my tech leads today, who came by my office hours and asked me for advice on becoming a better manager. I gave my usual rambling reply to broad inquiries; we talked about making personal connections, reading a lot of blogs and books, experimenting with different ways of asking questions to get people to reveal their true interests to you, so that you can better help to nurture and serve those interests.

But then, at the end, I had a thought. I asked him, how often do you talk to your team about what the future is about? How well do you know what the future of your team should be like? Not the product roadmap, which is in the capable hands of an amazing product lead, but the technical future. How to think about building systems that are future-thinking, becoming a better team, writing better code.

"Not that often" he admitted.

So, I persisted. How often do you spend some time away from your keyboard, away from the internet, away from meetings, and think about what you think the future of your team should be, the areas that you could focus on, the big opportunities for growth?

Again, the answer was "Not that often."

This is not at all surprising, of course. When you work in an industry where you focus on building out technical skills and getting more things done for the first many years of your career, making that shift into management (really a career change) can lead to the temptation to focus on solving today's problems now. Solving today's problems well is probably how you ended up rising into a tech lead role, and we all know that there is never a shortage of problems.

But when you focus on nothing but today's problems, even if you are a great manager who does everything right, you are unlikely to motivate your team to greatness, or inspire the level of loyalty and passion that makes a team gel and prosper. You are missing the one thing that you cannot overcome with great management skills. You're missing leadership.

You can be the greatest manager in the world, but without leadership and vision, your team will not be truly sticky to you. 

Fortunately, leadership is not a skill you have to be born with. It just requires that you identify the future and articulate it. "Define reality, give hope." Too often first-time tech managers focus on reality. We're comfortable with reality, reality is our bread and butter. But the future? Painting a vision for the future, even the future 6 months out, is a risk. You may not be able to deliver on that future vision. It may not be the right thing to do when the time comes. Reacting to today is so easy, and trying to predict the future seems really hard

But there's a simple (note: not easy) secret to breaking that habit and creating a vision: practice. Get away from your keyboard. Force yourself to sit in an empty room with a whiteboard or a pen and paper and write some ideas down. Grab a colleague or two to brainstorm with if you need to, but do some of the work by yourself. Then start painting that future to your team. This is the most important thing you can do to become a truly well-rounded manager, and if you aren't doing it, block your calendar tomorrow and start.

This originally appeared on Camille's blog,

Analysis Paralysis

     I was unaware of this phrase until a friend and colleague mentioned it to me but I was well aware of the symptom.  So many options and choices where do I start?  I suppose I'll come back to it later or even start on a different project with a more obvious starting line.  I believe everyone at one time or another has come across this syndrome and it might have even hindered their production. 

     Personally, I get through this barrier using some other idioms.  I 'jump right in with both feet', 'throw everything at it and see what sticks' and 'move fast and break things'.  Hesitation only makes me think more and when beginning something, that might not be the best way.  Sure, a well thought out plan is great but rarely does anything in my experience end up exactly the way it was planned.

     I believe just knowing the phrase 'Analysis Paralysis' is the first step in conquering the problem.  At least now I have something to search for while I am avoiding what I really need to do...


As I write this, today is beach day @RenttheRunway (July 31, 2014).

What does that mean? It means our CEO Jenn Hyman (@Jenn_RTR), decided that the whole team deserved a day of “Mandatory Fun” at an awesome beach with tennis courts and a pool and the whole nine yards, on the company's dime.

A few days before that Jenn spontaneously ordered an ice cream truck to come to the office and give everyone free ice cream. We're not talking 10 people here - we’re talking about the whole, enough-to-fill-multiple-busses, RTR office.

A few days before that there was a Hawaiian style BBQ/Luau at our Dream Fulfillment Center in Jersey (where your dresses are shipped from).

You get the idea.

But lots of startups have occasional crazy fun surprises like that (right?). What's really telling about a company is the day-to-day. This blog is about life @RTR_tech, not RTR in general. Make no mistake: this is a tech organization and it’s an awesome one.

Let me tell you a story. It's going to be a bit scattered, and probably long-winded, but I think you'll like it.

I promise I'll mention some tech along the way.

A little more than a year ago, I was living with my family in Ann Arbor, MI where I had worked for about 13 years. Ann Arbor is an awesome little college town, but my wife wanted to move back to NY where she grew up. As a prerequisite, I wanted to make sure I found a job in NYC where I could truly be happy. This was more difficult than you might imagine.

I was looking for a small-ish, startup-ish, flexible, open-minded tech company with outstanding people.

I eventually discovered a large list of NYC companies of this ilk. Cruising down the list in alphabetical order, I eventually came to Rent the Runway.

"A fashion/e-commerce company?," I thought, "meh."  I passed right over it.

