Why the Chief of Staff is Important for a Startup

Startup founders and practitioners are often debating the best actions to take and decisions to make in their early-stage companies. Determining the right hires has been a major part of this conversation. The hot topic on the table lately has been around hiring the role of Chief of Staff. There is a growing conversation about whether startup leaders and founders should hire a Chief of Staff (COS), and here at Visible, we believe it is one of the most important hires you can make.

A Chief of Staff is essential for your startup because their role is designed to be an extension of the c-suite’s leadership and strategy. Their role allows companies to scale faster and more strategically. Between the Board of Directors, Executive Board, stakeholders, and employees, startups have a lot of moving parts, and a Chief of Staff can be the cog in the machine that makes all those pieces work smoothly together.

A Chief of Staff is the right-hand person to an executive team member, typically the CEO or COO. The COS is tasked with managing the executive’s goals, priorities, internal and external operational tasks, and special strategic projects as needed.

The typical responsibilities included in a Chief of Staff role may include:

Managing Executive Goals and Priorities

A Chief of Staff helps determine what optimized time really looks like. For CEOs and COOs, there is plenty of work that could easily fill the day. But what work is most important for business development and moving the business forward? A Chief of Staff helps direct the decision-making and serves as a sounding board for the CEO, owning the task of keeping the executive aligned to the goals he or she set forth to push the business forward. A COS considers these executive goals and even formalizes them in a framework such as the OKR (Objective Key Results) framework. With these executive OKRs formalized, a COS helps guide the CEO/COO’s priorities day over day.

Operational Tasks

With specific areas of work, including board meetings and other critical decision-making sessions or meetings on the agenda, the Chief of Staff helps manage these priorities by handling operations tasks like agenda setting and distribution, communications with teams across the startup to gather insight and updates on various company-wide priorities and progression. Not only will a Chief of Staff work on internal operational tasks like meeting prep, gathering updates, and tracking company progress towards goals, but they also tend to handle external operational tasks as well. These external operational tasks might include sending investor updates to stakeholders, serving as the point of contact to the Board of Directors representing the CEO’s office, or even working on communications and PR.

Special Strategic Projects

Startups move fast, and different priorities and special obligations come up for leadership out of the blue. Additionally, as your startup goes through strategic growth periods like fundraising or even acquiring smaller startups down the line, the priorities of a CEO’s time will greatly change. These strategic times are the perfect way to utilize a COS. If fundraising is going to take up a significant chunk of a CEO’s time, a Chief of Staff can step in and manage aspects of that strategic task such as deck assembly, overview materials for the potential investors, and communication with parts of the business that need to deliver information for said fundraising presentation.

Chief of Staffs are typically very versatile in their skill set, with communication, strategic thinking, and analytical skill sets. This background makes them the perfect person to take on roles that require strategic thought and concise summaries but are potentially too time-constraining for a CEO to dedicate all of their energy to. With their unique mix of hard and soft skills, executive insight, and strategic position in the company, a COS is a major value-add to any startup. Our team at Visible has identified seven primary ways that a Chief of Staff can strengthen your startup.

When is it Time to Hire a Chief of Staff?

Determining the right moment to bring a COS into your startup is crucial for maximizing their impact. By recognizing the following indicators and acting promptly, startups can leverage the unique skills and perspectives that a Chief of Staff brings to the table, ensuring sustained growth and success.

Related resource: How to Hire Your First 10 Startup Employees

Here are some key indicators that it might be the right time to hire a COS:

Leadership Bandwidth is Strained

As your startup grows, the demands on the leadership team increase exponentially. This strain manifests as longer work hours, difficulty in prioritizing tasks, and a constant feeling of being overwhelmed. Executives may find themselves bogged down with operational details rather than focusing on strategic initiatives. A Chief of Staff can help alleviate this burden by managing critical tasks, streamlining decision-making processes, and allowing leaders to focus on high-level strategic goals. They act as a force multiplier, extending the reach and effectiveness of the leadership team.

