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

Ready to be the strategic force multiplier behind exceptional leadership? As Head of Executive Operations, you'll transcend traditional EA roles to become the architect of executive excellence. Picture yourself as the mastermind who transforms raw ideas into boardroom brilliance, shields valuable time like a fortress, and turns complex challenges into seamless solutions.

At Trilogy, where excellence is the baseline, you'll join a company that celebrates builders and visionaries. This isn't about managing a calendar—it's about engineering systems that amplify executive impact. You'll be the invisible hand that transforms chaos into clarity, the strategic partner who anticipates needs before they arise, and the guardian of executive bandwidth.

If you're the person who's known for making the impossible look effortless, who thrives on turning executive vision into reality, and who has a track record of creating order from complexity, we need to talk. This role is your opportunity to elevate executive effectiveness to an art form.

What You Will Be Doing

• Orchestrate the executive ecosystem: Transform a high-stakes inbox, calendar, and travel schedule into a masterpiece of efficiency and precision.
• Alchemize ideas into impact: Convert stream-of-consciousness thoughts and voice memos into compelling, actionable communications that command attention.
• Architect operational excellence: Create and maintain sophisticated systems that eliminate friction and maximize executive effectiveness.
• Spearhead mission-critical initiatives: Drive complex personal and professional projects from concept to flawless execution.
• Bridge relationships masterfully: Serve as the diplomatic powerhouse connecting internal leadership, investors, advisors, and family office partners.
  
  

What You Won’t Be Doing

• Playing it safe: This role demands bold decision-making and proactive leadership, not passive task-taking.
• Sharing the wheel: You're the captain of this ship, not part of a rotating crew of assistants.
• Navigating unnecessary layers: Enjoy direct access and clear lines of communication with your executive.
• Wrestling red tape: Experience the freedom to execute without bureaucratic constraints.
• Inheriting broken processes: You'll be empowered to build and optimize systems from the ground up.
  
  

Head Of Executive Operations Key Responsibilities

Serve as the executive's strategic partner in maximizing impact by masterfully orchestrating systems, communications, and mission-critical initiatives across both professional and personal spheres.

Basic Requirements

• Proven track record of 8-12+ years elevating executive effectiveness in senior support roles (EA, EBP, CoS) or high-end client services
• Superior communication abilities: Craft impeccable, compelling content across all professional formats
• Demonstrated excellence in managing comprehensive executive workflows, both business and personal
• Advanced command of contemporary productivity platforms (Google Workspace, Shortwave, Notion, Workflowy)
• Unimpeachable discretion and professional poise; experienced in confidential information management
• Must be Austin-based or ready to relocate; in-person presence essential
• Authorization to work in the United States required (no visa sponsorship available)
  
  

Nice-to-have Requirements

• Direct experience within private office or family office environments
• Background in managing high-end events, property management, or premium service providers
• Strong financial acumen: Experience with budget management and financial documentation
• Excellence in research methodology and rapid synthesis of complex information into polished deliverables
  
  

About Trilogy

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.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

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 www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5659-US-RoundRoc-HeadofExecutiv