Chief of Staff

Description

• Serve as right-hand to CEO, managing execution of the CEO’s top priorities, ensuring alignment, progress, and accountability
• Act as a thought partner and sounding board to the CEO and broader executive leadership team
• Drive key cross-functional initiatives across all departments: sales, marketing, engineering, product, business operations, finance, professional services, and support
• Identify and drive the adoption of AI tools and workflows to improve operational efficiency, accelerate execution, and help scale the business
• Identify gaps in existing systems or processes, and create and implement solutions to fill those gaps
• Support planning cycles (monthly, quarterly, annual), including goal setting, business reviews, and strategy development
• Prepare briefing materials, presentations, and follow-ups for internal and external meetings
• Develop internal dashboards, operating rhythms, and reporting tools to support decision-making, including the Flexi Scorecard – a snapshot of the most important metrics by which we hold ourselves accountable
• Step into gaps across the organization and thrive in high-need areas, delivering value wherever plugged in

Requirements

• 2+ years of experience in consulting, investing, strategy, operations, or similar analytical roles
• Demonstrated experience supporting or working alongside senior executives
• Strong project management, organizational, and communication skills, with high attention to detail
• Ability to synthesize complex issues, develop structured recommendations, and drive execution
• Comfort with financial statements, metrics, and Excel modeling
• Experience in enterprise software, B2B SaaS, or technology-enabled services is a plus

Benefits

• Paid holidays and paid time off
• 401(k) Plan with company participation
• Health and dental insurance
• Life and disability insurance
• Vision discount plan

Salary: $95k - $115k / year