Fortunately, it didn't end there. The CTO of another company (whose selfless kindness I should have repaid long ago) reconnected me with RTR_tech via CTO Camille Fournier (@skamille) I had a phone call with her and was extremely impressed. The rest is history. I also spoke to Vijay (@vjsubr), head of Analytics, Jenn Hyman and various awesome members of the tech team and I was convinced.

One year later, I can tell you that this company is far from just a "fashion/e-commerce company" and is anything but "meh."

These people are awesome and humble. They learn from their mistakes and they learn fast. They actively seek feedback. They listen deeply. They really, honestly care about their teammates. They have created a culture of openness, idea sharing, risk-taking, fun, friendliness, honesty, continuous improvement, teaching and in-the-end, success. And they pay me to hang out with them all day!

What follows is just some of the awesome stuff I’ve had the pleasure of living with @RTR_tech.

First off, we use modern technology tempered with a good bit of wisdom that the “Shiny New Thing” is not always as awesome as it seems. The grass is not always greener on the other side. We’ve adopted a lean-and-mean, modern Java web service framework called Dropwizard. Not Node. Not Scala. Not Python. They're all cool, don't get me wrong, but Java is tried and true and way cooler than you might think if you just take the time to get to know it. :) Plus: Java 8! And cool stuff like @AutoValue. We're working hard to move our front end code to Backbone. There's some Ruby in the mix for good measure. Plus, have you seen what looks like? It's freaking beautiful! We work with awesome designers and we really care about making it not just work right, but also look great.

We have regular, weekly one-on-one meetings with managers, team leads and peers. These are not perfunctory tech status updates. In these meetings we talk openly about what's bugging us. We refine our goals and take steps towards achieving them. We work to carve out time for people to work on that open source contribution they've had in mind (making @AutoValue work with Hibernate perhaps). As a manager, one of my personal rules of thumb is that performance reviews should not contain any negative surprises (or only good surprises). I've learned to use this one-on-one time to make sure that's the case and that I'm guiding/teaching (and learning from!) my reports to avoid those negative surprises. Just a few days ago I was writing a performance review. When I really got into the meat of it, I realized that I had some new suggestions around goals the person could set, but that we hadn't talked about yet. Before I wrote those things into the review, I grabbed the person and talked through the suggestions. The next day, we had the Important Official Mid-Year Review meeting. I delivered my write-up, and watched the pride swell up in the individual. This is not to say there was no constructive feedback, but that that feedback had already been well established and internalized. That's how you do performance reviews. We do that here @RTR_tech. If you're on my team, you'll get a performance review like that. I really care - we really care - about our teammates as people. In the end, that's all we have. Java code is easy. People are hard. Help them refine and follow their goals. Help them thrive. Help them learn. Help us learn.

@RTR_tech we are a learning organization from top to bottom. As such we’re encouraged (by @skamille and others) to attend technical conferences. RTR_tech will send you to speak or just attend. And of course, @skamille, @markwunsch, and @OMGannaks held a panel discussion @RTR_teach - oops, @RTR_tech - about how to write successful conference presentation proposals, because… they're awesome.

Similarly, we do Drinks and Demos every Friday. This is our chance to share essentially whatever we want as engineers. Maybe it's @timx showing off the new RTR Unlimited product/feature his team just released or @ericqweinstein teaching us some new stuff about "The Rubies." It could be @CarloBarbara doing a case study of how to systematically debug a tough OutOfMemoryError, because, as @skamille says, "don't flail."

Speaking of "don't flail:" you can learn that and so much more by going to @skamille's weekly office hours and having a great discussion with her. I'm not exaggerating that every time you sit down to talk with her, you'll walk away having learned something or with a new perspective on something. She maintains these office hours as a way to remain accessible and keep the communication lines open despite the fact that our tech team is quite large and growing rapidly. How accessible? Our awesome intern Maude (@QcMaude - A Post Internship Look at RTR) has mentioned to me how great it is that she is able to openly talk to Camille as she would any other peer.

There are lots of big brains out there in the world though, and we can't send the entire tech team to the next “Edgy Tech Conference.” In order to fill that gap we bring in guest speakers from time to time. We’ve invited people like the creator of Backbone (@jashkenas) and (@mrb_bk), an engineer from Code Climate (which we use for JS/Ruby static analysis).

"What if," you say, "I get a crazy idea that I just want to try and I never have time to build it?" You'll have your chance! In the year I've been here, we've had a hack day, a (3-day) hack “week” and a full, five-day hack week the last week of August. On hack week you get to work on (more or less) whatever you want as long as it’s vaguely related to making RTR more awesome. Best of all, these hack week projects often turn into real, even huge, projects that alter the roadmap of the company! For example, on we have a feature where users can upload their own photos. Unfortunately, the quality of these photos varies wildly. What if we had a way to automatically give each photo a quality score so that we could show the higher quality photos more prominently? I happen to have a background in machine vision. For my first hack day project, I built a first cut of such an image quality metric. It was simple, but actually showed visible improvements. (In a nutshell, the metric gave preference to images with 1 or 2 faces and images that are overall brighter.) Another example? Our huge new feature, a whole new subscription-based rental model called RTR Unlimited, started life as a hack week project.

