The 90-Day Singapore
CEO AI Playbook
What every Singapore CEO should do between 6 May and 28 July 2026 — based on what the government has already signalled.
"The PM gave the signal. This is the response."
Five concrete actions across 12 weeks. Every action has a deadline, an owner, and a measurable output. Built for CEOs who want to act on Singapore's 400% AI tax deduction window before the rest of the country catches up.
Compiled by Prabjeet Singh Anand. CEO, PeopleCentral. Founder, AI CEO Brief. 20 years building businesses in Singapore. Source-checked against PM Wong's May Day 2026 address and Singapore Budget 2026.
Why This Playbook Exists
On 1 May 2026, Prime Minister Lawrence Wong told the country what is coming.
"Jobs will change. Some will disappear. The pace of change will be faster than anything we have seen before."
He also committed government resources to support workers through that change — the 400% AI tax deduction, the Champions of AI programme, the National AI Council.
Most CEOs heard the speech. Few have a plan.
This playbook gives you a 12-week plan that aligns with what the government has signalled. By 28 July 2026, you will have:
- Briefed your CFO and board
- Audited and categorised your AI spend
- Identified the right starting workflow
- Run a 14-day intelligent layer test
- Communicated the change to your team
Reading this after 6 May 2026?
Sequential — start from Week 1 today and run it forward 12 weeks. The dates in the playbook become guidelines. The sequence is what matters.
Aligned to the deduction window — the Singapore EIS AI deduction runs YA 2027 (FY2026) and YA 2028 (FY2027). Every quarter you run this playbook before 31 December 2027 captures qualifying spend. There is no penalty for running it later. There is a penalty for not running it at all.
The Sequence at a Glance
CFO briefed. Board aligned. AI spend audited. Framework documented.
Workflow chosen. Vendor shortlisted. PSG checked.
14-day test run. Results measured. Team briefed. Documentation filed.
Month 1 — May 2026 — The Foundation
The first 30 days are about getting the people and the documentation right. No technology decisions yet.
Week 1 — Brief your CFO
Send your CFO the Singapore AI Tax Deduction CEO Guide. Schedule a 30-minute call with them this week. The conversation: "The PM confirmed last week what was already in Budget 2026. There is a S$50,000 cap on qualifying AI spend that gets a 400% deduction. That is S$34,000 of tax saving available to us this year. Can you confirm by Friday that we have the right expense category in place?"
- CFO has confirmed your company structure qualifies
- CFO has agreed to set up a separate expense category: Qualifying EIS AI Expenditure — YA 2027
Week 2 — Audit current AI spend
List every AI-related expense in your business year-to-date. Categorise as qualifies / probably qualifies / does not qualify.
- Spreadsheet of every AI-related vendor and subscription
- Estimated qualifying spend already incurred in 2026
- Identification of any spend at risk of being misclassified
Week 3 — Brief the board
Add AI to the next board agenda. Use the CFO briefing pack as the supporting document. Bring one slide: the 400% deduction window, S$34,000 tax saving at 17% CIT, closing 31 December 2027. Recommend approving up to S$50,000 of qualifying AI investment this financial year.
- Board has been briefed on the 400% deduction window
- Board has approved an AI spend envelope for FY2026
- Board minutes record the decision (this matters for IRAS audit)
Week 4 — Document the framework
Draft the internal AI investment framework document for your business. One page. Lock the principles: add intelligent layers not replace systems; every AI vendor invoice must explicitly describe the AI capability; run 14-day tests not six-month pilots; communicate AI changes before the change happens.
- One-page internal AI investment policy
- Qualifying spend criteria documented for procurement
- Vendor invoice template requirement specified
Month 2 — June 2026 — The Selection
By 30 June, you should know exactly which workflow you are starting with and what tool you are using.
Week 5 — Find the bottleneck wearing a job title
Send this message to every team lead: "I am looking at where AI could give our team time back. Can you tell me the one task you do every single week that takes the most time and produces the least judgment? Not the most important task. The most repetitive one. Reply by Friday."
- 5 to 10 candidate workflows from team leads
- Each workflow named with hours per week and number of people involved
- Initial ranking by total annual hours recoverable
Week 6 — Calculate the time-back number
For your top two candidate workflows, calculate recoverable hours: Hours per week × number of people × 50 weeks = annual hours recoverable. Example — 4 hours/week × 3 staff × 50 weeks = 600 hours/year.
