Deputy Chief of Staff - Strategic Execution

Deputy Chief of Staff - Strategic Execution

Company: Highlife MGMT LLC

Role Summary

Highlife MGMT is an impact-driven, founder-led conglomerate headquartered in Las Vegas with strong roots in Los Angeles. The organization serves as the strategic management and venture architecture platform for a growing portfolio of businesses, investments, partnerships, and social-impact initiatives.

The Deputy Chief of Staff – Strategic Execution will serve as the Founder's senior partner across multiple ventures. This is not an Executive Assistant or traditional administrative role. The successful candidate must be capable of working directly alongside the Founder, bringing strong judgment, organizing complex priorities, challenging ideas intelligently, and converting high-level decisions into disciplined execution.

Key Responsibilities

• Serve as a strategic thought partner and execution counterpart to the Founder.
• Analyze opportunities, risks, proposals, and major decisions.
• Prepare executives, briefings, recommendations, and decision frameworks.
• Organize and prioritize high-value matters requiring the Founder's attention.
• Monitor execution, identify bottlenecks, and enforce accountability.
• Handle complex and sensitive matters requiring maturity and discretion.

Requirements/Qualifications

• Minimum years of experience in Chief of staff, corporate strategy, management consulting, corporate development, investment, executive operations, or senior leadership roles.
• Proven experience working directly with a Founder, Chairman, CEO, or high-level entrepreneur.
• Exposure to U.S. businesses, transactions, investments, partnerships, or multi-venture environments.
• Ability to manage complex initiatives and execute independent business judgment.
• Exceptional verbal and written communication.
• Strong executive presence, discretion, organization, and follow-through.
• Ability to work independently in a fast-moving environment.
• Mandatory availability during stated Pacific Time working hours.

Ideal Candidate

The ideal candidate is commercially intelligent, emotionally stable, highly discreet, and comfortable operating without constant direction. This person understands the difference between supporting a leader and merely assisting one, and has the maturity to operate as a trusted extension of the Founder's judgment, priorities, and authority.

Compensation

A competitive compensation package will be offered, commensurate with experience and qualifications.