Square

Square

I'm an engineering manager for the popular payments service.

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A creative technologist who designs and develops websites.

Over ten years of experience for a lot of cool companies: Square, Gucci, Pocket and more.

Pocket

Pocket

I was the platform lead for this widely used save for later service.

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General Assembly

General Assembly

I taught front end web development and a self-designed responsive web design workshop to future developers, entrepreneurs and designers.

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Gucci

Gucci

I was the front end lead for all design and development on gucci.com, a global e-commerce fashion site.

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Latest Blog Posts

My rules for managing distributed engineers

One of the hardest learnings from managing distributed teams for several years is that there is no single “best” environment for everyone on the team. Offices will eventually reopen with every individual strategizing what comes next. Some can’t wait to be in a busy, humming office five days a week. Others are cutting the cord entirely, moving away from big cities, and going fully remote. Some prefer a mixture of several days of the week in an office, the rest elsewhere.

It’s a challenging situation because managerial decisions around work environments can favor some and upset others. So over the years of managing engineers all over the country and across multiple time zones, I’ve established three simple rules to set expectations around work. Obviously companies have their own policies, so consider these more idealized or preferred for when there’s flexibility:

  • For an engineer’s “core work” environment, we treat every individual as a full time remote employee.
  • Outside of core work, we acknowledge experiences will be different. We strive for empathy, not equality, for this aspect of the job.
  • As long as we equip individuals to do their best work, location, and in most cases time of day, is entirely up to them.
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Dynamic gaming with Genesis Noir and Observation

Even months removed from their initial play through, Genesis Noir and Observation have stuck with me. It’s not due to either game’s overall quality; both impress with plenty of initial style and swagger, only to narratively stumble in the final acts. Instead, it’s all about their daring approach to user interface and control scheme, both which change frequently throughout the story. The experiences I had with both games made me realize how thrilling it can be when gaming conventions are broken.

For most modern games, the UI and control setup remain consistent throughout the a playthrough. For example, in the most popular game genres today – first person shooters, third person action adventure, and sports – you use a controller’s analog sticks for movement and looking around. For shooter titles like Destiny 2 and the Call of Duty series, there are expected conventions on the HUD to show player health, ammo, and a mini map of the player’s surroundings.

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Staying organized with ticklers

Engineering managers get a high quantity and variety of inbound requests. At any point, you can be on the hook for the status of individual projects, career growth questions, support issues, and more. Questions and expected follow-ups can pop up in many contexts, be it 1:1s with reports, standups, or cross functional meetings. Managerial triage and delegation are commonplace that makes handling asks from all sides especially important.

However, none of this was apparent to me in my first engineering management role. Even when I caught up with reality, I naively expected to handle the increased load without issue. I organized my to dos in a trusted app setup. I could juggle taking detailed notes while simultaneously participating in meetings with ease. But at some point, a few months in as my number of reports increased and work volume spiked my system started to break down. I was dropping follow-ups. I would bury away action items in notes I would forget to review later. It was at that point I realized I had to adjust my workflow. One of the biggest lifts came from adding ticklers to my routine.

I define a tickler as a reminder of anything that I need to review on a future date. For example, a Slack thread where I’m waiting for a response. Or a good idea that comes up in a meeting that I don’t have time to process now but potentially will later. I generally structure ticklers in the form of simple questions:

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Older films are getting harder to find

Popular streaming services like Netflix make it challenging to find films older than a few years. As these services increasingly dominate our movie watching time, fewer will be watching older movies. The net effect accelerates an already on the rise movie monoculture dominated by Disney, DC, and Fast and Furious. Fewer films that aren’t blockbuster franchises get made.

The problem starts with streaming service UI patterns, most of which have the same opening interface: a big highlighted promo area up top, followed by long rows of thumbnail content segmented into categories. As I wrote earlier, categorization in the rows can feel arbitrary. Navigating through a single row requires too much horizontal scrolling. In addition, the promo area dominates the visual hierarchy but rarely offers more than a single movie or TV series at a time.

So streaming UI makes browsing dicey for any film. Considering older films tend to be a fraction of the content on the opening page, they, in turn, become exponentially more difficult to find.

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Xbox’s marketing evolution

Opinions around Microsoft’s 90 minute Xbox & Bethesda E3 showcase are positive, a highlight alongside Nintendo’s outing in an otherwise quiet E3 year. But there have been pockets of criticism around the show’s lack of depth and “wow factor.” VG247 argued there were not enough “next-gen show stoppers”. Threads on Resetera, social media, and Digital Foundry knocked the Xbox presentation for having too many CGI trailers.

I’m sympathetic to missing more hands on time with Microsoft’s upcoming lineup. However, much of this “depth” criticism is myopic, relevant to an earlier era where Microsoft’s core focus was on the number of games and consoles sold. Thirty trailers in ninety minutes may not be an optimal pitch for $70 games and $500 consoles. However, it is a very sound approach to push Game Pass.

E3 2021 has made it abundantly clear that Microsoft has bet Xbox’s future on subscriptions. Keeping gamers hooked on Game Pass is a different, tricker pitch than buying high profile games. Variety is a must, with enough titles and genres to attract a wide variety of subscribers. Quantity can also help. Not every game will interest a potential subscriber, but the feeling that many more games are coming to the service over time adds to its sense of value.