- Two ranked candidates with total annual hours recoverable
- Estimated value of those hours at fully-loaded staff cost
- Decision: which one to start with
Week 7 — Shortlist vendors
Identify three vendors that could provide an intelligent layer for your chosen workflow. Filter: Singapore presence or strong APAC support, pricing within S$50,000 qualifying envelope, ability to sign an SOW that explicitly maps spend to AI deliverables.
- Three vendor shortlist with documented AI capability
- Pricing for each vendor
- Confirmation that each vendor will issue itemised invoices describing AI components
Week 8 — Check PSG eligibility
For your chosen vendor, check whether the tool is PSG-supported through the Business Grants Portal. Two paths: PSG eligible — apply before purchase, claim EIS 400% on out-of-pocket portion only. PSG not eligible — claim EIS 400% on the full qualifying amount.
- Confirmed whether PSG applies
- Documented split if PSG applies (PSG portion vs out-of-pocket)
- Decision: stack PSG + EIS, or claim EIS only
Month 3 — July 2026 — The Execution
By 28 July, you should have run a 14-day test, measured the result, and made a scaling decision.
Week 9 — Run the 14-day test
Deploy the chosen tool to a small group (3 to 5 people) for 14 days. Measure baseline hours before AI, performance during the two weeks, and error rate vs manual baseline.
- Baseline measurement: hours spent on the workflow before AI
- Two-week performance log: hours spent on the workflow with AI
- Error rate: AI output errors vs manual baseline errors
Week 10 — Measure and decide
Review the test results with your team lead and CFO. Decision rule: recovered ≥60% of calculated time AND error rate ≤ manual baseline → SCALE. Recovered <60% OR error rate > manual baseline → STOP, review, try different layer.
- Documented results report
- Scale decision (yes or no) with reasoning
- If yes: rollout plan for the next 90 days
- If no: alternative vendor or alternative workflow identified
Week 11 — Communicate to the team
Brief the affected team on what happened, what changed, and what comes next. Cover: what we changed, why we changed it, what it means for your role specifically, what we will not change, and what you should do this week.
- All-hands or team meeting where the change is announced
- Written FAQ document for affected staff
- Confirmation of any role changes or new responsibilities
Week 12 — Document for IRAS
Build the supporting documentation folder for the AI investment. This is the folder you produce at IRAS audit. Build it now while every detail is fresh.
- Vendor invoice with AI capability described
- Vendor SOW or contract specifying AI deliverables
- Implementation plan
- PSG approval letter if applicable
- Internal use case document
- Adoption metrics from the 14-day test
What comes next — August 2026 onwards
By 28 July 2026 you will have completed your first intelligent layer deployment. The playbook ends here, but the work compounds from this point.
You already have the framework, the vendor criteria, the test methodology, and the documentation pattern. The next 90 days will move twice as fast.
Enough qualifying spend documented to maximise the FY2026 deduction.
The second year of the deduction window captured before it closes.
The intelligent layer compounds. Each workflow you complete makes the next one cheaper, faster, and lower-risk to deploy.
What You Will Have at the End of 90 Days
What This Playbook Is Not
This is not a substitute for tax advice. Always verify with your IRAS-accredited tax adviser before claiming.
This is not a guarantee of results. AI layers fail when data is messy, workflows are too unique, or teams are not brought along. The playbook reduces those risks but does not eliminate them.
What this playbook does is give you a defensible, repeatable, government-aligned plan for the next 90 days.
Primary References
- PM Lawrence Wong's May Day 2026 address — bloomberg.com
- Singapore Budget 2026 — Ministry of Finance — mof.gov.sg/singaporebudget
- Enterprise Innovation Scheme — IRAS guidance — iras.gov.sg
- Productivity Solutions Grant — businessgrants.gov.sg
- Champions of AI Programme — EnterpriseSG — enterprisesg.gov.sg
Verify all current scheme details directly with IRAS or your tax adviser before claiming.
Three Ways to Take This Further
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Ready to run the first 30 days?
Start with Week 1. Brief your CFO this week. The S$34,000 tax saving window closes 31 December 2027. The earlier you start, the more of it you capture.
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Prabjeet Singh Anand
CEO, PeopleCentral · Founder, AI CEO Brief · Singapore
20 years building technology companies in Singapore. His ecosystem of AI-powered products — PeopleCentral, HireCentral, TimeCentral, EngageCentral, and ReimburseMe.ai — serves 1,000+ businesses and 100,000+ users across Southeast Asia. Named Singapore Entrepreneur 100 in 2024.
This playbook is for informational purposes only. It does not constitute tax, legal, or financial advice. EIS qualifying AI expenditure details are subject to IRAS guidance. Always verify with qualified advisers before making claims. Last updated: May 2026.