Mission of the Chief of Staff to the CEO

The Chief of Staff and his or her team will exercise manager-level “business generalist” capabilities to deliver strategic and tactical execution against miscellaneous business needs that arise between or across the responsibilities of Trellis’ functionally-organized departments.

Unlike an Executive Assistant, who will tend toward well-defined, repeatable tasks requiring minimal strategic perspective or off-hour attention, the Chief of Staff will shadow and support the CEO on projects and activities harboring considerable complexity, business-criticality, and/or strategic pertinence.

This may include:

  • Projects that involve many functions
    • E.g. stewarding OKRs, preparing exec offsite, board meeting, fundraising slides
  • Projects that are important but are under resourced
    • E.g. designing interviews for a new exec hire; sourcing for our advisory board
  • Projects that are too early, broad, or nebulous to allocate to a functional owner
    • E.g. exploration of M&A opportunities and “greenfield” business ideas
  • Projects that are important to the CEO
    • E.g. designing a process for publicly highlighting or rewarding team members who invest a lot of time into interviewing candidates for other teams


  • This role would be expected to last 12-24 months, after which the Chief of Staff would hire a backfill and take another role inside or outside the company – most likely in a leadership capacity.

Key inspirations/references:

Outcomes from the Chief of Staff to the CEO

Coordination of processes and projects that involve multiple departmental functions

30 Days: Consolidating existing company and department OKRs

90 Days: Organizing an all-staff offsite; coordinating new OKRs; standardizing ways to ensure departments move institutional knowledge into the wiki

365 Days: Re-designing product-sales interface/KPIs for next level of scale

Completion of complex tactical projects requiring senior-level judgement

30 Days: Accurately completing an application to renew corporate insurance

90 Days: Selecting interview questions for a new executive hire (e.g. CFO)

365 Days: Drafting board updates; preparing CEO’s own performance review

Execution of broad, strategic projects riddled with ambiguity

30 Days: Identifying an “insurance luminary” to add to our advisory board

90 Days: Updating company values; proposing headcount allocations

365 Days: Quantifying business opportunity and ROI from expanding to Canada


Detail-oriented – This person will work with a lot of numbers and details of critical importance. Inaccuracies could cost the business millions.

Independent and self-managing – Learns and adapts osmotically, without direct guidance. Independently identifies and self-directs to highest priorities among many. Accurately predicts required effort, time, and expense, especially for own projects. Ultimately delivers accurate timelines by reconciling with own capacity.

Concise, precise, persuasive communicator – Concise because this person will interface heavily with expensive people. Precise because he or she will touch a lot of critical subjects with no room for error. Persuasive because this person will need to use logical and other thinking to motivate a diverse organization toward aligned action.

High-throughput, fast-paced context switcher – This person will have a lot to do. All at once.

Self-motivated – This job will be exceptionally challenging, busy, and often short-term unrewarding. We need someone who brings 110% no matter what, and who is eager to learn and to build the experience and exposure that this position enjoys.

Personable – This person will work with a lot of different personalities and will need to be liked in order to establish alignment among them.

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