Chief of Staff to the CEO

Chief of Staff to the CEO

Be at the Forefront of the Agentic AI Revolution

At Skan AI, we are pioneering the context engine for human and agentic execution, bringing context from enterprise operators, systems, and processes to power how the world's largest organizations execute their most complex, mission-critical work.

Why Skan AI

We're in hyper-growth mode at exactly the right moment in history. As enterprises race to adopt agentic AI, we're uniquely positioned to deliver the clear signal they desperately need: a platform that trains and grounds AI Agents in trillions of real execution signals, enabling reliable, compliant automation of their most complex processes.

Backed by Dell Technologies Capital and other leading investors, we're the only company that can bridge the gap between AI's promise and enterprise reality, making us perfectly positioned to define the agentic era for modern enterprises.

Our diverse, collaborative team of 250 innovators is solving category-defining challenges at the intersection of AI, process intelligence, and enterprise work. Diverse perspectives fuel breakthrough thinking, cross-functional collaboration is the norm, and our work directly transforms how Fortune 500 companies operate. We are shaping the future of work itself.

About the Role

We’re looking for a Chief of Staff to the CEO — a high-agency operator who can act as a true force multiplier to the CEO across strategy, operations, and growth. This is not a traditional program management role. You’ll be the person the CEO turns to when something important, ambiguous, and cross-functional needs to get done — fast and well.

You’ll work across every dimension of the business: shaping strategic priorities, driving operational rigor, supporting GTM efforts, preparing for board and investor engagements, and ensuring the leadership team is aligned and executing. The right person will have the intellectual horsepower to go deep on complex problems and the pragmatism to drive outcomes in a fast-moving startup environment.

This role is ideal for someone 3–5 years out of a top-tier management consulting firm (McKinsey, Bain, BCG) or with equivalent experience in high-performance operating environments, who is ready to move closer to the action and own real outcomes.

What You’ll Do

Strategic Planning & Executive Alignment

• Partner with the CEO to define and pressure-test strategic priorities, translating them into concrete plans with clear owners and milestones
• Prepare materials and analysis for board meetings, investor updates, and executive offsites
• Serve as a sounding board and thought partner to the CEO on key decisions

Operational Execution & Scaling

• Drive cross-functional initiatives that don’t have a natural owner — the projects that fall between the cracks but matter most
• Build and maintain operating cadences (leadership meetings, QBRs, planning cycles) that keep the company focused and accountable
• Identify bottlenecks and inefficiencies across the organization and work with functional leaders to resolve them

GTM & Revenue Support

• Support strategic sales pursuits, partnerships, and customer engagements alongside the CEO and go-to-market team
• Conduct market and competitive analysis to inform positioning, pricing, and expansion decisions
• Help structure and refine the company’s narrative for customers, investors, and talent

Special Projects

• Lead high-priority initiatives end-to-end — from scoping and analysis to execution and communication
• Step into operational gaps as needed, acting as an extension of the CEO across the organization

Who You Are

• 3–5 years of management consulting experience, ideally with McKinsey, Bain, or Boston Consulting Group (BCG). Candidates with comparable Chief of Staff experience in a complex, highly matrixed environment and a strong academic background will also be considered.
• Exceptional problem solver — you can break down ambiguous, complex problems and drive toward clear answers
• High agency — you don’t wait for instructions; you identify what needs to happen and make it happen
• Strong communicator — you write crisply, present clearly, and can tailor your message for a board room or a Slack thread
• Comfortable with ambiguity — you thrive in fast-moving environments where priorities shift and you need to figure things out on the fly
• Analytically sharp — you’re fluent with data and can build models, analyze markets, and structure business cases
• Low ego, high horsepower — you’re willing to do whatever it takes, from building a board deck to coordinating a customer escalation
• Genuine interest in AI and enterprise technology — you don’t need to be technical, but you should be curious and able to learn quickly

Nice to Have

• Experience at or exposure to enterprise SaaS, AI/ML, or process intelligence companies
• Prior experience in a startup or high-growth environment
• Familiarity with financial modeling, fundraising, or investor relation

Why Join Skan AI?

• Be part of a category-creating company building the full agentic lifecycle.
• Own some of the most strategic BFSI enterprise relationships in the market, with a direct line to the C-suite at the world's largest financial institutions.
• Join a passionate, global team united by curiosity, integrity, and impact.
• In-office and remote work mix with global exposure.
• Competitive compensation and equity opportunities.

Benefits

• 100% coverage of Health Care Plan (Medical, Dental & Vision)
• Retirement Plan (401k, IRA)
• Life Insurance (Basic, Voluntary & AD&D)
• Unlimited Paid Time Off (Vacation, Sick & Public Holidays)
• Short Term & Long-Term Disability
• Work From Home
• Stock Option Plan

Ready to help shape the future of enterprise AI? Click Apply to get started—our application is designed to be as fast as the company itself.

Skan AI is an equal opportunity employer committed to building a diverse, inclusive, and respectful workplace around the world. We do not discriminate based on race, color, religion or belief, sex (including pregnancy, sexual orientation, gender identity, or gender expression), national origin, ancestry, age, disability, medical condition, genetic information, marital or family status, military or veteran status, or any other characteristic protected by applicable laws in the locations where we operate.

We welcome people from all backgrounds and provide reasonable accommodations throughout the hiring process.

www.skan.ai