How I Took on the Most Challenging Role of My Life and… | Proposify

How I Took on the Most Challenging Role of My Life and Saved Proposify

Being the Chief GIF Officer is a thankless job, but someone had to do it.

8 mins. read

It may come as a shock to some people, especially to those that work alongside me at Proposify, but when I first joined the company just two years ago I was brought on to be a full stack developer.

Yet when I started, I was immediately struck by one obvious truth: Proposify’s GIF game was weak. It was an absolute disaster.

There were myriad issues: low frame rates, washed-out or over-dithered colour palettes, and even the odd cinemagraph that would be trotted out as if it were actually a fully-fledged GIF.

I challenged Proposify’s co-founders, Kevin, Kyle, and our CTO, Jonathan, with this question: how can we possibly compete on a global scale when we were clearly using one-horse-town GIFs?

I knew then and there that Proposify needed me for more than just development. I needed to bring forth a new standard - nay, a new era - of giffery.

Now, you don’t need an MGP (Master of GIF Posting) to be a successful CGO. Even someone completely self-taught can turn a struggling company around with the right attitude. All it really takes is recognizing that there is a problem and caring enough to fix it.

How to identify a failing business

Bad GIFs.

Maybe their GIFs were just a paragraph of text superimposed over someone who wasn’t even talking.

A lot of the time, a GIF like this requires some knowledge of the context of the GIF to understand what makes it relevant. A GIF that gets posted in response to something should always have its relevance and be self-evident.

Maybe their GIFs had low frame rates.

A good GIF should always be smooth and pleasing to the eye.
Or maybe it should have just remained a jpeg.

Sometimes, the GIF medium can actually detract from a perfectly good image. Just because it CAN be a GIF doesn’t mean it SHOULD be.

Maybe their GIFs had a person mouthing a single word of the caption. When everything comes together to make a terrible GIF, you get something like this:

(note here how Kanye is clearly saying “Armpit”).

If you’re not going to include the person mouthing the whole caption, then it either shouldn’t be a GIF or it shouldn’t have a caption.

And so, in the summer of 2014, I assumed the thankless role of Chief GIF Officer. I was able to identify what needed to be fixed and acted upon those needs with ruthless efficiency.

Now, after two arduous years of helping the company grow, when I walk into the office each morning I can tell that I’ve earned the respect and adoration of my colleagues.  

At last I can say we’re competitive.

What makes a good GIF?

First of all, it’s a hard G as in ‘graphics’, you filthy animals.

Second, some basic and easy-to-follow ground rules:

  1. The frame rate of a GIF should be no less than twelve frames per second - precisely half of a standard National Television System Committee (NTSC) television broadcast. This guarantees every GIF is suitably smooth.

  2. The GIF should not loop backwards when it’s done playing (i.e. play forwards, then backwards) - that’s what we call the Devil’s Loop.

  1. The GIF should be emotive or otherwise pertain to the situation at hand.

  2. If a GIF war should emerge between two parties, no third party is to interfere - let the war run its course.

  3. One should always seek the highest quality GIF. Try to avoid GIFs with excessive brightness, contrast, or dithering.

  4. GIFs are for watching, not for reading! Don’t overuse GIFs as a replacement for the written word.

  5. If you’re the CGO at your company, whenever a GIF is posted it is the duty of the CGO to respond in kind with a better GIF.

When I started at this company we had less than twenty customers and each new acquisition was a major event.

We automatically emailed the team every time a new customer converted, and every time that happened we rang a bell. But we didn’t have a real bell yet (you can listen to this podcast about how we finally got one) so we had to ring virtual bells.

Here’s an example of a great GIF for ringing a bell.

And here’s a terrible GIF. Can you spot the problems?

Where’s the joy in this GIF?

It’s supposed to represent a joyous occasion, and yet every time I look at it I’m just depressed. One could make the defense that, based on the context of the GIF, it is funny in an absurd, ironic way (the above GIF is from a particularly tense scene in Breaking Bad).

