Gross Labs is a modern family enterprise platform founded by Nick Gross, dedicated to building, acquiring, and investing in culture-driven businesses across sports, media/entertainment, education, real estate development, hospitality, and consumer ventures. The platform operates a diverse portfolio of operating companies, investment projects, development initiatives, and a philanthropic foundation. As Head of Operations, you will play a pivotal role in shaping and scaling the operational infrastructure of a multi-entity holding company. You will work closely with the founder/CEO and senior leadership to drive strategic initiatives, standardize processes, and ensure seamless execution across business units. This is a unique opportunity to impact a dynamic, founder-led enterprise with broad reach and ambitious growth plans. Key responsibilities include: • Build and manage the enterprise operating cadence across operating companies, investments, development initiatives, and foundation efforts • Create systems for visibility, reporting, and decision-making across business units • Oversee enterprise KPI dashboards and executive performance tracking • Drive cross-functional strategic initiatives from concept through implementation • Align operating-company priorities with the broader investment and growth strategy • Lead special projects such as new venture launches, partnerships, acquisitions, and expansion • Coordinate across operating company leaders, investment/development partners, and internal stakeholders • Ensure efficient communication, track deliverables, and hold teams accountable to timelines and goals • Coordinate milestone tracking for large-scale development projects, including Oklahoma City initiatives • Partner directly with the founder/CEO to prioritize focus and prepare briefing materials, dashboards, and decision frameworks • Build scalable operational infrastructure, standardizing reporting, planning cycles, and governance rhythms • Improve organizational efficiency through process design and automation Requirements Required Qualifications: • Master’s degree • Experience managing multiple priorities across multiple business lines • Experience building operational systems for visibility, reporting, and decision-making across teams or business units • Experience leading cross-functional strategic initiatives from concept through implementation • Demonstrated financial, operational, and project management fluency in an operations leadership role • Proficiency with Google Workspace tools (Google Sheets, Google Docs, Google Calendar) • Proficiency with ClickUp or Notion • Experience partnering directly with a founder/CEO (or equivalent executive) to prepare briefing materials, dashboards, and decision frameworks Preferred Qualifications: • Experience operating in a multi-entity environment such as a holding company, family office, venture platform, diversified operating group, or complex founder-led enterprise • Experience with venture investing and/or portfolio operations • Experience with real estate development and/or mixed-use project coordination Benefits • Comprehensive health insurance coverage (medical, dental, vision) • 401(k) retirement plan with company match • Generous paid time off and holidays • Flexible hybrid work environment based in Newport Beach, CA • Professional development opportunities and executive coaching • Opportunity to work directly with founder/CEO and senior leadership • Team events and a collaborative, culture-driven workplace