Chief of Staff, Office of the CEO

About the role

This position is designed for an individual who will operate as a direct force multiplier for the CEO, owning the most complex and interdisciplinary challenges that the company faces on a daily basis. The hire will ensure the smooth and efficient operation of the business, allowing the CEO to focus on strategic leadership and external growth initiatives. You are expected to move beyond support and into execution, taking full ownership of problems that span product, operations, and strategy to guarantee that the company runs well and WINS! This role demands extreme ownership where you will be the first to dive into unfamiliar domains, rapidly synthesize information, and drive initiatives from conception to completion without constant direction. You will be a key part of the executive team, providing critical thinking and operational rigor to navigate high-stakes scenarios.

Key facts

What you'll do

You will shadow the CEO extensively to absorb the intricate mechanics of the business, attending executive team meetings, external pitches, and product workshops while traveling to visit partners and customers to build a comprehensive contextual understanding. You will rapidly synthesize this information to solve your first problem, taking something significant off the CEO's plate, which could involve rebuilding an operational process, designing a new product feature, or creating an entirely new business line. As you prove your capability, you will take on problems of increasing complexity and impact, potentially falling in love with a specific area of the company and transitioning into it full-time or helping to launch a new business line that defines the future of the organization. You will utilize writing as a primary tool to think precisely and clarify messy problems, ensuring that all solutions are well-documented and strategically sound. You will apply analytical reasoning while remaining comfortable with intuition, balancing data-driven decisions with gut instincts derived from deep immersion in the business. You will move with speed and default to ownership, feeling a sense of pain when something is not working and possessing an almost compulsive drive to fix it immediately. You will exercise technical thinking as a core methodology, treating technology not as a store of knowledge but as a way of processing and solving business challenges at scale. You will uphold a standard of humility, recognizing that the greatest solutions often come from understanding limits and leveraging the collective intelligence of the team.

Requirements

You must possess intellectual vitality, demonstrating an endless curiosity about how to build a great business and understanding the interplay between finance and technology in the modern economy. You need to be extremely driven, motivated to build an amazing company and an incredible career simply because you love seeing what you are capable of achieving under pressure. You are required to have 5+ years of experience doing hard things, which can be accumulated through consulting, banking, engineering, product management, operations, founding a company, or taking over a family business that taught you resilience. You must be analytical and not afraid of data, while also possessing the ability to think intuitively when data is incomplete or ambiguous. You must use writing as a precise tool to clarify complex problems and communicate solutions effectively to diverse stakeholders. You need to be technically proficient, understanding that technical acumen is a way of thinking and problem-solving rather than merely possessing a specific store of knowledge. You are expected to move quickly and take ownership by default, feeling an immediate compulsion to fix issues the moment you perceive that something is not working well. You must demonstrate humility, acknowledging when you do not have all the answers and being open to feedback and collaboration. You must be located in San Francisco, as this role requires physical presence in the office to collaborate effectively with the executive team. You must be available for a full-time engagement, committing to long hours and a schedule that often includes weekends, as winning requires a level of intensity and dedication that is unwavering. You must be prepared to face problems outside your current area of expertise, requiring a rapid learning mindset and continuous improvement to thrive in this environment.

Nice to have

There are no preferred items listed in the SOURCE beyond the core requirements and role expectations.

Practical notes

This role requires full-time on-site work in San Francisco, with additional benefits provided to those who choose to work from the office. The position involves long hours, including frequent evenings and Sundays, though Saturdays are typically off. Relocation assistance is available for candidates who qualify and require it to move to the San Francisco office.