Private Office Director, Trilogy; Remote

Private Office Director, Trilogy (Remote) - $200,000/year USD

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$100.00/hr - $100.00/hr

This is not a support role in the traditional sense. It is a strategic executive partnership designed for someone who grasps how time, influence, and visibility function at senior leadership levels—and who can deliver exceptional results without needing direct supervision.

You will function as an essential arm of the founder's private office, collaborating closely with the Chief of Staff. Your mission is straightforward yet exacting: guarantee that every external touchpoint involving the founder—correspondence, engagements, interviews, or public appearances—is purposeful, meticulously prepared, and executed with sound judgment. This position demands autonomous decision‑making, sharp instincts, and the assurance to take action without continual oversight.

This is a fully remote position, but not a detached one. You will be tightly integrated into the founder's day‑to‑day operations, handling high‑priority inbound communications, safeguarding focus, and ensuring only the most relevant exchanges occur at the appropriate moments. If you have previously supported a high‑profile CEO, hedge fund principal, or ultra‑high‑net‑worth individual—and you understand which engagements drive impact and which do not—this role will resonate.

If you require physical proximity, detailed instruction, or continuous affirmation, it will not.

This position exists to safeguard the founder's most critical resources: time and reputation. If you are equipped to operate at this level with accuracy, confidentiality, and professionalism—particularly in a remote capacity—we are interested in speaking with you.

• Take full ownership of the founder's inbox and calendar, filtering high‑volume external communications with authoritative judgment.
• Collaborate with the Chief of Staff to synchronize scheduling, priorities, and strategic preparation.
• Compose, refine, and ghost‑write executive communications that convey clarity, command, and purpose.
• Act as the central liaison for senior external parties, including CEOs, investors, advisors, and members of the press.
• Guarantee the founder enters every meeting, interview, and public engagement fully briefed, with comprehensive context and accountability for follow‑up.

• Awaiting detailed instructions or regular sign‑off for routine actions.
• Functioning as a reactive scheduler without strategic context or discretion.
• Escalating every choice to senior leadership.
• Interpreting "remote work" as a license for reduced rigor or responsiveness.
• Delivering work that lacks precision, professionalism, or closure.

Safeguard and enhance the founder's impact by applying independent judgment to time allocation, external access, and high‑level correspondence.

• 8–12+ years of experience supporting senior executives, founders, or UHNW principals.
• Direct ownership of inboxes and calendars for high‑profile individuals.
• Proven experience managing external‑facing, executive‑level communications.
• Exceptional written communication—concise, confident, and authoritative.
• Demonstrated discretion in sensitive, NDA‑bound environments.
• Strong independent judgment and comfort making decisions without constant oversight.
• U.S.
  
  -based and able to operate with high availability aligned to senior‑executive rhythms.

• Experience as an Executive Assistant, Executive Business Partner, or private office lead to a publicly visible CEO.
• Chief of Staff, family office, or private investment office background.
• Experience in finance, tech, media, or politics where reputation and optics matter.

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.

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  for more details on this topic.