I'd like to take this opportunity to thank Yaakov for all that he's done in his role as a developer and as Community Advocate, and to talk a little bit about Yaakov's history with the community and with me in particular.
My first interaction with Yaakov was in July 2019. I had just written up a post, entitled "Let's take a look at the interaction between staff and the "power users" of the network", detailing a large number of frustrations and issues that the power users of the network - such as the moderators - had been having with the company.
It had been a tough little while for the network, as the post makes clear - from unpopular redesigns to neglected tooling, relations were strained.
Yaakov posted an honest, thoughtful answer, acknowledging that there were legitimate reasons for frustration and giving an honest, clear view on how the company had been and would be operating. That was the start of what would become a long history of Yaakov carefully navigating thorny community-company interactions, despite being a developer and not officially on the Community Team.
A few months later, things reached a boiling point. The network underwent an unprecedented period of tension, arguments, drama, and everything else - you name it. (Trying to read the Teachers' Lounge transcript after 25 hours offline meant catching up on over ten thousand messages... and that was just one room.) Dozens of moderators resigned.
Two open letters were composed: A mod open letter, and the lavender letter.
While everything was still in an uproar, Shog9 and Robert Cartaino were let go - both long-time Community Managers and very well-respected by the community. A short while after that, Jon Ericson (another CM) also left. This left Stack without many of the people that regularly communicated with the community.
With that loss, Yaakov stepped up to fill some of that void. A new CPO (Chief Product Officer), Teresa Dietrich, had just arrived on the scene. Yaakov worked closely with Teresa to make sure she was aware of and understood the situation.
At that time, I was also working directly with Yaakov in two different ways.
The first way was to help in resolving the issues raised in the Lavender Letter. I, along with two other moderators at the time, had a video meeting with Yaakov, Teresa, and Adam Lear, and then joined a Slack channel in Stack Overflow's internal Stack to further work on resolving those issues (with a focus on moderator spaces).
At the same time, after Shog and Robert had been let go, people had been working on coordinating action for a strike. I worked together with Yaakov to pass on updates on the strike coordination and how things were progressing to Stack internally; Yaakov was able to use this as leverage inside the company to prioritize these issues and get leadership to fast-track resolving things - particularly, publicly responding to the Open Letter - before the strike actually went into effect.
This was successful; Teresa posted The company’s commitment to rebuilding the relationship with you, our community a day or so before the strike was slated to begin. It was a sincere effort to turn things around, and for a while, things did improve, and the rebuilding process was underway.
As time went on, Yaakov became a familiar face around meta, from his poetic answers to the Defender of the Unicorn, to work on the Staging Ground, and more.
Yaakov also officially took on the additional role of "Community Advocate" - while not on the public-facing Community Team, he would advocate for and raise awareness about the community inside the company, such as educating people on the history of the community and more.
In mid-2021, I actually met up with Yaakov in person, where he treated me (and Shadow) to a drink at a restaurant. We chatted for a while, talking shop (Stack) and life, and we've since kept a little WhatsApp group named cheekily after the Tavern.
Unfortunately, relatively recently, tensions once again flared between the community and the company. Once again, the idea of a strike was floated; this time, the idea of a strike caught on much faster than in 2019, and as the company's position remained unchanged the pieces began to quickly fall into place.
Once again, before the strike started, Yaakov tried to facilitate communication. In the Discord server where strike coordination was happening, Yaakov read through the demands that were being drafted and opened discussions about how Stack could meet them. He took feedback directly to the company and to Philippe (Vice President of Community) from the community, and vice versa, giving those of us in the Discord server heads up about stuff from the company and making communication faster.
Unlike in 2019, though, the company didn't change course, and the strike went into effect. Yaakov's efforts didn't stop, though; he reached out to facilitate the strike coordinators choosing negotiation representatives, and helped set up a neutral negotiating space where conversation could happen between the company and strike representatives. I worked personally with Yaakov on making sure that the space wasn't directly controlled by either party, and to ensure that the ground rules allowed for working with the broader community to discuss any potential resolutions.
During the course of the negotiations, there were a few hiccups, but Yaakov helped to communicate and adjust expectations around what was going on. In the end, despite those hiccups along the way, the negotiations were a success. An agreement was reached, it was announced to the public, and the community voted to end the strike.
The successful resolution was due in no small part to Yaakov's efforts to facilitate and improve communication, often keeping the same insane sleeping hours that I was while everything was going on.
Yaakov's near-constant efforts to communicate and break down barriers have earned him a well-deserved reputation among the community. I'm confident that I speak for almost everyone when I say that he'll be deeply missed on many levels; for his efforts in community-facing work and communication, and also for the deep knowledge and understanding of the Stack Exchange systems. Having been a developer on the site for over ten years, it's hard to think of many others who would have as much of an understanding of the inner workings of the site as Yaakov. That loss of institutional knowledge is a blow on both the technical and community sides.
But after ten years, anyone could use a change of pace. Yaakov, your new company has gotten hold of a rare gem; hopefully they'll recognize that. Enjoy the challenge of a new working environment, and all that it entails; in the meantime, חנוכה שמח and stay safe. We'll miss you here.