Chief of Staff - AI-Driven Strategy & Execution

Pindrop; United States; Remote; USD 230,000 - 286,000; Full time

Benefits offered by this job

RSUs

Remote-first environment

Unlimited PTO

Health benefits

HSA contributions

Learning stipend

Job summary

Pindrop is seeking an experienced Chief of Staff to partner with the CEO and ELT, accelerating decisions and execution during a period of rapid growth. The role focuses on strategic operations, information flow, and using AI to enhance output and organizational planning.

You will work across teams to shape the operating model, governance, and leadership rhythm. You’ll be expected to synthesize complex topics into clear, executive-ready narratives, manage critical programs, and drive

Qualifications

• 3+ years at top-tier management consulting, investment banking, or VC/PE
• 3+ years at a hyper-growth tech company
• Hands-on use of AI tools daily in work
• Strong problem identification and executive presence
• Highly organized with data-driven decision making
• Entrepreneurial mindset for rapid growth in a scaling company

Responsibilities

• Plan rhythm of business: OKR reviews, ELT syncs, and board prep
• Identify internal issues, market trends, and key data for planning
• Drive cross-functional alignment and resolve stalled decisions
• Draft notes, agendas, and action items for leadership meetings
• Build dashboards, models, and research to accelerate decisions
• Lead special projects: market scouting, org design, or partnerships
• Prepare materials for all-hands, board meetings, and investor updates

Skills

Executive-level collaboration

AI fluency in daily workflow

Strategic planning & OKR process

Cross-functional leadership

Data-driven decision making

Problem solving under ambiguity

Executive communication

Dashboards & reporting

Tools

AI tools (Claude/ChatGPT)

Job description

Pindrop is seeking an experienced Chief of Staff to partner with the CEO and ELT, accelerating decisions and execution during a period of rapid growth. The role focuses on strategic operations, information flow, and using AI to enhance output and organizational planning.

You will work across teams to shape the operating model, governance, and leadership rhythm. You’ll be expected to synthesize complex topics into clear, executive-ready narratives, manage critical programs, and drive