Chief of Staff

About Iterative

Iterative is an accelerator that invests exclusively in startups in Southeast Asia. Founded in March 2020 by Hsu Ken Ooi and Brian Ma, Iterative has raised $65M across 2 funds, invested in 65+ companies, 120+ founders and the total value of Iterative companies is now worth $1.2 billion.

Our investors include Cendana, K5 Global, Village Global, Goodwater Capital with participation from a large network of Silicon Valley founders and execs including Arash Ferdowsi (Dropbox), Achmad Zaky (Bukalapak), Andrew Chen (General partner a16z, Uber), Qasar Younis (Former COO YC, Applied Intuition), David Shim (Foursquare), Kum Hong Siew (Head of Airbnb Asia), Moses Lo (Founder, Xendit), and many more.

Iterative, as an organization, has 4 distinct functions and as a result, a team for each function.

• Recruiting – Find startups for Iterative to invest in
• Investments – Decide whether Iterative should invest in a startup
• Iterative Founders – Help the founders Iterative has invested in
• Support – Make Iterative a first class organization
  
  

Iterative is currently a team of 13 and growing quickly across each of these teams.

Role Overview

The Chief of Staff at Iterative will work directly with Hsu Ken as a trusted right-hand.

In this role, you’ll have significant autonomy to solve critical problems for the organization, our community of founders and future Iterative founders. This role is critical in ensuring that the organization operates efficiently and stays aligned with its mission of supporting founders and startups. This includes, but is not limited to, designing and running Iterative’s OKR process, a new Series A program and more.

You’ll gain an in-depth understanding of how a venture capital firm operates, while working behind the scenes to keep everything running smoothly, solve complex problems, and lead cross-functional initiatives that drive both growth and cultural excellence.

Your Responsibilities

Think of yourself as both the architect and builder of our organizational infrastructure, with your role focused on three main pillars: Culture, Operations, and Strategy.

Your responsibilities will be to..

• Engineer Organizational Excellence – Design and implement scalable processes that enhance operational efficiency and drive continuous improvement.
• Create Strategic Alignment – Work closely with the team to develop and implement strategic plans, ensuring alignment across all departments and initiatives.
• Provide Decision-Making Support – Provide insights and analysis to help the organization make informed decisions, particularly in areas of strategic importance.
• Encourage Organizational Culture – Play a key role in fostering a positive, results-oriented culture that aligns with Iterative’s mission and values.
• Design and Execute on Special Initiatives – Lead or support high-impact, high-visibility special projects that drive Iterative’s long-term goals.
  
  

This role has nothing to do with managing calendars or responding to Hsu Ken’s e-mails. I can’t believe I even have to write this disclaimer.

Who You Are

We’re looking for candidates with the following characteristics.

• Comfortable with Ambiguity – You’ll often work on projects where you’ll have to figure out whether, it’s worth doing, how to measure success then how to do it. We need the type of people who can create playbooks, not just follow them.
• Systems Thinker – You view problems and solutions as part of an interconnected whole, focusing on how different parts of a system influence one another rather than isolated individual components.
• High Level of Autonomy – ****You’re a self-starter who can independently lead projects, think critically, and make sound decisions in a fast-paced environment.
• Highly Curious – ****You are a nerd. You go down rabbit holes then find more rabbit holes. You ask lots of questions and you will keep asking questions until you’re satisfied. Trick question, you are never satisfied.
• Operational Expertise – You’re process and metric-driven mindset with a track record of doing what what you say you’re going to do consistently.
• Excellent Communicator – You’re skilled in both written and verbal communication, able to effectively interface with founders, partners, team members, etc.
• Problem Solver – You’re are able to quickly identify challenges and proactively come up with creative solutions.
• Data-Driven – You have strong analytical skills with a preference for making decisions backed by data and insights.
• Adaptable – You are comfortable in a fast-paced, constantly evolving environment, able to pivot quickly based on new information or changing priorities.
• Leadership – Proven leadership experience with the ability to manage and inspire teams while working cross-functionally across the organization.
• Experience with Startups – Ideally, you have worked at or on a startup before.
  
  

Although not necessary, this role is especially good for people who’ve been a founder, operator or might want to be a founder in the future.

Culture

These are the Iterative values. They’re not for everyone but if they speak to you, you might be just what we’re looking for.

• Iterate or Die – We take this literally. Ship early, get continuous feedback, and boldly experiment. If not the organization will die.
• Empathy is Our Competitive Advantage – Our success depends on our ability to empathize with other people in the organization and the community.
• Be Realistically Ambitious – The best strategy for making a big impact is to be realistic, have a plan and be ambitious.
• Responsibility is a Privilege, Not a Right – Being part of Iterative means being given responsibility for a part of our business. Be a good steward of that responsibility by being accountable, diligent and open-minded.
  
  

Note: Although you might see this role posted in multiple locations, it’s a single headcount. We’re a fully remote team, but due to LinkedIn’s setup, we need to specify a city for each job posting.