And yet as I’ve stated before, a GIF should be good without a tongue-in-cheek reference to its context. Initially, my words fell on deaf ears and I had to constantly combat bad bell gifs, dealing with resistance from my colleagues time and time again.

It’s important to always be firm when people need to learn how to be world-class:

But sometimes, like the time our CTO, Jonathan, learned he could just link to GIFs instead of downloading and then uploading them to Slack, the results could be worth it:

What makes a good CGO?

Being a CGO isn’t always filled with the awe of your peers. Sometimes, a good CGO needs to know when to truly put their foot down.

As Michael DeLuise did to Sean Astin in the great masterpiece of the 90’s, Encino Man, sometimes you just have to shut them down.

Here’s an example of when I had to put my foot down and lay down the law:

Just a year ago, Kyle ceremoniously enabled a Giphy integration for Slack.

It was hailed as the dawn of a new era in giffing, one in which the exchange of GIFs could be performed freely without the watchful eye of Proposify’s own CGO.

How did this integration work?

It was as simple as typing “/giphy” and then a keyword. For instance, “/giphy memory” would do a search for gifs that were tagged with the word “memory”.

The company was still small at the time (just five employees total) and I was able to keep the lid shut on the Giphy integration. Managing the GIF trade was easy when there were so few people, but now that we’ve become a company of 12, regulation has become ever more necessary.

And yet, in a moment of weakness that to this day still haunts me, the lid came off and the Giphy integration was unleashed upon the masses, leading to some horrifying misuses of the medium.

For instance, there was the time Geoff, the youngest member of our team, wanted to call us his friends and in his youthful naiveté decided to use the completely uncurated powers of Giphy:

Or maybe the GIFs just made no sense whatsoever and the conversation took a downward spiral into a meta-discussion on what the GIF meant.

In some instances, team members would intentionally abuse the system to just see what sorts of things Giphy would find. It was up to me to show them the error of their ways.

Altogether, the sudden influx of GIFs made actual, meaningful discussion in Slack grind to a halt. It was after almost two full days of this madness being unleashed upon our Slack channel and my continued efforts for Giphy teetotalism that people began to understand why the position of CGO is so necessary.

After an impassioned defense of continued regulation in the GIF economy, at last the Giphy integration was disabled and sanity once more returned to Proposify’s Slack channel.

Order was not the only thing to come to Slack, but I dare say, a whole new appreciation for the art of GIFs.

Out of the ashes of the corpse of Giphy rose as a phoenix a GIF renaissance. With chaos firmly behind us, Proposify employees finally understood what made for a good gif, and were able to even hold a conversation with GIFs as the primary means of communication.

The importance of keeping things fun

Now that you know what it takes to be a good CGO and you’ve established a baseline of quality in your organization, it’s time to relax.

As a wise princess once said, “The more you tighten your grip, the more star systems will slip through your fingers,” and this is true a thousand-fold for GIFs.

You’ve already done all of the legwork - now is the time to just sit back and watch your colleagues express themselves like never before.

In a developing organization, there’s often a marked shift in the requirements of the CGO. You stop being the enforcer and transform into the chaperone.

It’s like a middle school dance - the children can mostly take care of themselves so your job is to make sure things don’t get too unruly.

Or, perhaps, the kids won’t mingle and the dance gets a little stale. Then it’s your job, like any good chaperone, to mix things up and bring GIFs to the forefront.

Sometimes all it takes is saying, “It’s time for Chris Farley GIFs.”

So your GIFs are strong and your company is a success - now what?


Bad GIFs are a distraction and nuisance at best and, at worst, actively hinder productivity by increasing the noise in chat channels that could otherwise be used for discussion.

What is your company doing to combat the tyranny of the bad GIF? Have you brought a CGO aboard yet?

What’s your favourite GIF?

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