Head of Executive Operations, Trilogy; Remote

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

Join Crossover as the Head of Executive Operations for Trilogy, working remotely.

$100.00/hr - $100.00/hr (equivalent to $200,000/year).

• 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 political environments where reputation and public perception are critical.

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for relentlessly seeking top talent, innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer‑facing designs, while 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 per hour, which equates to $200,000 USD per year assuming 40 hours per week and 50 weeks per year. The payment period is weekly.