A Need for Cross-Departmental Collaboration

Effective cross-departmental collaboration is essential for startups to innovate and scale. However, as the organization grows, silos can form, and communication breakdowns can occur. This can lead to inefficiencies, duplicated efforts, and missed opportunities. A Chief of Staff ensures seamless collaboration by facilitating communication between departments, aligning goals, and overseeing cross-functional projects. They help to break down silos and ensure that all parts of the organization are working towards the same objectives.

Related resource: How to Build Organizational Alignment Easily

Mergers, Acquisitions, or Product Launches

Significant events like mergers, acquisitions, or major product launches require focused attention and meticulous coordination. These initiatives bring unique challenges such as integrating new teams, managing extensive paperwork, and aligning strategies. A Chief of Staff can manage these complex processes, ensuring that all aspects are covered and that the executive team can concentrate on high-level strategic decisions. They provide the necessary oversight and coordination to make these critical events successful.

Leadership Succession Planning

Succession planning is vital for maintaining continuity and stability within the leadership team. It involves identifying and developing future leaders within the organization. However, amidst the daily hustle of running a startup, this can often be neglected. A Chief of Staff plays a crucial role in leadership succession planning by mentoring potential leaders, overseeing development programs, and ensuring there is a clear plan for leadership transitions. This not only secures the future of the company but also helps in retaining top talent by providing clear career progression paths.

Typical Responsibilities for a Chief of Staff

A Chief of Staff in a startup wears many hats, acting as a strategic partner to the CEO or COO. Their role involves a wide range of responsibilities that help streamline operations, drive strategic initiatives, and ensure that the leadership team can focus on high-priority tasks. Below are some of the key responsibilities that a Chief of Staff typically handles, each of which will be covered in more detail in their respective sections.

Managing Executive Goals and Priorities

A Chief of Staff helps determine what optimized time looks like for the executive team. For CEOs and COOs, there is plenty of work that could easily fill the day. But what work is most important for business development and moving the business forward? A Chief of Staff directs the decision-making process, ensuring that the executive's time is spent on tasks that are crucial for growth. They serve as a sounding board for the CEO, aligning the executive with the company’s strategic goals and formalizing them using frameworks such as OKRs (Objectives and Key Results). This helps guide the CEO/COO’s priorities day by day.

Operational Leadership

The Chief of Staff manages both internal and external operational tasks, ensuring smooth day-to-day operations. This includes setting agendas for board meetings, gathering updates from various teams, and tracking progress towards company goals. They handle communications across the startup to ensure everyone is aligned with the company’s priorities. Externally, they might send investor updates, serve as a point of contact for the Board of Directors, and manage public relations tasks. By overseeing these operational details, the Chief of Staff allows the executive team to focus on more strategic issues.

Strategic Projects

Startups often encounter special strategic projects that require focused attention. Whether it’s fundraising, a product launch, or an acquisition, a Chief of Staff manages these projects, ensuring they align with the company’s strategic goals. They take on roles that require strategic thinking and concise summaries, handling aspects such as preparing decks for investors, assembling materials for presentations, and coordinating communication across the company. This enables the CEO to concentrate on core business functions without getting bogged down by the intricacies of these special projects.

Important Skills for a Chief of Staff to Have

When making the strategic hire of a Chief of Staff, startup founders need to look for specific skills that will ensure the candidate can effectively support the leadership team and drive the company forward. These skills serve as crucial filters and green flags in the interview process, guiding founders on how to frame their questions and identify the best candidate for their organization.

Strategic Thinking

Strategic thinking is vital for navigating the complexities of a growing startup. A Chief of Staff must be able to anticipate future challenges, identify opportunities, and develop long-term plans that align with the company's vision. By outsourcing strategic thinking to a Chief of Staff, the executive team can ensure that someone is always focused on the bigger picture, allowing them to concentrate on immediate operational needs. This skill is essential for maintaining a clear direction and ensuring the startup's long-term success.

