Crossover
Head of Executive Operations, Trilogy (Remote) - $200,000/year USD
Crossover, Tampa, Florida, us, 33646
Head of Executive Operations, Trilogy (Remote) – $200,000 per year
This full‑time, independent contractor position is based in the U.S. and requires close integration with the founder’s private office while remaining remote. The role is salaried at $200,000 per year (equivalent to $100 per hour) and involves a 40‑hour work week with weekly payment.
Base Pay Range $100 per hour
Role Overview Act as an executive partner and essential extension of the founder’s private office, working closely with the Chief of Staff to manage schedules, inbox, and external engagements. The position demands autonomous decision‑making, discretion, and the ability to protect the founder’s time and reputation.
Responsibilities
Take full ownership of the founder’s inbox and calendar, triaging high‑volume external correspondence and requests.
Collaborate with the Chief of Staff to synchronize scheduling, priorities, and meeting preparation with strategic objectives.
Draft, refine, and ghostwrite executive‑level correspondence that conveys clarity, authority, and intent.
Serve as the principal liaison for senior external parties including CEOs, investors, advisors, and media representatives.
Ensure the founder is comprehensively briefed for all meetings, interviews, and public engagements, providing full context and follow‑through.
What You’ll Not Be Doing
Awaiting detailed instructions or continuous sign‑off for every action.
Functioning as a passive calendar manager without exercising judgment.
Escalating every decision upward without independent resolution.
Interpreting “remote” as lower accountability or performance standards.
Delivering work lacking polish, precision, or consistency.
Key Responsibilities Safeguard and enhance the founder’s effectiveness through independent judgment on 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 with executive‑level communications.
Outstanding written communication skills—concise, confident, commanding.
Proven discretion in sensitive, confidential, and NDA‑protected environments.
Strong capacity for independent judgment and decisive action without supervision.
U.S.-based with availability aligned to senior‑executive schedules.
Nice‑to‑have Requirements
Background as an Executive Assistant, Executive Business Partner, or private office leader for 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 is critical.
About Trilogy Trilogy has run a business‑platform for three decades, focusing on talent acquisition, technology innovation, and business incubation. It offers a culture of simple customer‑facing designs and growth opportunities for its employees.
Working with Us The role is immediate and requires signing an independent contractor agreement as a Contractor of Record with Crossover. Payment is weekly. For more details, see the FAQ at
Crossover Help & FAQs .
#J-18808-Ljbffr
Base Pay Range $100 per hour
Role Overview Act as an executive partner and essential extension of the founder’s private office, working closely with the Chief of Staff to manage schedules, inbox, and external engagements. The position demands autonomous decision‑making, discretion, and the ability to protect the founder’s time and reputation.
Responsibilities
Take full ownership of the founder’s inbox and calendar, triaging high‑volume external correspondence and requests.
Collaborate with the Chief of Staff to synchronize scheduling, priorities, and meeting preparation with strategic objectives.
Draft, refine, and ghostwrite executive‑level correspondence that conveys clarity, authority, and intent.
Serve as the principal liaison for senior external parties including CEOs, investors, advisors, and media representatives.
Ensure the founder is comprehensively briefed for all meetings, interviews, and public engagements, providing full context and follow‑through.
What You’ll Not Be Doing
Awaiting detailed instructions or continuous sign‑off for every action.
Functioning as a passive calendar manager without exercising judgment.
Escalating every decision upward without independent resolution.
Interpreting “remote” as lower accountability or performance standards.
Delivering work lacking polish, precision, or consistency.
Key Responsibilities Safeguard and enhance the founder’s effectiveness through independent judgment on 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 with executive‑level communications.
Outstanding written communication skills—concise, confident, commanding.
Proven discretion in sensitive, confidential, and NDA‑protected environments.
Strong capacity for independent judgment and decisive action without supervision.
U.S.-based with availability aligned to senior‑executive schedules.
Nice‑to‑have Requirements
Background as an Executive Assistant, Executive Business Partner, or private office leader for 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 is critical.
About Trilogy Trilogy has run a business‑platform for three decades, focusing on talent acquisition, technology innovation, and business incubation. It offers a culture of simple customer‑facing designs and growth opportunities for its employees.
Working with Us The role is immediate and requires signing an independent contractor agreement as a Contractor of Record with Crossover. Payment is weekly. For more details, see the FAQ at
Crossover Help & FAQs .
#J-18808-Ljbffr