The Optimist's Operating System
Chief Optimist
Reports to: Chief Executive
Location: Anywhere the future is being built
Salary: £120,000 to £180,000 plus equity
Nobody has written this job description yet. Here it is.
The role
The Chief Optimist is the executive responsible for the organisation's orientation toward the future. Not its communications. Not its culture programme. Its actual operating posture: whether the leadership team believes what is possible, whether that belief is shared, and whether it is translating into the decisions that get made on Tuesday mornings.
This is not a motivational role. It is a strategic one.
What you will do
- Map the leadership team's belief alignment using the OOS Diagnostic and identify the specific points of divergence
- Run quarterly Belief Audits that surface where the organisation's operating assumptions have drifted from its stated values
- Build and maintain a signal-filtering system for the leadership team: what to read, what to ignore, what to investigate
- Facilitate the conversations that strategy consultants don't have time for and HR consultants aren't equipped to have
- Turn the organisation's wins into compound confidence, not noise
- Represent the organisation at external events in a way that attracts optimistic collaborators, partners and talent
- Advise the CEO on which beliefs are being tested by current conditions and how to hold them publicly
What we are looking for
- A track record of building things under uncertainty, not just advising people who do
- The ability to facilitate a room of 12 senior executives without slides, and leave them with something they didn't have before
- Genuine future literacy: you can explain, in plain language, what AI is changing and what it isn't
- The patience to move slowly through contested beliefs and the confidence to name what you see
- Comfort being the person in the room who believes the most -- and the rigour to back it up
What this is not
- A Chief People Officer role renamed
- A Chief Happiness Officer
- A keynote speaker on retainer
- An executive coach repackaged
Who the best candidates will have been
A strategist who got bored of decks. A founder who discovered they were better at orienting teams than running them. A consultant who kept noticing that the real problem wasn't the strategy -- it was what the leadership team believed about their own situation.
This role does not exist at most organisations yet. If you think yours needs one, start by booking a Belief Audit. The diagnostic is where every Chief Optimist engagement begins.
Book a Belief Audit