Head of Executive Operations, Trilogy; Remote

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

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 a traditional administrative position. It is a high-stakes executive partnership role designed for someone who understands the mechanics of time, reputation, and access at senior levels—and who can deliver flawlessly without being in the room. You will function as a vital extension of the founder's private office, collaborating closely with the Chief of Staff. Your mission is straightforward yet rigorous: ensure that every external engagement involving the founder—whether email, meeting, interview, or public appearance—is purposeful, thoroughly prepared, and managed with sound judgment.

This role demands autonomous decision-making, sharp instincts, and the ability to act decisively without needing continuous approval. This is a fully remote position, but not a detached one. You will be intricately woven into the founder's daily operations, managing high-priority inbound, safeguarding focus, and ensuring only the most relevant conversations occur at the optimal moment. If you have previously supported a high-profile CEO, hedge fund principal, or ultra-high-net-worth individual—and you understand which engagements create value and which do not—this role will resonate.

If you require physical proximity, detailed instruction at every turn, or frequent validation, it will not. This role exists to safeguard the founder's most critical resources: time and reputation. If you are equipped to operate at this caliber with precision, discretion, and professionalism—particularly from a remote environment—we want to connect with you.

• 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 meeting preparation with overarching strategic goals.
• Draft, refine, and ghostwrite executive communications that convey clarity, credibility, and strategic intent.
• Act as the first point of contact for high-level external stakeholders, including CEOs, investors, advisors, and media representatives.
• Guarantee the founder enters every meeting, interview, and public engagement fully briefed, with comprehensive context and robust follow-through.

• Relying on detailed instructions or awaiting approval for every action.
• Functioning as a passive calendar coordinator devoid of judgment or strategic awareness.
• Escalating every choice to leadership.
• Viewing "remote" as synonymous with reduced accountability or diminished standards.
• Operating without the polish, precision, or consistent follow-through expected at this level.

Safeguard and enhance the founder's productivity by exercising autonomous judgment over time allocation, external access, and outbound communication.

• 8–12+ years of experience supporting senior executives, founders, or ultra-high-net-worth principals.
• Proven ownership of inbox and calendar management for high-profile individuals.
• Demonstrated experience handling executive-level, external-facing communications.
• Outstanding written communication skills—clear, confident, and authoritative.
• Established discretion in confidential, NDA-governed settings.
• Strong capacity for independent judgment and comfort acting decisively without ongoing oversight.
• Based in the U.S. and able to maintain high availability in alignment with senior-executive schedules.

• Background as an Executive Assistant, Executive Business Partner, or senior private office lead supporting a publicly visible CEO.
• Experience in a Chief of Staff, family office, or private investment office capacity.
• Prior work in finance, technology, media, or political environments where reputation and public perception are paramount.

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things:
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