Project Management

Effective project management is crucial for keeping various initiatives on track and within budget. A Chief of Staff must be adept at coordinating multiple projects, setting deadlines, and ensuring that resources are allocated efficiently. In a growing startup, where rapid execution is key, outsourcing project management to a Chief of Staff ensures that projects are completed on time and meet the company's strategic objectives. This allows the executive team to focus on higher-level strategic decisions without getting bogged down in the details of project execution.

Analytical Skills

Analytical skills enable a Chief of Staff to interpret data, identify trends, and make informed decisions. In a data-driven startup environment, these skills are critical for providing valuable insights that inform strategic direction and operational improvements. By outsourcing analytical tasks to a Chief of Staff, the executive team can ensure that decisions are based on solid data and analysis, reducing the risk of errors and improving overall efficiency.

Communication Skills

Strong communication skills are necessary for a Chief of Staff to act as a liaison between the executive team and other departments. They must be able to convey complex ideas clearly, facilitate effective meetings, and ensure that all stakeholders are on the same page. Good communication helps maintain transparency, fosters a collaborative work environment, and ensures that everyone in the organization is aligned with the company's goals. By outsourcing communication management to a Chief of Staff, the executive team can ensure that information flows smoothly and efficiently throughout the organization.

Ways a Chief of Staff Can Strengthen Your Startup

A Chief of Staff can significantly enhance the effectiveness and efficiency of a startup. By taking on critical tasks and responsibilities, they enable the executive team to focus on strategic goals and high-priority items. Here are some of the ways a Chief of Staff can strengthen your startup:

Focus on Priority Items

The day-to-day life of a CEO or COO can be extremely hectic, with numerous decisions and tasks competing for their attention. A Chief of Staff helps manage these priorities by filtering out less critical tasks and directing the executive’s time towards the most strategic decisions that align with the company's OKRs (Objectives and Key Results). This ensures that the leadership focuses on what truly drives the business forward while the Chief of Staff handles smaller issues and routine decision-making.

Facilitate Smooth Information Sharing

Effective communication is crucial for the smooth operation of a startup. A Chief of Staff acts as a central point for gathering and disseminating information across the organization. They collect updates from various departments, distill the most important points, and present a contextualized executive summary to the CEO. This process ensures that the CEO receives all the necessary information without being overwhelmed by details, and that communication flows smoothly from the CEO to the rest of the company.

Inform Strategy and Decision-Making

A Chief of Staff serves as a valuable resource for keeping the executive team connected to the various happenings across departments. By providing an executive summary of company-wide updates, a Chief of Staff helps the leadership team make informed strategic decisions more quickly. They ensure that all relevant information is considered, facilitating better and faster decision-making processes.

Maximize Time While You Scale

As a startup scales, the demands on the executive team’s time increase. A Chief of Staff helps maximize this time by prioritizing tasks and focusing on critical projects. They handle routine and operational tasks, allowing the CEO to dedicate more time to deep-think projects and strategic initiatives. This ensures that the leadership’s time is used efficiently, even as the company grows and evolves.

Tackle Special Projects

Special projects, such as fundraising rounds, product launches, or industry presentations, require focused attention and dedicated resources. A Chief of Staff is perfectly positioned to spearhead these projects, managing aspects such as preparing investor decks, assembling materials for presentations, and coordinating communication across the company. This allows the CEO to stay focused on daily priorities while still ensuring that special projects are executed effectively.

Provide Oversight and Perspective

Startups can often become echo chambers where new perspectives are hard to come by. A Chief of Staff, especially one with experience from other startups, brings a fresh viewpoint to the c-suite. They provide oversight and serve as a sounding board for new ideas and strategies, helping to ensure that the company stays innovative and adaptable.

Push the Business Forward

Ultimately, a Chief of Staff is a strategic player in moving the business forward. They streamline operations, manage strategic projects, and ensure effective communication, all of which contribute to the company’s growth. By freeing up the executive team to focus on high-level strategic goals, a Chief of Staff helps take a startup from good to great and potentially to unicorn status.

Chief of Staff vs Executive Assistant

Understanding the difference between a COS and an Executive Assistant (EA) is crucial for startup founders to ensure they make the right hire at the right time. While both roles support the executive team, they do so in different ways and with distinct focuses.

