Chief of Staff — Strategy, Operations & Growth

OuterSignal; United States; Remote; USD 150,000 - 230,000; Full time

Benefits offered by this job

Massive equity

Proven product impact

Urgent, high-impact team

Job summary

OuterSignal is hiring a Chief of Staff to drive strategy into execution in a fast-growing e-commerce tech company. You will partner with the VP of Operations and the CEO to own planning, cadence, and cross-functional initiatives.

You’ll build systems, run OKRs, manage investor and partner relationships, and enable rapid hiring as the org scales. This is a hands-on, ownership-driven role at an early-stage company that values AI-enabled decision-making.

Qualifications

• 3–7+ years in a Chief of Staff, startup operations, business operations, or founder’s-office role at a high-growth company.
• Hands-on operator, not a consultant.
• Strong business and financial fluency.
• AI-native: you reach for AI tools to move faster by default.
• Organized and systems-minded with crisp written communication.

Responsibilities

• Be the right hand to the VP of Operations and turn strategy into execution.
• Act as a trusted thought partner to the VP of Operations, CEO, and executive team.
• Protect executive focus and surface bottlenecks early.
• Own company planning: OKRs, operating plan, KPIs and dashboards.
• Partner with finance to align targets with the operating plan.
• Run the operating cadence: exec meetings, standups, decisions.
• Drive cross-functional initiatives, including integration of acquisitions.
• Be a trusted contact for investors, partners, and vendors.
• Lead SOC 2 readiness and other compliance initiatives.
• Power rapid hiring and sharpen recruiting processes.
• Lead special projects including AI adoption.

Skills

Chief of Staff experience

Startup operations

Financial fluency

AI adoption

Systems thinking

Written communication

Ownership mindset

Tools

AI tools

Job description

OuterSignal is hiring a Chief of Staff to drive strategy into execution in a fast-growing e-commerce tech company. You will partner with the VP of Operations and the CEO to own planning, cadence, and cross-functional initiatives.

You’ll build systems, run OKRs, manage investor and partner relationships, and enable rapid hiring as the org scales. This is a hands-on, ownership-driven role at an early-stage company that values AI-enabled decision-making.