About the Chief of Staff role

I’ve created an introductory outline to help others discuss the role of the Chief of Staff in the context of Seed and Series A+ startups. Please note that what is standard (practice, tenure, etc.) may not apply 1:1 in every instance, but is a starting point for shared understanding of the nature of the role across different types of startups and larger organizations.

Most of what I have included here is my own, some language (including key terms) is borrowed, and in a couple of instances I have quoted directly from source material, i.e. “Questions for the principal…” Cheers!

Table of Contents

• About the Chief of Staff role
• Table of Contents
• Why Chief of Staff
• Scope & Directives
• Process, People and Portfolio
• Principal, Senior Leadership, and Organization
• First 90 Days
• Role Development
• Talents, Routines & Motivations
• Resources

Why Chief of Staff

The Chief of Staff is chartered to serve the principal, helping bring order amidst increasing complexity and operating in highly ambiguous environments. Its primary goal is to enable the executive to scale; further to optimize outcomes across senior leadership teams; and later, org-wide growth and development.

Scope & Directives

The day-to-day responsibilities of a Chief of Staff depend on the size, industry, structure, and priorities of the company, as well as the nature and priorities of the principal(s) they serve. It is a rapidly evolving role, with areas of focus that can swing dramatically from month to month, while always maintaining a core set of continuous responsibilities. As such, the role is highly varied, not serving an explicit function, but rather supporting functional development across or within a business unit(s), function(s), or capacity as needed.

Process, People and Portfolio

Chiefs of Staff contributions can be viewed through three main scopes: process, people and portfolio.

Process scope: Evaluate, manage or improve key corporate process, enabling optimal operating conditions, process efficiency and bottom line gains.

• Examples can include coordination of annual planning and managing quarterly OKR’s on behalf of the principal as an interface with divisional leadership, helping the CEO prepare and execute board meetings, developing improved practice for weekly all hands and or other meeting formats, etc.

People scope: A conduit and proxy for the principal to be ‘present’ across internal teams, addressing issues or morale, culture and productivity; work with the people function/HR.

• Examples can include company-wide initiatives or cultural surveys and followup actions, hiring and onboarding or offboarding support of talent, coordinating growth-focused team and leadership offsites, delegation attendance to industry events, etc.

Portfolio scope: Owning or supporting projects advancing the strategic goals or the organization, its business units, or senior leadership initiatives.

• Examples can include contributing to product launch or line expansion, overseeing go-to-market motions, as point contact for external partnerships, leading user and market research studies, etc.

Principal, Senior Leadership, and Organization

Chiefs of Staff have three main orientations: towards the principal, senior leadership teams, and organization.

Stage 1 directive — Orientation towards the principal

• Early focus on expanding the capacity and output of the principal and associated functions, developing personal rapport and trust, and based off of early deliverables and wins relevant to first <6 months priorities
• Includes optimizing principal’s time, accompany meetings, actions for followup; expand time by owning tasks and projects, influence or contribute to cross-functional projects; ev. own priorities, scope complete projects
• …and as a strategic advisor and confidant, extra set of hands, proxy on your behalf, and organizer

Stage 2 directive — Orientation towards senior leadership

• Secondary directive (building on and in parallel) is analogous to the first, enabling leadership to operate at a higher level, and helping to formulate and manage the strategic agenda of leadership
• Includes setting the cadence of leadership team interactions, running staff meetings, identifying and furthering high-value topics for pursuit, developing office of leadership as a function company-wide, and looking after teams or initiatives directly
• …and as a facilitator of positive team dynamics and creating environments for productive dialogue

Stage 3 directive — Orientation towards the organization

• The third directive asks, given the aims, how contributions to company-wide strategy and direction can be pursued with a focus on improving organizational design and key business capabilities.
• Includes working to design and implement effective organizational structures, tools and processes, prioritizing targets and influencing or orchestrating investments in the people, process and technology required, as well as critical governance mechanisms
• …and as an interface of leadership overseeing connection points among business units or functions

First 90 Days

• Shadow coverage of principal’s projects, routines, meetings, and work style
• Agenda setting and CoS routines of business, first projects and workflow
• Invest time and establish relations with key leadership as a basis for later collaboration
• Communicate a representative understanding of the role to relevant company stakeholders
• Identify key business areas / leaders and partners for first learnings, deep dives or projects
• Other, based on relevant primary role orientations and principal’s, company’s priorities
• (Later) prioritized exposure to all parts of business through weekly team rotations
• (Later) begin building relationships with board members, other external stakeholders
• (Later) begin a Chief of Staff playbook for the Office of the CEO function, relation to senior leadership, and goals and action items across the organization over the subsequent year

Role Development

Onboarding to the Chief of Staff function

• Before my start date, and through onboarding to the organization and tasks of the principal, additional time will be spent on studying the role and from experienced Chiefs of Staff at similar companies (size, industry, structure)
• Membership to the Chief of Staff Network’s community and participation in the Foundations Track learning course, and with the goal of identifying and engaging with an experienced operator-mentor to maximize my outcomes
• Front-loaded emphasis on attendance to additional learning, networking and community building opportunities relevant for Chiefs of Staff, the company, and or current or future relevant markets etc.

Long term development and role exit

• Chiefs of Staff often move to lead new or existing business units in periods of establishment or transition, or to fill capacity vacuums as they arise
• Chiefs of Staff generally contribute to a 2-3 year period of growth before transitioning internally or becoming CoS/similar at another organization
• The role benefits from weeks to months overlap with next replacements, just as newly established CoS’ benefit from high buy-in onboarding

Talents, Routines & Motivations

Relevant strengths

• Structured, process-oriented project manager, adept at balancing priority, quality, and speed
• Matured EQ, facilitation training and experienced network/relationship builder with senior leadership
• Perseverant generalist and adaptable self-starter talented at operating in ambiguous environments

Working routines

• Preference for fixed routines, dynamic work environments and practiced time management
• Preference for majority in-office, hybrid as appropriate, with periods of remote built-in
• I work hard and play hard, but need to be better at not being “always on” and take rest

Intrinsic motivations

• Life-long entrepreneurial learner with a deeply held need to contribute, support others and grow together
• Goal of making a positive contribution to a struggling world and by way of an impactful, successful career
• I love the ocean (dad studied marine bio) and want to contribute to responsible resource management

External motivations

• Challenging technical, dynamic and interesting work / environments inspire me to work hard and commit
• I am motivated by money but not status, and because I want to have a comfortable life and to support family
• Succeeding in Norway is now an over 13 year journey and I’m still a long way from taking my celebratory lap

Resources

Reports

Articles

• Chief of Staff Leveling Framework
• Chief of Staff: A Critical Role Among High Growth Startups
• Do you want to know about the Chief of Staff Role? (+ addl. links)
• First Round Capital: Why You Need Two Chiefs in the Executive Office
• HBR: The Case for a Chief of Staff