Chief of Staff (Executive Office) and VP of Strategy & Operations

📋 Description

• Chief of Staff to CEO and CBO; lead Strategy & Operations.
• Translate strategy into execution across Flex.
• Hybrid role with on-site 2-3 days/week in NYC HQ.
• Oversee board materials, messaging, and external engagements.
• Own cross-functional, enterprise strategy initiatives end-to-end.
• Build and mentor the S&O team; set standards and priorities.

🎯 Requirements

• 15+ years in management consulting or senior S&O, Biz Ops, or Chief of Staff.
• First-principles problem solver in ambiguous environments.
• Proven team leadership; build and scale high-performing teams.
• Outstanding written and verbal communication; executive presence.
• Demonstrated AI fluency; leverage AI tools to accelerate analysis.
• NYC-based; able to work 3+ days/week at Union Square office.

🎁 Benefits

• Competitive medical, dental, and vision.
• Company equity.
• 401(k) plan with company match.
• Unlimited PTO + 13 company paid holidays.
• Parental leave.
• Flex Cares Program: Non-profit company match + pet adoption coverage.