Originally published as an internal post at Automattic. Altered for a wider public.
What will jobs in support look like in six months from now? My hunch is that most people working in our industry have asked themselves this question several times in the past years. While the specifics are still in flux as AI is developing rapidly, I’m convinced that everyone in the support industry will need to develop leadership skills.
Why? Because we all will be leading a team.
Most of us are still using AI as a copilot. We prompt the tool, we review the output, and we use that output in assistance of our work. That’s changing. Agentic AI — where we direct AI to complete work autonomously — is already happening in parts of Happiness, Automattic’s support division, and it’s going to become the default for all of us. We will have multiple AI agents working for us.
We won’t be just using these agents, we’ll be leading them — and that is something I believe we already should know about where our jobs are changing.
An example. Recently, several support agents attempted to vibe code bug fixes for problems that had been open for months. Shortly into that test, my team focused on AI-powered support, built a Claude skill to do much of this work for our Happiness Engineers. Similarly, they have built a skill that automates the creating of documentation updates around product releases. If the agent produces poor work, I’m not going to ask the agent why, I’m going to chat to those team members. They’re its team leads. I’ve for example already asked them at one point they will trust it to publish directly without a human review. That’s the type of question a team lead would be asking while onboarding new team members because it evaluates the performance of that team member.
This isn’t unique to Happiness. Recently, our leader Matt shared how YCombinator CEO Garry Tan works with a set of AI agents he describes as his team, each with their own role, and each accountable to him. Tan decides who does what, and he owns the outcome. He leads the team.
The support people who thrive at Automattic in the next few years won’t be the ones who use AI best. They’ll be the ones who lead it best. What will it take for you as support staff to become that team lead?
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