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

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.

What You Will Be Doing

• 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.
  
  

What You Won’t Be Doing

• 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.
  
  

Head Of Executive Operations Key Responsibilities

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

Basic Requirements

• 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.
  
  

Nice-to-have Requirements

• 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 political environments where reputation and public perception are critical.
  
  

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5659-US-Elizabet-HeadofExecutiv