For people who didn’t plan to be reskilling this year
Reskill with AI, on your own terms.
A small, calm playbook for Singapore-based business professionals — particularly millennials and Gen X — who got the memo about AI when the layoff email arrived. No hype, no hustle, no “you’ve got this”. Just a loop you can actually run this week.
We’ll help you map the skills that matter for your role, ship a portfolio, and quietly make yourself findable again. Two ways in: do it yourself with the free co-pilot, or join a small-group cohort run by On The Ground.
Why now, in Singapore
Singapore is a small, networked market. Hiring still happens through warm intros and quiet shortlists. When companies cite AI in a layoff, the question that matters isn’t how do I beat the algorithm — it’s how do I show up to the next coffee with a sharper version of what I already do?
The honest answer: spend a week using AI on the work you used to do. Map the leverage. Ship something small. Make yourself easy to find. That’s the whole loop. The rest is repetition.
The AI Reskilling Loop
Six steps. Run it once in a week. Run it again every quarter.
- Reset. Set up Claude (or your AI of choice) and treat it like a colleague. The point isn't to play with prompts — it's to give yourself one trusted thinking partner before anything else.
- Map. Describe a typical day in your old role to the AI. Your competencies. The metrics you were goaled on. Ask: which ten high-leverage AI skills would turn me into a 10x version of this role? Pick five. Iterate to a dozen.
- Build. Build a small portfolio site that shows the skills in action — not just the description. Walk through the business impact of each. Vercel is fine. So is GitHub Pages. The medium is the message: you can ship.
- Share. Link the portfolio everywhere — email signature, LinkedIn header, WhatsApp bio. Write a short note that starts with where you are and what you're open to. Quietly send it to ten people who would care.
- Learn. Take Anthropic's free Claude Code courses. Pick one community. Block four hours a week. Reskilling isn't a sprint — it's a loop you keep running on yourself.
- Be findable. Submit a Visible In SG profile. One URL, one QR code, one face. The point of the loop is to make yourself easy to discover for the people you'd actually want to work with.
Who this is for
Mid-career business operators in Singapore who want to use AI on their actual work. A few examples:
- Marketing leaders rebuilding a growth motion with AI in the loop.
- Operators between roles who want a sharper portfolio than “Open to work”.
- Finance and ops folks turning workflows into prompts and small agents.
- Founders between ventures looking for the next leverage layer.
- Anyone whose last layoff email used the words “AI-driven restructuring”.
Want a hand running the loop?
On The Ground runs small cohorts — usually six to twelve people — for Singapore-based professionals who’d rather not do this alone. Four to six weeks, live sessions, real critique on your prompts and your portfolio, and warm intros to hirers in the Visible In SG network when you’re ready.
Pricing depends on intensity (mastermind versus 1:1) and we’ll share it once we know the fit. The apply form is short. A real person replies within two business days.
Apply to the cohort
Tell us where you are. We’ll come back with whether the next cohort is the right fit, what it costs, and what to expect.
Common questions
- Do I need to know how to code?
- No. The loop is built for business professionals — marketing, ops, sales, finance, comms, product. If you can use Notion and Slack, you can do this.
- Will this work if I'm 45+?
- Yes. The strongest reskillers we've seen are mid-career operators who know what good work looks like. They have judgment to lend the AI; first-jobbers don't.
- How long does it take?
- The first pass — Claude set up, top skills mapped, portfolio shipped, profile live — is realistically a week of focused effort. Three to four hours a day, not eight.
- How is this different from a course?
- A course teaches you about AI. This teaches you to use AI on the work you already know how to do. The output is a portfolio you can send to a real recruiter, not a certificate.
- Is it free?
- The six-step loop on this page is free. The co-pilot tool is free with light limits. The On The Ground cohort is paid — start with the apply form and we'll send pricing once we know the fit.
- What does the cohort cover?
- Small-group sessions over four to six weeks: live work-throughs of the loop, prompt and skill review, portfolio critique, and warm intros to Singapore hirers in the Visible In SG network.
- My last role was non-technical. What's in it for me?
- Most of it. Non-technical operators have the most to gain because the leverage is in domain judgment plus AI execution. Marketing, finance, legal, ops — every one of these has an AI-augmented version that pays better.
- I was just laid off. Where do I start?
- Open the co-pilot. Spend twenty minutes describing your old role and your strengths. You'll come out with a shortlist of skills to practise this week. That's a real thing you can do today.
- Is my data safe?
- We don't store the inputs you give the co-pilot. The apply form is stored only as long as we need it to follow up — capped at 24 months — and is governed by our Privacy Policy.
- What if I just want the directory, not the programme?
- That's fine. Skip everything and submit your profile. The directory is free and always will be.
Make yourself findable while you reskill.
The loop only works when other people can reach you. Submit a Visible In SG profile — one URL, one QR code, one face. Quiet, human, free.