The culture, the experiments, the engineering and the daily habits: what it takes to change a company that already works.
Starting a company with AI is one thing. Changing a business with existing staff, systems and customers is harder, and far more common.
We asked Jem co-founder and CEO Simon Ellis what he’d tell any founder trying to do the same.
Lessons from turning an existing SA company AI-native
1. Make it fun, not compulsory
Simon’s first AI memo in 2023 was ignored for 18 months, and mandates didn’t work either. What changed things was weekly Thursday hackathons with prizes, where people could build anything. Once colleagues saw each other building, scepticism turned into competition, and one customer-service agent ended up building AI agents.
2. Give every new idea a week, not 6 months
Jem runs 2 lanes: a growth lane for the core business and a discovery lane for new ideas. Each idea gets a week to prove itself before the team commits to building it. The aim is to get from idea to killed, or idea to moving forward, as fast as possible.
3. Expect your first experiments to fail
Jem switched off an AI voice agent after early errors, and Simon now calls that a massive mistake. Restarting took a couple of months. Judge experiments against the people doing the work today, decide in advance what success looks like, and narrow a struggling experiment instead of ending it.
4. Hand over routine work one step at a time
Jem’s engineering agent now resolves 92% of maintenance tickets on its own, freeing up 2 days a month for a 10-person team. It got there over about 18 months, starting with an expert reviewing everything and handing over more as trust grew.
5. Let AI tell you what to automate next
Every Sunday night, an AI task reviews Simon’s Slack, CRM and email, finds his 5 most repetitive tasks of the week, and suggests a skill or agent for each. It turns automation into a weekly habit instead of a guess.
The big payoff
None of these lessons needs a new company or a big budget. They need a culture that rewards trying, tolerates early failure, and steadily hands off work as trust builds. That’s how a 6-year-old company ended up with a team that has, in Simon’s words, overtaken him.
Want the full story?
Simon’s full panel from The Open Letter Cape Town 2026 is available to members inside the Founder Collab, where he goes further than we could cover here:
How to share context across offices in 3 cities
How Jem helps customers like McDonald’s adopt AI without fear
Why he wants 1,000 AI-native people, not 10
Why he now feels personally behind his own team
You’ll also get access to 40+ masterclasses from SA founders and operators on sales, fundraising, UX, paid media and more inside The Founder Collab.
Get more SA tech and business news, tips and business-building workflows and subscribe to The Open Letter.



