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A comprehensive explanation about the role, career stages and trajectory of a Chief of Staff.
Put together by the Chief of Staff School team as a guide for aspiring and current Chiefs of Staff, hiring principals and recruiters.
The Chief of Staff (CoS) is a strategic generalist to the principal of an organization, usually the CEO. He or she plays a multifaceted role in supporting leadership decisions and bridging cross-functional strategic execution to achieve organizational impact. In startups or enterprises, they are the right-hand person to the CEO or Founder, tailored to the leader’s specific needs.
No one CoS is the exact same. The roles and responsibilities of a CoS are highly contextual to the strategic support the principal need in the organization at that specific point of time. The type of organization (for profit or non-profit), business stage, industry, and leadership style of the principal are some other factors that have direct influence on what kind of CoS role the principal will need to drive organizational success together.
In general, the role of a CoS resolves around facilitating for strategic coordination, key information flow, and goal alignment across functional units to achieve organizational objectives. They also temporarily fill in business function gaps, making them valuable assets to any organization’s operations as an enabler and orchestrator.
A trusted and high caliber CoS to a CEO is someone deeply knowledgable about the ins and outs of the organization – an all rounder shadow CEO that can keep the ship running without the presence of a CEO. They also serve as a sounding board and a confidant to the principal.
CoS typically do not have dedicated financial or talent resources under management, emphasizing their agility and resourcefulness for organizational success.
Commonly seen in traditional non-tech enterprises where they serve as “generals” to the CEO or business owners that carry the primary responsibility for driving the business forward.
At later-stage startups or larger enterprises where the CEO requires a team of strategy-focused analysts and researchers to support key company- wide business decision-making processes.
The Chief of Staff (CoS) is commonly compared to other roles that are more operational and generalist in nature, such as the Chief Operating Officer, Chief Human Resource Officer, and Executive Assistant. While they may be equipped with functional skill sets and serve in a strategic role to the principal, there are significant differences.
The most significant difference between an Executive Assistant and a CoS lies in the level of involvement each has in assisting the principal in making strategic decisions, as well as the breadth of their operational understanding of the entire business model. Consequently, a CoS is capable of serving as a strategic sounding board for his/her principal.
It is easily confused because both of them are confidant to the principal and they have control over the principal’s calendar and schedule.
Three key domains distinguish the CoS from classical human resource executives.
First, there is a difference in the level of familiarity with the leadership and decision-making style of the principal. Second, there is a distinction in the level of operational involvement. The CoS is typically in a contextually advantageous position when it comes to assisting in the recruitment process for the principal, identifying talents that may be suitable for specific roles directly associated with the principals, such as C-level or highly strategic hires. Despite this, the CoS collaborates closely with human resource executives for administrative and management processing. Thirdly, the Chief of Staff is instrumental in assisting the principal in developing organizational culture by enabling cross-functionally executions. They make excellent candidates for the position of Chief People Officer.
Chief of Staff
CEO
BOARD/INVESTORS
TEAM MEMBERS
VP/CXO
STARTUP
SEED
A close-knit team with a flat organization structure. Team members tend to be more “self-directed” in aligning tasks to Founder/CEO’s vision and business priorities
Typically, the Chief of Staff (CoS) is the first business hire and a vital member of the founding team. They thrive in and are adept at:
SERIES-A
Considerably flat organization joined by more specialists. Specialists tend to “organically” group together to achieve business goals – creating ad-hoc “task forces” or project team
When product-market-fit has achieved and scaling is the key priority of the organization, the CoS should be comfortable with parachuting in and taking ownership by:
SCALE-UP
SERIES-B
A hierarchical organization starts to form when “organic” working groups are formalised into fully-fledged specialised business units and/or departments
A highly effective CoS excels in cross-functional communication and delegation, demonstrating proficiency by:
SERIES-C/BEYOND
The organization is made up of departments with “managers” above managers exist to ensure strategic decisions and plans are effectively cascaded downward for execution
During the transitional state of a scale-up to a full-fledge corporate enterprise, a CoS stands closely with the CEO by:
CORPORATE
A highly hierarchical and structured organization supported by centralized functions and established bureaucratic processes
For large multinational enterprises, a CoS is capable of assuming a dedicated ‘head of people’ role for technical CXOs in specific business units or verticals by:
An experienced CoS is like a highly capable Swiss Army knife. You are likely to be valuable in multiple areas, which is a luxury that Strategic Generalists possess. Your options are broader compared to Specialists. What comes next depends on your self-awareness, desired career direction, and potentially on the Principal and organizational stage that can amplify with you.
You can…
The CoS School is co-created by a team of former global tech startup operators and venture community builders at GUIDE in partnership with Ask A Chief of Staff. Our mission is to democratize and institutionalize the essential generalist skill set needed to shape the diverse and inclusive innovative enterprises of tomorrow.
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