Chief of Staff


The Chief of Staff manages the daily administration of the executive department, working closely with the CEO and other executives. They focus on making the department, and the company as a whole, more effective, efficient, and reliable. They help ensure that decisions made by senior staff are disseminated and implemented properly across the company, as well as ensuring that crucial feedback and information from the team trigger actions by leadership.

The Chief of Staff must know Cantilever’s established playbook, but also frequently improvise. They will frequently be the one to codify high-level decisions into our handbook. Their key performance indicator is how efficient and effective the executive team are, as reflected in the happiness of the team and the health of the business as a whole. Cantilever believes in transparency, humanity, and empathy, and the Chief of Staff is responsible for helping to ensure those values remain vital to our workflow even as we scale.

The Harvard Business Review wrote that the role involves:

”...serving as an air traffic controller for the leader and the senior team; as an integrator connecting work streams that would otherwise remain siloed; as a communicator linking the leadership team and the broader organization; as an honest broker and truth teller... and as a confidant... Aylward points out that “while a CEO’s other direct reports typically emphasize their own areas, a good CoS can consider the needs of the whole enterprise.”

Overlap with Director of Operations

This is an administrative role and as such we need to carefully define the distinction between the CoS and the director of operations and other administrative positions. To clarify this distinction, we have created an "Executive Department" in which both the CEO and the CoS work. This is a broader umbrella for the tasks and responsibilities that previously fell to the CEO directly or were somewhat inconveniently foisted onto Operations.

Broadly speaking, the Operations department makes choices and determinations that apply to the whole company, such as our software tools, HR policies, benefits, etc. The Executive department participates in these decisions. The Operations department is focused on handling the practical needs of the company today. The Executive department is more generally focused on future planning and growth (recruiting, sales, marketing, networking, etc).

In general, the CoS handles duties that would normally fall to the the CEO, and acts as something of an extension to the CEO’s purview. The CoS is not in the operations department. However, the Operations department works frequently with the CoS in the way it would otherwise work directly with the CEO, and will often take advantage of the CoS’s specific knowledge and skills.

Difference from an EA

Executive Assistant is another potential role we may hire for in the future as a part of the executive department. The CoS shares many responsibilities with an EA, but has more oversight and latitude to make independent decisions. An EA would work primarily just with the specific executive they work for, whereas the CoS works broadly with lots of different parties in the organization. The CoS is expected to make more decisions independently and direct more of the CEO’s activity themselves rather than following the directions of the CEO. The CoS should be thinking of things the CEO isn’t. A promotion track for an outstanding EA would be to become Chief of Staff.

Key Responsibilities

These examples refer to a CEO but the CoS may in the future work with other executives as well.

Executive Coordination

  • Manage the CEO’s schedule. Ensure that schedule conflicts are managed in advance. Make sure that meetings are scheduled in a way that is realistic to the executive’s other commitments. Cover both business and personal commitments and help ensure that the CEO’s work-life balance remains intact.
  • Run meetings that the CEO is involved in so that they can focus on the substance of the discussion. Ensure that all meetings have agendas, and that they start on time. Be the one to ping anyone who does not join exactly on time. Keep meetings timeboxed and efficient. Take notes and distribute them promptly. Translate action items into Basecamp todos for the relevant team members.
  • Arrange local and out-of-town travel for the CEO and other team members. Coordinate complex schedules involving on-the-ground meetings, networking events, 1:1 meetings, and so on. Ensure that travel is planned efficiently to meet the specific needs of each trip. Attend trips which require multiple representatives from the Cantilever side.
  • Arrange, suggest, and facilitate networking and speaking opportunities for the CEO. Keep tabs on local networking events for each executive and schedule appropriate events for them at times that suit their schedule. Arrange travel when appropriate. Join networking events as another representative of Cantilever and in order to provide direct logistical support (such as helping facilitate a smooth live presentation)
  • Assist the CEO in decision-making, acting as an advisor and also a proxy for decisions that can be made independently by the CoS. Interact with the entire company to ensure that they are getting what they need from the CEO and vice versa.
  • Draft communication, including proposals, networking outreach, blog posts, social media posts, and so on. Work with executives to refine and publish this communication. Act as a "first reader" of outbound communication written by the CEO to ensure that it is accurate and thought-through.
  • Monitor the CEO’s inboxes and process requests or questions that can be handled independently.
  • Help the CEO with recruiting research and outreach
  • Perform background research on individuals meeting with the CEO and provide the CEO background information before the meeting. Handle miscellaneous research tasks.
  • Purchase items on behalf of the CEO. Handle returns and shipping.
  • Handle miscellaneous personal tasks for the CEO, such as coordinating doctor’s visits, handling paperwork, helping with personal accounting, etc.

Sales & Marketing

  • Maintain the Cantilever contact database, ensuring that irrelevant inbound leads are pruned regularly and that quality notes and background exist for each person. Identify areas of our network that we are spending too little time with, and coordinate meetings with them and our team.
  • Be the principal recipient of inbound sales communication (live chat, email, etc). Assess the legitimacy of inbound inquiries and reject those not worth our time. Reply to legitimate leads and loop in the appropriate people on the team.
  • Help manage Cantilever’s marketing strategy and tactics, particularly ensuring that our marketing remains in line with the day-to-day happenings at the company.
  • Help find potential Cantilever clients by keeping an eye on the business landscape and understanding the value that Cantilever brings. Draft and/or send communication to prospective clients.
  • Help to draft paperwork for prospective clients

Team Coordination

  • Coordinate and implement initiatives directed by the CEO, such as opening a new office or updating all of our handbook entries to reflect a particular change
  • Help coordinate team events, or external events we sponsor, such as for the Global Fund for Children
  • Help with service and studio management as needed by the Operations team
  • Help reach out to prospective Cantilever team members to invite them to speak with us about work
  • Regularly review tasks previously issued from the Executive department to the team and follow up on any incomplete ones.