# SG - Chief of Staff, AI & Leadership Programs (4-month Contract) > Thinking Machines Data Science Inc. · Singapore, Singapore (Hybrid) · Contract · Posted 2026-09-09 **Salary:** SGD 3,000–4,000 **Workplace:** hybrid ## Description _**This role is under Immediate Hiring.**_ _**Due to work visa sponsorship limitations, we are only able to consider Singaporean Nationals or Permanent Residents for this role.**_ [Inherent](https://www.inherentjourney.com/) and Thinking Machines are jointly building a new kind of leadership program at the intersection of AI, decision-making, and organizational transformation. Our purpose is to create a human-centric AI learning where AI is used in ways that grow human thinking, relationships and values – while driving organizational outcomes. The program combines AI tools (personal second brains, AI-augmented workflows), leadership development frameworks, and real organizational use cases. More about the program and founders can be found [here](https://thinkingmachin.es/second-brains-executive-teams/).   We have strong customer demand across public, private and non-profit sectors. We are hiring a capable **Chief of Staff to organize, shape and scale this program with Stephanie Sy (CEO, Thinking Machines) and Karen Tay (CEO, Inherent)**. You will own the architecture — of the curriculum, the operations, the delivery model, and support the founders in client-facing delivery and business development.  Many of the concepts and tools we teach are at the cutting-edge. We will teach you – there is no need to be an expert on day 1. However, we need a strong learner who is highly organized and driven, works well in ambiguity and is aligned with our purpose to create human-centric AI learning experiences.  ### What You Will Do **1\. Curriculum & Program Operations** - Turn evolving content into clean, version-controlled curriculum — slides, exercises, pre-work, facilitator notes - Build and maintain session runbooks: timing, transitions, contingencies - Build and maintain train-the-trainer materials  - Ensure materials are structured so others can pick them up and deliver without briefing from the founders **2\. Workshop Delivery Support for Clients**  - Coordinate program logistics: participant comms, group setup, materials distribution - Support live sessions — timekeeping, troubleshooting, participant flow - Capture insights and patterns from each cohort to inform program refinement - Own the post-workshop follow-up process: surveys, next-step routing, relationship tracking - Own Whatsapp group for cohorts - designing and implementing human-in-the-loop agentic system for responding (We will teach you how)  - Own the feedback loop — capture what works, what doesn't, and make sure each session improves **3\. AI Tools & Program Testing** - You will be an active user of the tools we teach (ChatGPT Plus, Claude Pro) – you don’t need to be able to code. We will teach you to build your own second brain using the curriculum we deliver - Test new workflows, prompts, and setups before they go into the program — flag what works, what breaks, what confuses a first-time user - Help participants troubleshoot during and after sessions — you do not need to be a developer, but you need to know the tools well enough to unstick someone - Identify opportunities to use AI to improve our own operations: follow-up drafting, materials synthesis, participant tracking, session prep - Be the person on the team who is genuinely curious about what the tools can do — and who brings that curiosity into how we design the program **4\. Business Development**   - Articulate the B2C and B2B offerings clearly — what we sell, to whom, at what price, in what format - Build the pipeline operational infrastructure: lead tracking, follow-up cadence, opportunity routing - Create customer client-facing decks from our template materials - Work with our bigger team in the Philippines to refine our website and materials  **5\. Knowledge Management and Leadership Alignment**  - Keep track of all action items, agreements, documents so nothing falls through the cracks between two busy CEOs _This role is offered as a 4-month contract initially, with potential to extend based on business needs._ ## Requirements **Who This Is For** You have at least two years in consulting, the early stages of a startup, or an operational role (we welcome applicants with more work experience who want to immerse in AI and leadership development).  You find yourself naturally gravitating towards making sense and systems from ambiguous situations. You likely want to start your own startup/company some day.  You are: - Highly organized, but not just an administrator — you understand why the structure matters, not just what it looks like - A genuine AI user— you are already experimenting with AI tools in your own work, and you find the second brain concept immediately compelling, not abstract - Comfortable holding complexity: multiple workstreams, two principals, ambiguous scope - Proactive — you identify what needs to happen next without being told - Strong communicator — you can synthesize a messy conversation into a clear decision log - Comfortable working with senior stakeholders, and confident enough to push back when needed Bonus if you have: - Experience in program ops, management consulting, product management, or early-stage startups - Supported or run workshops, cohort programs, or training initiatives **What This Role Is Not** - Not a pure logistics or admin role - Not a passive coordinator who waits for instructions - Not a repetitive, process-following job You will be building something new — and doing it with two principals who both move fast and think big. The value you bring is structure, follow-through, and the ability to translate messy ideas into things that actually happen. ## Benefits **What You Will Get** - An opportunity to learn and practice working with cutting-edge AI tools  - Direct exposure to senior leaders and real organizational transformation work - A front-row seat to how AI tools are being applied and productized in leadership contexts - Start-up experience – the opportunity to shape a program from the ground up - Close collaboration with two founders who value initiative and will invest in your learning and growth ## Apply [Apply at Thinking Machines Data Science Inc.](https://apply.workable.com/thinking-machines-data-science-inc/j/99359C6CE4/apply) --- Powered by [Workable](https://www.workable.com)