Chief of Staff, Trilogy; Remote

Chief of Staff, Trilogy (Remote) - $200,000/year USD

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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 partnership role designed for someone who grasps how reputation, time, and access function at senior levels—and who can deliver flawless execution without direct supervision.

You will serve as a vital extension of the founder's private office, collaborating closely with the Chief of Staff. Your objective is straightforward yet rigorous: guarantee that every external touchpoint involving the founder—whether email, meeting, media engagement, or public appearance—is deliberate, thoroughly prepared, and managed with sound judgment. The role demands autonomous decision-making, refined instincts, and the assurance to act without continual oversight.

While this position is fully remote, it is not detached. You will be tightly integrated into the founder's daily operations, handling high-priority inbound communications, safeguarding focus, and ensuring that only the most meaningful conversations occur at the optimal moment. If you have previously supported a high-profile CEO, hedge fund principal, or UHNW individual—and understand which engagements create value and which do not—this will resonate.

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

This role is designed to safeguard the founder's most critical resources: time and reputation. If you operate at this caliber with accuracy, discretion, and polish—particularly in a remote capacity—we encourage you to apply.

• Manage the founder's inbox and calendar, applying decisive judgment to triage high-volume external requests.
• Collaborate with the Chief of Staff to synchronize scheduling, priorities, and preparation with overarching strategic goals.
• Compose, refine, and ghostwrite executive communications that convey clarity, authority, and purpose.
• Act as the principal liaison for senior external parties, including CEOs, investors, advisors, and press representatives.
• Guarantee the founder is comprehensively briefed for meetings, interviews, and public engagements, with precise context and accountability for follow-up.

• Awaiting detailed instructions or ongoing approval at every step.
• Functioning as a passive calendar manager without contextual awareness or judgment.
• Escalating every decision without exercising discretion.
• Interpreting "remote" as diminished accountability or reduced standards.
• Working without precision, polish, or dependable follow-through.

Safeguard and enhance the founder's impact by applying independent judgment to control time, access, and external-facing communication.

• 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…