The 90-Day Singapore CEO AI Playbook

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, and communicated the change to your team.

Reading this after 6 May 2026? Use the sequence as a guide. 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

Month 1 — The Foundation

The first 30 days are about getting the people and the documentation right. No technology decisions yet.

Week 1 — Brief your CFO

The single action: Send your CFO the Singapore AI Tax Deduction CFO Briefing Pack. Schedule a 30-minute call with them this week.

Specific outputs:

• CFO has read the briefing pack
• CFO has confirmed your company structure qualifies
• CFO has agreed to set up a separate expense category: Qualifying EIS AI Expenditure — YA 2027

"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. I want to make sure we are set up to capture it. Can you confirm by Friday that we have the right expense category in place and a documentation process for AI vendor invoices?"

Week 2 — Audit current AI spend

The single action: List every AI-related expense in your business year-to-date. Categorise as qualifies / probably qualifies / does not qualify.

Questions to answer:

• Which subscriptions are pure AI tools versus generic SaaS with AI features?
• Which consulting fees were specifically for AI implementation?
• Which staff training was AI literacy under a SkillsFuture-approved provider?

Most Singapore SMEs have already spent S$15,000 to S$30,000 on AI without knowing it qualifies. Capture what you have already done before you plan what comes next.

Week 3 — Brief the board

The single action: Add AI to the next board agenda. Use the CFO briefing pack as the supporting document.

Specific outputs:

• Board has been briefed on the 400% deduction window
• Board has approved an AI spend envelope for FY2026 within the qualifying limits
• Board minutes record the decision (this matters for IRAS audit)

Singapore Budget 2026 — Enterprise Innovation Scheme AI deduction. 400% on qualifying spend up to S$50,000 per year. S$34,000 tax saving at 17% CIT. Window: YA 2027 and YA 2028 only. Closes 31 December 2027. No carry-forward. Recommendation: approve up to S$50,000 of qualifying AI investment this financial year.

Week 4 — Document the framework

The single action: Draft the internal AI investment framework document for your business. One page. Lock the principles.

The five principles to lock:

1. Add intelligent layers, do not replace systems
2. Every AI vendor invoice must explicitly describe the AI capability
3. Categorise spend in the dedicated EIS expense category from day one
4. Run 14-day tests, not six-month pilots
5. Communicate AI changes before the change happens

Month 2 — 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

The single action: Send this message to every team lead in your business by end of week:

"Quick request. 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."

You will get more clarity from those replies than from any AI consultant deck. Apply the four-question filter: Does it happen at least weekly? Does it follow a repeatable pattern? Is the input mostly structured? Can a human verify the AI output in under 60 seconds?

Week 6 — Calculate the time-back number

The maths:

Hours per week × number of people × 50 weeks = annual hours recoverable

Example for invoice processing: 4 hours × 3 finance team members × 50 weeks = 600 hours per year recoverable. That is the number the AI layer must beat.

Week 7 — Shortlist vendors

Identify three vendors that could provide an intelligent layer for your chosen workflow. Filter for: Singapore presence or strong APAC support; pricing that fits within your S$50,000 qualifying envelope; ability to sign an SOW that explicitly maps spend to AI deliverables.

Week 8 — Check PSG eligibility

For your chosen vendor, check whether the tool is PSG-supported through the Business Grants Portal. If PSG eligible: apply for PSG before purchase. Claim EIS 400% on the out-of-pocket portion only. Document the split before you spend, not after.

Month 3 — 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 two things: hours recovered against baseline, and error rate against the manual baseline.

Decision rule at end of 14 days:

• Recovered ≥60% of calculated time AND error rate ≤ manual baseline → Scale
• Recovered <60% OR error rate > manual baseline → Stop, review, try different layer

Week 10 — Measure and decide

Review test results with your team lead and CFO. A clear decision rule prevents drift. Document the results and the decision with reasoning.

Week 11 — Communicate to the team

Brief the affected team on what happened, what changed, and what comes next. Use the five-part framework:

1. What we changed (the AI layer added)
2. Why we changed it (the time recovered)
3. What it means for your role (specifically)
4. What we will not change
5. What you should do this week

"We may not keep every task as it is today. But we will support every person through this change."

Week 12 — Document for IRAS

Build the supporting documentation folder for the AI investment: vendor invoice with AI capability described, vendor SOW, implementation plan, PSG approval letter if applicable, internal use case document, adoption metrics from the 14-day test. Build it now while every detail is fresh.

What Comes Next — August 2026 Onwards

By 28 July 2026 you will have completed your first intelligent layer deployment. Start the next workflow using the same sequence. The framework, vendor evaluation criteria, test methodology, and documentation pattern are already in place.

By 31 December 2026: three workflows running on intelligent layers. Enough qualifying spend to maximise the FY2026 deduction.

By 31 December 2027: five workflows running. The second year of the deduction window captured before it closes.