Chief of Staff

A Chief of Staff is a strategic partner to the executive team, particularly the CEO or COO. Their responsibilities are broad and focus on aligning the company’s strategic goals with daily operations. Here are some key aspects of the COS role:

Strategic Focus: The COS works on high-level strategic initiatives, ensuring that the executive team’s vision and goals are implemented across the organization.
Project Management: They handle complex projects that span multiple departments, such as mergers, acquisitions, product launches, and fundraising efforts.
Decision-Making Support: The COS provides critical insights and data analysis to support executive decision-making, helping to inform strategy and operational improvements.
Cross-Departmental Collaboration: They facilitate communication and collaboration between different departments to ensure everyone is aligned and working towards common goals.
Leadership Development: The COS often plays a role in leadership succession planning and mentoring potential future leaders within the organization.

Executive Assistant

An Executive Assistant, on the other hand, focuses on optimizing the executive’s daily schedule and administrative tasks. Here are some key aspects of the EA role:

Administrative Focus: The EA manages the executive’s calendar, schedules meetings, handles correspondence, and organizes travel arrangements.
Time Management: They ensure that the executive’s time is used efficiently by prioritizing meetings and tasks, allowing the executive to focus on their most important responsibilities.
Task Coordination: The EA handles a variety of administrative tasks that help keep the executive’s day running smoothly, from booking appointments to preparing documents.
Support Role: They provide general support to the executive, ensuring that they have everything they need to perform their duties effectively.
Routine Operations: The EA is instrumental in managing routine operational tasks, allowing the executive to concentrate on more strategic issues.

Key Differences

Scope of Responsibilities: The COS has a broader, more strategic scope, focusing on aligning and implementing the company’s long-term goals. The EA’s scope is narrower, concentrating on the day-to-day administrative support of the executive.
Strategic vs. Administrative: The COS is involved in strategic decision-making and high-level project management, while the EA handles administrative and logistical tasks.
Cross-Departmental Impact: The COS often works across departments to facilitate collaboration and ensure alignment with company goals. The EA typically works closely with the executive and less so with other departments.
Long-Term vs. Short-Term Focus: The COS is focused on long-term strategic initiatives and projects that drive the company forward. The EA is focused on the immediate, short-term needs of the executive.

Making the Right Choice

For startup founders, deciding between hiring a Chief of Staff and an Executive Assistant depends on the company’s current needs and stage of growth:

If the company needs high-level strategic support, project management for complex initiatives, and cross-departmental coordination, hiring a Chief of Staff is the right choice.
If the primary need is managing the executive’s schedule, handling administrative tasks, and ensuring day-to-day operations run smoothly, then an Executive Assistant is the appropriate hire.

Equipping a Chief of Staff for Success at a Startup

To ensure a COS is successful at your startup, it's crucial to clearly define their role and responsibilities from the outset. This includes creating a detailed job description that outlines specific tasks and expectations. Additionally, providing a comprehensive onboarding process with clear goals and KPIs will help the COS integrate smoothly and start contributing effectively. Regular check-ins and feedback sessions will also ensure they are aligned with the company’s strategic goals and can adjust to any evolving needs.

Equipping your COS with the right tools and resources, fostering open communication, and maintaining a supportive environment will enable them to execute their duties effectively. This preparation ensures that the COS can focus on driving strategic initiatives and managing critical projects, ultimately contributing to the startup’s growth and success.

How Visible Can Help

Visible offers a range of tools and resources designed to support Chief of Staffs in their roles, making it easier to streamline executive and investor communications.

With features that facilitate data tracking, reporting, and stakeholder updates, Visible ensures that your Chief of Staff can efficiently manage information flow and keep everyone aligned with the company’s strategic objectives. By leveraging Visible's platform, startups can enhance their operational efficiency, improve decision-making processes, and ultimately drive growth.

For more information about how Visible helps Chiefs of Staff streamline their executive and investor communications, learn more here.