CEO Office

PH - Chief of Staff, CEO Office

Preferable Location(s): Taguig, Philippines
Work Type: Full Time

Working at Thinking Machines

Thinking Machines is a technology consultancy building AI & data platforms to solve high-impact problems for our clients. Our vision is a future where data-driven decision-making is a norm and where AI is used to support humans in making excellent decisions. To do that, we create data cultures, one organization at a time.

We’re a company composed of intellectually curious, civic-minded, forever-learning individuals. We believe great data science products are built with care for people and the best way to drive inclusive innovation is to start with a diverse team.

Our field of work is incredibly dynamic, so we want to work with people who are committed to growing with us. We want to hire people who can demonstrate an ability to learn, then provide them with personalized coaching, growth opportunities, and a great working environment to get them to world-class. 


The Chief of Staff (CoS) will serve as an aide to the CEO, playing a critical role in the orchestration of strategic initiatives in the company. This position asks for a high degree of organizational prowess, adaptability, and an exceptional ability to manage stakeholder relationships ranging from internal leadership, C-level clients, board members, and Thinking Machines staffers. The job will be to support the CEO in business expansion, operations management, and developing technology strategy playbooks for new AI and data tech. Excellent critical reasoning and writing skills are a must, as well as project management capabilities and an understanding of how technology products are built.

This role, expected to last two years, leads to advancement into a senior position aligned with the CoS's strengths, interests, and talents. The previous Chief of Staff was promoted to Product Manager of GenAI Solutions at Thinking Machines after her stint.

Thinking Machines is a leading Southeast Asian data technology consultancy. With 200 colleagues across offices in Manila, Bangkok, and Singapore, TM builds AI and data products for better organizational decision-making. See examples of our work. We strive to be the region's leading talent hub for data professionals and the top consultancy for data transformation.

Our CEO Stephanie Sy started her career as a data scientist in the San Francisco Bay Area tech scene before starting TM. Recognized internationally, she is an awarded leader and speaker. You can get a feel of her management style and personality in this podcast.

Key Responsibilities

  • Serve as the CEO's primary aide, ensuring flawless execution and communication of strategic initiatives

    • Strategic project manager. Facilitate meetings, providing stellar note-taking and synthesis to capture insights and actions utilizing GenAI tools where appropriate. Owner of project boards, email correspondence, and presentation decks.
    • Support high-level decision-making processes and act as a liaison between the executive and the rest of the organization. As the vital link, attend meetings on behalf of the CEO and arm decision-makers with context / critical information on the CEO’s behalf.
  • Support the CEO in managing relationships with key stakeholder clients and investors.
    • Manage and optimize the CEO’s calendar, including scheduling across multiple time zones, ensuring efficient allocation of the CEO’s time.
    • Ensuring that meetings are correctly synthesized, and actions are assigned to the right parties for follow-through
    • Directly working under the CEO’s direction on major business development opportunities such as commercial partnerships and joint product development
  • Embody the company’s core values of Growth Mindset; Relationships Matter; Trust and Accountability; and Build for the Future. Culture carrier who believes in fostering a culture of inclusivity and excellence.

Required Qualifications

  • A minimum of three years in relevant roles, with a preference for candidates possessing over five years of experience. Relevant fields include tech startups, technology consulting, or digital transformation
  • Track record of success in project managing complex initiatives
  • Excellent writing and communication skills using both memo and deck formats.
  • Intermediate Excel/Sheets modeling skills - able to independently handle using mixed formulas and managing workbooks with multiple referenced sheets
  • Calm, poised, and versatile in handling ambiguous situations. This is a time of industry-wide shifts in the AI space.

Nice to Have

A great chief of staff will bring their own unique experiences and skills to the role. Candidates who demonstrate excellence in any of the areas below will have a leg up:

  • Tech startups from either the operator or investor side
  • Writer and content creator
  • Coder and builder
  • Able to speak conversational Tagalog, Thai, or Bahasa


  • Role Location: Philippines
  • Role Setup: Hybrid Remote. Expect to be on-site with either clients in Metro Manila or at the Thinking Machines offices in BGC about 1-2 days per week.
  • Working Hours: Flexible hours, primarily 9:30 AM to 6:30 PM Mondays to Fridays. Working hours may vary due to the startup nature and international client collaboration.

What You’ll Get

  • Direct mentorship from the CEO. The senior leadership team of Thinking Machines has a track record of cultivating talent, helping them to discover their potential and challenging them to excellence.
  • An inside view of a high-growth startup in a high-growth industry - this is an ideal opportunity for someone considering starting their own startup or leaping up several levels of professional growth managing a technology company.
  • Cash and bonus compensation aligned with the top quartile of Philippine corporations and startups.
  • If you’re interested and motivated, but don’t feel like you meet every single qualification, we encourage you to give it a shot and share what you can contribute. The worst thing that could happen is that we say no.

Application Process

Interested candidates are requested to put together a cover letter indicating what unique experiences and skills they bring to the table, and what they hope to get out of the role. Please attach this letter along with your updated resume to the application form below. 

Candidates who make it through the first screening can expect the following process:

  • Past Portfolio Panel Interview. 75-minute walkthrough where you’ll be interviewed on your past experiences and you will be asked to present a work sample. Please pick 1 work sample that encompasses a quantitative analysis plus a presentation deck to present and answer questions about. If you do not have work samples available, let us know and we can discuss having you create a custom quantitative model and presentation instead.
  • Prompt Writing Live Exam. 45-minute live session where you’ll be asked to write and improve a GenAI prompt in response to a scenario. Previous experience in writing GenAI prompts is not required for the job, but you must be willing to learn. In this interview, you must be able to show critical reasoning skills.
  • Culture Fit Interview. 60-minute F2F interview with the CEO


We are running this application period between April 14 to May 14, and making offers in the second week of May. The selected candidate would start this job on June 15 or earlier.

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