Chief of Staff

About Propseller

In January 2023, Propseller has been ranked #10 in Singapore’s fastest-growing companies 2024 ranking by The Straits Times and Statista. In August 2022, Propseller raised a US$12M Series A led by Vertex Ventures, the VC arm of Temasek, the investment company owned by the Government of Singapore and the Series A lead investor of Grab.

Propseller’s mission is to help people build wealth with real estate. We’re building an end-to-end real estate transaction platform and towards that goal, we started the journey by building a technology-powered real estate brokerage that is valuable, reliable and fairly priced.

By elevating the most human part of the service with top in-house agents and industrializing all the rest with technology and centralized operations, we became Singapore's most loved real estate agent with an average Google My Business rating of 4.7/5 (500+ reviews).

The next phase of the journey is to go from helping people sell their homes to becoming the No1 brand for people to move from one home to the next: sell, buy, and finance.

Find out more at: propseller.com/careers/

Role Description

Reporting directly to our Chief Executive Officer, the Chief of Staff (”CoS”) is a highly talented and committed individual helping the CEO to connect vision with execution by driving the operating mechanisms of the organisation.

Acting as a strategic partner and a trusted advisor, you are one of the most connected individuals of the organisation and the champion of transversality. You drive strategy and operating systems for the organisation. You own cross-functional and special projects. You run the office of the CEO, including internal communication, investors relations and day-to-day operations.

With plans to grow our team from 75 to 200 over the next 24 months on the back of our Series A, this role is an amazing opportunity for an associate/mid-senior level high potential individual to be at the forefront of exponential growth alongside the executive team. Being Propseller Chief of Staff for 24 months is worth 10x more than any ivy league MBA.

Some famous Chief of Staff (CoS):

• In “House of Cards”, Doug Stamper is the CoS of Frank Underwood
• Before being French president, Emmanuel Macron was deputy-CoS of Francois Hollande
• Propseller Vice President of Sales, Jeong Lee, was Propseller’s first Chief of Staff

Duties & Responsibilities

• Develop Full-Stack StrategyResearch: Feed executive team with strategic research and insights and fuel the long-term strategy of the company;
  Planning: own and coordinate annual/quarterly strategic planning including financial modelling, both with the executive team and the board;
  Alignment: with functional leaders and managers, align the entire company with ownership of OKRs and high level performance reporting;
  
• Own Cross-Functional and Special ProjectsIndependently own cross-functional company projects;
  Incubate new functions that don’t fall neatly into any existing teams;
  Solve critical issues, or crisis as they arise.
  
• Run CEO’s OfficeOperating System: improve and scale our decision making system, how we run meetings and how we get things done as a team;
  Communication: For internal communication, set direction and frequency of internal communications. Draft written communication and oversee company-wide events (all hands, retreat). For external communication, develop draft presentations and investor updates, including preparation of quarterly board meetings;
  Leverage CEO’s Impact: Facilitate and follow up on critical meetings and tasks such as executive team meetings, all hands meetings, or critical projects. Review documents on behalf of the CEO and prepare CEO’s key meetings. Act as the sparring partner of the CEO.
  

Ideal Candidate

This is a role for you if you are a very high potential currently at a associate/mid-senior level in consulting, investment banking/VC, or a high-growth start-up. You are deeply passionate about cross-functional project management, high-level thinking, and on-the-ground execution. You are counted on as a thought leader in your current role because you can download a huge amount of information and synthesize a vision out of it into a plan that drives stakeholders’ engagement 360 degrees.

You are extremely organized and very good at getting things done, systematically. You are ready and not afraid to do everything: working on your own projects at 9 am, fixing a bug in the operating plan model at 10 am, picking up dry cleaning of your CEO at 11 am, and pitching a VC partner at noon. At this stage of your career at least, you are looking for accelerated learning but you are comfortable being in a role that has a huge impact yet almost no spotlight.

We expect the CoS to commit to the role at least 18 months before moving on to another role. With 18 months or more of accelerated strategic and holistic learnings, you’ll be an ideal candidate to lead a function, or geography, with or without an intermediary role. Our latest Chief of Staff, Jeong Lee, was promoted to VP of Sales, leading a team of 30+ people, after only 15 months as Chief of Staff.

Requirements

• Bachelor's Degree from a top-tier university;
• 4 years of working experience in top-tier management consulting, investment banking, or VC or in the strategy or project management function of a technology company;
• High analytical and problem-solving abilities;
• Mastery of spreadsheet-based modelling and analysis;
• Strong written and verbal communication skills;
• Detail-oriented enough to produce documentation for senior stakeholders;
• Demonstrated success in managing complex, cross-functional projects;
• Extremely versatile and able to temporarily jump into any senior role when required;
• Highly structured and organized with the ability to build systems from scratch;
• Ability to think critically and autonomously about various disciplines and domains;
• Empathy and emotional awareness are required to lead with influence.

You Get

• Central, iconic office near Lavender, Bendemeer, and Farrer Park MRTs;
• Be involved in strategic decisions that make a real impact and get involved in the day-to-day running of a Series A start-up;
• Opportunity to be propelled into a senior role after 18-24 months;
• State-of-the-art-tools: MacBook Pro, Jabra Headset, fully-integrated CRM, etc;
• One to two days home-office per week after on-boarding;
• Opportunity to make history and help thousands of people with the biggest financial decision of a lifetime.

Recruiting Process

Ideal length: 3 weeks

If your application is selected:

1. Interview 1: Video Call: Introductory call with HR Director
2. Case 1: Prepare case at home, then submit
3. Interview 2 - Video Call: Case 1 presentation and discussion with VP Sales (ex Chief of Staff)
4. Case 2: Prepare case at home, then submit
5. Interview 3 - Physical: Case 2 presentation and discussion with CEO
6. Interview 4 - Physical: Interview with Head Propseller Buy + Head of Propseller Premier
7. Reference Check
8. Welcome aboard!