Overheard October: AI Founders on Work, Management and Culture

What founders are saying about the way AI is changing work inside their companies.

Image Source: Getty Images credit Bloomberg

Much of the narrative around AI and work is still about what might happen next. So what does work look like inside companies building and adopting AI right now?

This month’s Overheard conversations include a defence of generalists and a warning about teaching AI your old hiring habits.


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Daniel Chait, Greenhouse

"Hiring still runs on artifacts from the paper era."

Candidates are using AI to send more applications, and employers are using AI to filter them out. Chait calls it a hiring “doom loop”, which probably sounds familiar if you’ve looked for a job recently.


Barb Hyman, Sapia.ai

“If you train a model on historical hiring data … you’re not removing bias, you’re industrializing it.”

Hyman’s concern is that AI will learn to favour the same people employers have always favoured. If your hiring decisions need improving, teaching a machine to copy them is a questionable place to start.


Scott Downes, Supernal AI

“I think this is a great moment for the generalist.”

Some encouragement for those whose careers haven’t followed a straight line. Downes studied literature before moving into technology, and thinks people who can understand several parts of a business have plenty to offer as companies adopt AI.


Yasser Elsaid, Chatbase

“I think it’s a big mistake for founders to live in a future that doesn’t exist yet.”

Elsaid had thought AI would let Chatbase keep its team small. He’s since changed his mind: the company now has 40 employees and plans to double that within six months, because the models still need people to decide what to build and make sure it works.


Alan Chang, Fuse Energy

“A founder who doesn’t interview every engineer has already given up on quality.”

Chang still interviews every engineering candidate himself and makes an offer on the spot if they pass. Some of the founders and engineering leaders replying to his post wondered whether trusting his team to hire might be a better use of his time.


Ayush Sharma, Warp

“Most customers start by approving everything and expand autonomy as they gain confidence in the agent’s work.”

Warp’s agents handle payroll and HR tasks, with companies deciding how much freedom to give them. Even when you’re hiring software, it seems there’s still a probation period.


Tobi Lutke, Shopify

“I figured out who my most stressful meetings are with.”

Lütke’s personal AI agent combines his Fitbit readings with his calendar, giving him a rather specific answer to what’s raising his heart rate. He told the colleagues involved; apparently, they didn’t find it nearly as funny as he did.



Superhumxn Editorial Team

The Superhumxn Editorial team covers AI, leadership, organisational strategy, workplace culture and the future of work.

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