Chief of Staff to CEO — Strategy & Execution (Remote)

Ladders; United States; Remote; USD 241,000 - 331,000; Full time

Benefits offered by this job

Health insurance

Vision insurance

Dental insurance

Mental health benefits

RSUs

10% bonus target

Job summary

Ladders is seeking a Chief of Staff to support the CEO and executive team in translating strategy into disciplined execution. This remote role shapes operating cadence, decision-making, and executive communications to keep priorities, metrics, and follow-through aligned.

The ideal candidate brings 15+ years in strategy/operations, strong analytics, and proven cross-functional leadership to drive alignment and impact across a fast-moving technology environment.

Qualifications

• 15+ years of experience in senior strategy, operations, or executive advisory roles.
• Proven track record of influencing executive leaders and driving organizational alignment.
• Exceptional written and verbal communication skills.
• Strong analytical skills with experience in SaaS metrics and executive data.
• Ability to manage multiple high-impact projects with effective prioritization.
• High degree of discretion, integrity, and emotional intelligence.

Responsibilities

• Partner with the CEO to drive strategic initiatives from conception to execution.
• Shape operating rhythm, including OKRs and planning processes.
• Design frameworks for executive decision-making and planning cycles.
• Lead preparation of executive materials with clear alignment to strategy.
• Collaborate on executive dashboards with actionable and accurate metrics.
• Analyze data to inform strategic decisions and provide clear recommendations.
• Design agendas for executive meetings and capture key decisions for follow‑through.

Skills

Strategic thinking

Operations leadership

Executive advisory

Data analysis

Cross-functional collaboration

Discretion and integrity

Job description

Ladders is seeking a Chief of Staff to support the CEO and executive team in translating strategy into disciplined execution. This remote role shapes operating cadence, decision-making, and executive communications to keep priorities, metrics, and follow-through aligned.

The ideal candidate brings 15+ years in strategy/operations, strong analytics, and proven cross-functional leadership to drive alignment and impact across a fast-moving technology environment.