Head of Executive Operations, Trilogy; Remote

Head of Executive Operations, Trilogy (Remote) - $200,000/year USD

Join to apply for the Head of Executive Operations, Trilogy (Remote) - $200,000/year USD role at Crossover

This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

$100.00/hr - $100.00/hr

This is not an administrative position. It is an executive partner role designed for someone who understands how time, access, and reputation function at the senior-most levels—and who can deliver precision outcomes independently, without being present in every conversation.

You will function as an essential extension of the founder's private office, collaborating closely with the Chief of Staff. Your remit is clear and exacting: ensure every external engagement involving the founder—whether email, meeting, interview, or public appearance—is deliberate, thoroughly prepared, and managed with sound judgment. This position demands autonomous decision-making, sharp instincts, and the ability to act without seeking continuous approval.

This is a fully remote position, but not a detached one. You will be closely integrated into the founder's day-to-day operations, managing high-priority inbound activity, safeguarding focus, and ensuring only the most relevant conversations occur at the appropriate moments. If you have previously supported a high-profile CEO, hedge fund manager, or ultra-high-net-worth individual—and you understand which engagements create value and which do not—this role will be immediately recognizable.

If you require physical proximity, detailed instruction, or frequent validation, it will not be a fit.

This role is built to protect the founder's most critical resources: time and reputation. If you are capable of operating at that standard with accuracy, discretion, and professionalism—particularly in a remote capacity—we would like to hear from you.

• Take full ownership of the founder's inbox and calendar, making decisive triage decisions on high-volume external correspondence and requests.
• Collaborate with the Chief of Staff to synchronize scheduling, priorities, and meeting preparation with overarching strategic objectives.
• Draft, refine, and ghostwrite executive-level correspondence that conveys clarity, authority, and strategic intent.
• Act as the principal liaison for senior external parties, including CEOs, investors, advisors, and media representatives.
• Guarantee the founder is comprehensively briefed for meetings, interviews, and public engagements, with full context and reliable follow-through.

• Awaiting detailed instructions or continuous sign-off on every action.
• Functioning as a passive calendar manager without exercising judgment or understanding context.
• Escalating every decision upward without independent resolution.
• Interpreting "remote" as synonymous with reduced accountability or lower performance standards.
• Delivering work without polish, precision, or consistent follow-through.

Safeguard and enhance the founder's effectiveness by applying independent judgment to decisions regarding time allocation, access control, and external communications.

• 8–12+ years of experience supporting senior executives, founders, or ultra-high-net-worth principals.
• Direct responsibility for managing inboxes and calendars of high-profile individuals.
• Demonstrated experience handling external-facing, executive-level communications.
• Outstanding written communication skills—concise, confident, and commanding.
• Proven discretion in sensitive, confidential, and NDA-protected environments.
• Strong capacity for independent judgment and comfort acting decisively without ongoing supervision.
• U.S.
  
  -based and capable of maintaining high availability consistent with senior-executive schedules.

• Background as an Executive Assistant, Executive Business Partner, or private office leader supporting a publicly visible CEO.
• Chief of Staff, family office, or private investment office experience.
• Professional exposure to finance, technology, media, or…