The Chief of Staff (CoS) role has become increasingly prevalent in technology startups, particularly in the United States. While the position originated in government, it has evolved to become a mainstay in the tech industry, with companies like dYdX, LaunchDarkly, and Check hiring for this role. The Chief of Staff is often described as a “super-connector” and a “jack of all trades” within the startup ecosystem.

The role is often mysterious, constantly evolving, and amorphous, which provides unique learning opportunities for those who take on the position. It is an opportunity to serve as an “apprentice” to a respected founder, gaining valuable insights from the CEO’s vantage point.

Origin and Evolution of the Chief of Staff Role

The Chief of Staff role has its roots in government, with fictional characters like Leo McGarry from “The West Wing” popularizing the position. In recent years, the role has become increasingly common in US tech companies, and it is now gaining traction in Australia and New Zealand as well.

As startups grow and scale, the responsibilities of the Chief of Staff evolve. In early-stage companies, the role tends to be more operational and tactical, focusing on managing internal workstreams and processes. As the company matures, the Chief of Staff’s role becomes more strategic, driving special projects and initiatives that support the company’s growth.

Key Characteristics of a Startup Chief of Staff

A successful Chief of Staff in a startup is often described as a jack of all trades and a super-connector. They must be able to navigate the ambiguity and constant change that comes with working in a fast-paced, high-growth environment. The role requires a strong generalist skillset, with the ability to quickly learn and adapt to new challenges.

Building trust with the CEO and other executives is crucial for a Chief of Staff’s success. They must be able to effectively communicate the company’s vision, priorities, and initiatives to both internal and external stakeholders. A Chief of Staff should also be proactive in identifying and solving problems, always looking for ways to make their principal more effective.

Core Responsibilities of a Startup Chief of Staff

The responsibilities of a Chief of Staff can vary widely depending on the company’s size, stage, and industry. However, there are three core areas where a Chief of Staff typically focuses their efforts:

Providing direct support to the CEO
Managing internal workstreams and processes
Driving special projects and strategic initiatives

Providing Direct Support to the CEO

One of the primary responsibilities of a Chief of Staff is to provide direct support to the CEO. This often involves calendar management, ensuring that the CEO’s time is prioritized and optimized. The Chief of Staff also serves as a trusted advisor, helping the CEO navigate key decisions and communicate effectively with internal and external stakeholders.

In addition to supporting the CEO, a Chief of Staff may also work closely with other C-level executives, such as the CMO or CPO. They act as a liaison between the executive team and the rest of the organization, ensuring alignment and effective communication across all levels.

Managing Internal Workstreams and Processes

A Chief of Staff is often responsible for managing internal workstreams and processes, ensuring that the company operates efficiently and effectively. This may involve:

Preparing agendas and materials for company all-hands meetings
Coordinating board meeting prep and investor updates
Ensuring that planning cycles, such as OKRs and budgeting, run smoothly
Documenting and tracking learnings to compound knowledge and insights

By creating and maintaining effective systems, a Chief of Staff can help scale their impact and make themselves obsolete in certain areas, allowing them to focus on higher-level strategic initiatives.

Driving Special Projects and Strategic Initiatives

A Chief of Staff is often tasked with driving special projects and strategic initiatives that are critical to the company’s growth and success. These projects may include:

Fundraising and investor relations
International expansion
Supporting the risk & fraud organization
Assisting with sales enablement and marketing efforts

In these roles, a Chief of Staff must be able to navigate ambiguity, think strategically, and execute effectively. They must balance between executing tasks and strategizing to add value to the organization.

Essential Skills for a Successful Startup Chief of Staff

To be successful in a Chief of Staff role at a startup, several essential skills are required:

Navigating Ambiguity and Change

Startups are known for their fast-paced, ever-changing environments. A Chief of Staff must be comfortable navigating ambiguity and adapting to change. They should be able to quickly assess situations, make decisions with limited information, and pivot when necessary.

Staying nimble is key to coping with the constant change that comes with working in a startup. A Chief of Staff should constantly evolve and focus on “how” they work to drive success in their role.

Proactive Problem-Solving and Execution

A successful Chief of Staff is proactive in identifying and solving problems. They should always be looking for ways to optimize workflows, enhance their principal’s impact, and drive the company forward.

Execution is equally important. A Chief of Staff must be able to take high-level strategies and break them down into actionable steps, ensuring that initiatives are implemented effectively and efficiently.

Effective Communication and Relationship Building

Communication is a critical skill for any Chief of Staff. They must be able to clearly articulate the company’s vision, priorities, and initiatives to both internal and external stakeholders. This requires strong written and verbal communication skills, as well as the ability to adapt their communication style to different audiences.

Building relationships and trust is also essential. A Chief of Staff must invest in building strong relationships with the executive they support, as well as other key stakeholders throughout the organization. This trust is crucial for effective collaboration and decision-making.

Landing a Chief of Staff Role at a Startup

If you’re interested in pursuing a Chief of Staff role at a startup, there are several factors to consider:

Understanding Executive Expectations

When seeking a Chief of Staff position, it’s important to focus on the executive you will be supporting and their expectations for the role. Each executive will have different needs and priorities, so it’s crucial to understand what they are looking for in a Chief of Staff.

Some executives may prioritize operational support, while others may be more focused on strategic initiatives. Understanding these expectations upfront can help ensure a good fit between the Chief of Staff and the executive they support.

Ideal Chief of Staff Candidate Profile

While the ideal profile of a Chief of Staff candidate can vary depending on the company and executive, there are some common traits and experiences that are often sought after:

Professional services experience, such as consulting or investment banking
Startup experience, either in an operational or strategic role
Strong generalist skillset, with the ability to quickly learn and adapt
Specific expertise in an area that aligns with the company’s needs, such as finance, operations, or product management

Aspiring Chief of Staffs can benefit from resources like Maggie Hsu’s blog series, “The Great CEO Within” handbook, and “The Gatekeepers” book. Programs like On Deck’s Chief of Staff course and fellowship can also provide valuable training and networking opportunities.

Ultimately, landing a Chief of Staff role at a startup requires a combination of the right skills, experiences, and fit with the executive and company. By understanding the expectations, developing the necessary skills, and leveraging available resources, aspiring Chief of Staffs can position themselves for success in this dynamic and impactful role.

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