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The wide range of next episode UI

How we get from one TV episode to the next on your streaming service of choice requires finesse. The right design pattern saves time through less menu navigation once you reach the end of an episode. But too aggressive of a yank to the next show generates a hurried feel, giving you barely a breath to process what you watched before zooming off to the next show.

The services I subscribe to today – Netflix, Amazon Prime, Disney Plus, Apple TV Plus – take different approaches to this next episode design challenge. All but Disney Plus have an algorithm that detects when you’ve finished an episode, generally the moment the closing credits begin to roll. At that point, UI appears to suggest moving on to the next show. This feature ensures I get the correct episode when I pick back up the series later.

Disney has no next episode detection and no corresponding UI at the episode’s natural endpoint. Continuing the “latest” episode of a show usually drops me midway through the previous episode’s credits. The net effect means I have to manually browse to get to the next episode.

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Xbox Game Pass respects my time

I’ve previously written Xbox Game Pass off as a poor fit for my busy schedule. I’m someone who rarely has more than an hour or two to play in one sitting and saw the service valuing quantity over quality. To my logic, instead of paying $15 a month for a lot of games I would never have time to play, I’d rather buy what interested me directly, without being restricted to the selection available on Game Pass.

But a few weeks ago, I pulled the trigger on an unexpected in stock Xbox Series X on impulse. A month later, having sampled many titles on Game Pass, it’s clear my initial hunch was wrong. Game Pass has ended up saving, not wasting, my time. I feel more engaged with my tastes and I have a better sense of where I’ll spend money on gaming a la carte in the future.

That’s because Game Pass games are effectively demos on steroids. There’s no barrier to entry; I can explore as much or as little of any game on the service. If a game isn’t working for me, I delete it and move on. Thanks to a fast fiber internet connection, the wait for that next game is rarely long; to date, I have multiple downloaded games “on deck” for this purpose. Over some time far shorter than it would take to complete your average AAA blockbuster I’ve trimmed my playlist to a handful of games that resonate with me.

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Navigating the downsides of remote first engineering management

Engineering teams working together in the same physical space every weekday will be a rarity. Fully remote and flex work was a phenomenon on the rise before 2020, and the pandemic exponentially accelerated these trends. Tech firms had to adopt a work from home culture overnight. After some initial growing pains, most companies found their productivity didn’t tank, and many of their engineers weren’t eager to head back to their open floor plan campuses. Today even companies with a strong office culture (Google, Microsoft, Salesforce) have shifted to a hybrid setup with the workweek split between the office and elsewhere. Other high profile tech companies (Square, Twitter, Shopify, Facebook) now allow employees to work fully remote.

There will be some holdouts like Apple that retain an in-office model. Still, momentum favors more distributed work setups over time. This new reality makes remote team management skills not just nice to have, but essential.

Having managed a team across the U.S. and Canada for several years, it can be challenging to keep meetings productive and helping the team gel together. If you’re read or listened to any other remote first advice, this isn’t revelatory news. But your actions in response to these headwinds can have a positive impact.

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The algorithms will not save you

The pandemic has upended movie watching. Our theaters are now our homes, with streaming services like Netflix and HBO Max our de facto movie watching hubs. Even long after COVID-19 is behind us, film distribution will not revert to the way it was in 2019. Brick and mortar theaters stay in shambles. Premium VOD will be untenable. Subscription services increasingly dominate.

Paradoxically, a movie watching landscape under the control of new technology can make finding content to match your tastes more difficult. Algorithms are not the answer. Instead, you’ll have to use some proactiveness and legwork to find your next great film.

That’s because almost every streaming service makes hunting for good content an ordeal. So much content can appear at once. Most services are intentionally obtuse with the details and it’s hard to know when a service adds or removes movies. Categorization can feel vague, misleading, and manipulative. A service will happily pay inflated prices for critically acclaimed festival winners and then proceed to bury them off the home page.

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PlayStation can’t stay the course forever

Xbox has been on a news tear lately. In early March, Xbox head Phil Spencer confirmed future Bethesda titles would only appear on platforms that offer Game Pass (read, not the PS5.) Days later, Square Enix revealed that the high profile action game Outriders would release on Game Pass in parallel with a full price retail rollout on other platforms. This one two punch crystalizes the biggest challenge to PlayStation’s market leader status. Sony has built a strong reputation on its platform exclusives, but the next Fallout or Elder Scrolls absent on PS5 will push many to Xbox this generation. Also, as Sony continues to press on with its $70 first party titles, Xbox Game Pass offering tentpole games at $15 a month looks increasingly tempting.

I hope this flood of recent Xbox news serves as a wake-up call to Sony. As Xbox differentiates itself from Game Pass, Nintendo on portability, and evergreen first party IP, Sony has some work to define its future direction.

In many ways that hook is a continuation of what Sony has done from the PS4 era: a curated collection of high caliber games that run exclusively, earlier, or best on PlayStation hardware. But that doesn’t mean a repeat of the same strategy from seven years ago. In 2013, well timed big budget exclusives could be the deciding factor, marketed through traditional channels on enthusiast websites, social media, and the occasional TV spot. Today we’re looking at an audience expecting more genre diversity, variety of price points, all while being fragmented across the internet.

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