The Client

Our client is a founder‑led, high‑growth organization entering a critical phase of scale. The CEO is a visionary, high‑output operator seeking a trusted, senior partner to help increase leverage, clarity, and effectiveness at the highest level of the business. This is a discreet, fast‑moving environment where judgment, timing, and trust are paramount.

The Role

This is a rare, senior Operations Executive role working directly alongside the CEO. It is not a traditional Executive Assistant or Chief of Staff position. There are no direct reports and no responsibility for administrative or logistical execution, which is handled separately.

The role sits at the center of the CEO’s day‑to‑day world. You will listen closely, observe patterns, synthesize information, and help ensure focus remains where the CEO creates the most value. Impact comes from judgment, synthesis, discretion, and the ability to operate fluidly in ambiguity.

Key Responsibilities Include:

Sitting alongside the CEO in meetings and calls to actively listen and synthesize discussions
Identifying priorities and proactively redirecting focus
Filtering information, ideas, and inputs to surface what truly matters
Tracking key threads to ensure critical issues do not fall through the cracks
Providing real‑time, thoughtful feedback to sharpen decision‑making
Bringing structure and clarity to complex, fast‑moving situations
Supporting ad hoc strategic and personal business initiatives as needed

The Candidate

The ideal candidate is wired to operate in ambiguity and thrives as a long‑term partner to a demanding, creative, fast‑thinking founder.

This role is likely a fit if you:

Have partnered closely with a high‑output, demanding executive
Add value instinctively without needing direction
Are systems‑oriented, intellectually curious, and reflective
Are highly attuned to people, communication, and interpersonal dynamics
Exercise excellent judgment and discretion naturally
Prefer influence and leverage over formal authority
Are seeking a long‑term partnership, not a stepping‑stone role

This role is not a fit if you:

Are primarily task‑ or execution‑oriented
Need clear structure or instruction to be effective
Are seeking a short‑term or résumé‑driven position
Prefer formal hierarchy or direct ownership of execution
Find ambiguity uncomfortable rather than energizing

Compensation, Benefits & Work Schedule

Base salary: $250,000–$300,000, dependent on experience
Discretionary year‑end bonus
Long‑term equity participation
Comprehensive health benefits and 401(k)
Meaningful wellness benefits
Unlimited PTO

Location & Travel

This is a fully in‑person role, split between two primary locations within the continental U.S. Frequent travel and seasonal relocation are required. Flexibility is essential.

Joss Search is proud to be an Equal Opportunity employer, passionately supporting and promoting equality, diversity and inclusion. We are committed to building an inclusive culture, respecting our individual differences and bringing our community together

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