Chief of Staff, Ops & Strategy (AI-Driven)

Squarespace; United States; Remote; USD 180,000 - 240,000; Full time

Benefits offered by this job

Medical plans

Life Insurance

Fertility benefits

Headspace

Job summary

United States Digital Space LLC is seeking a Chief of Staff-style operator to serve as the President’s right hand and help run, maintain, and evolve the Product, Engineering & Design operating model and cadence.

The role turns strategy into durable execution, connecting inputs, decisions, and commitments across senior leaders. AI fluency and strong communication are essential as you partner with Product, Engineering, Design, and Finance to accelerate delivery.

Qualifications

• Significant experience in Chief of Staff, Product Operations, Business Operations, Strategy & Operations, or management consulting.
• Proven track record owning an operating model, leadership cadence, or portfolio of cross-functional initiatives, preferably in tech companies.
• Knowledge of the product/software development lifecycle.
• Experience integrating enterprise AI tools into daily workflows to automate tasks, improve synthesis, and accelerate delivery.
• Exceptional written communication with concise, decision-ready narratives.

Responsibilities

• Run the President's operating cadence across staff meetings, reviews, and inputs with clear ownership and decisions.
• Drive decision quality by synthesizing inputs into concise narratives and tracking decisions and owners.
• Improve execution velocity by surfacing risks early and facilitating cross-functional resolution using AI tools.
• Evolve the operating model by applying health measures and codifying changes in cadence and governance.
• Lead high-priority strategic initiatives from framing to follow-through and link to budgets and headcount.
• Represent the President in meetings and maintain transparency through town halls and written follow-ups.
• Serve as a trusted thought partner to the President and senior leadership with independent perspectives.

Skills

Executive ops

Strategic thinking

Communication

Stakeholder influence

Ambiguity tolerance

AI fluency

Cross-functional leadership

Financial acumen

Tools

ChatGPT

Gemini

Claude

Glean

Cursor

Job description

United States Digital Space LLC is seeking a Chief of Staff-style operator to serve as the President’s right hand and help run, maintain, and evolve the Product, Engineering & Design operating model and cadence.

The role turns strategy into durable execution, connecting inputs, decisions, and commitments across senior leaders. AI fluency and strong communication are essential as you partner with Product, Engineering, Design, and Finance to accelerate delivery.