But wait! There's more! A recent new hire asked me if RTR_tech does anything with open source. Indeed, we do! For starters, we are committers and some of the main promoters of the aforementioned Dropwizard. We also have more than one OSS project that we produced internally: Alchemy for A/B testing and Conduit for simplifying the use of message queues. I'm certain these projects are just the beginning. In fact, it's worth noting that our internal software development process is modeled to a degree on open source development. We use pull requests for everything, no matter how small, and naturally, have awesome unit test coverage. This is a great way to develop and combines the best of OSS development with the benefits of being in an office right next to your teammates. For one thing, I have found pervasive code reviews to be an excellent way to spin up new people on company standards or languages that are entirely new to them. It really works and has allowed me to remove one worry from my list of "oh man, new person, so much to cover."

All of this sounds fantastic, but we’re a startup so we must be working like dogs, right?


We have unlimited vacation. Now I admit to being a bit (a lot) cynical. On joining RTR_tech, I assumed that "unlimited vacation" was code for "guilt-based vacation." I was wrong. This is simply not the case. People take lots of time off, myself included, and I haven't seen any guilt-tripping at all. Remember, we're talking about real people here. Awesome people. It turns out, we respect each others’ need for time off. When @MichelleWernick goes to Paris, we all get excited for her and people step up to help fill the gap in QA. When @skamille goes to Hawaii, we don't flood her inbox; we step up and exercise our latent CTO superpowers. When she gets back, there's Hawaiian candy on the kitchen counter and funny stories about emergency room visits.

In fact, it doesn't end with unlimited vacation. We have stellar work/life balance in general. @RTR_tech we understand that the trick is to anticipate, plan, and course-correct a project early. We work hard to avoid feature creep and instead focus on quality. We work smarter, not harder. In this way, we deliver awesome software without people freaking out at the last minute, having to put out fires, and working 12-hour days. Sure, we're not perfect at it, but we've had major successes and we believe in it. We're continuously improving. (How about a Drinks and Demos presentation about what went right and what went wrong in that last big project release? OK!) We embody this in other ways too: Unlimited vacation begets unlimited maternity leave. (I've seen it more than once! It happens! It works! All companies should do it!) And after your maternity leave, maybe you want to have your newborn brought by the office every day so you can take time to feed it. Of course! Who wouldn't allow that? I have a son and a wife. I get to go home and eat dinner with them and when I return to the office the next day, is still there and I get to do more cool work on it with my fantastic team! I'm more loyal for the stability it provides. I take the time to write a blog entry because of it, and I spend that much more energy recruiting the next awesome teammate because I love telling them about it! What if you don't have a family? What if you're young and unattached? RTR is in NYC! Go enjoy living in New York Effing City!

Did I mention we're encouraged to write articles for our tech blog? Perhaps you've seen said blog? These kind of things are literally listed in our quarterly tech team goals. "1) Ship feature X so we can rent some more dresses. 2) Post 6 tech blog entries."

OK, I promise I'm almost done gushing, but stick with me a bit longer. There's so many more cool things to tell you.

I had a new junior engineer start recently. I gave him a week or two to settle in before I gave him his first major task. Let me set the stage: we're nearing completion of some initial research that uses Python to do Markov Chain Monte Carlo simulation for parameter inference on a Bayesian Network. (To predict the future. NBD.) I asked New Guy to determine if it's viable for us to port that to Java for production use. (The answer, two weeks later, appears to be yes, if a bit inelegantly, via Yadas (Yada Yada Yadas). So that's a thing we do @RTR_tech. Rad, right?

Our interview process is an area we've recently been working to improve (because we're doing lots of it). So how are we doing? Yesterday, I got overwhelmingly positive feedback from a new hire. He thought that it was fantastic to have an RTR_tech engineer guiding him through the whole interview process, answering his questions, being open, honest and enthusiastic. Shortly thereafter, he took the gig. Sounds like it's working!

Did you notice that I used one or two (or forty-two) Twitter handles here? That's because I'd love for you to join our conversation! I want to hear from you! What are we missing? What more can we do? To my fellow RTR_tech-ers (is that a thing?): what is life @RTR_tech to you? Follow us on Twitter @RTR_tech! But don't stop there! Connect with these awesome people about awesome stuff: @skamille, @ericqweinstein, @markwunsch, @bhsdrew, @CarloBarbara, @timx, and many more (use transitive closure to find everyone!)….

This is life @RTR_tech.

P.S. - I really wanted to figure out how I could work in a joke about Talk Like A Pirate Day being a big deal at RTR, but, as any good engineer knows, sometimes you have to kill your little darlings.