Executive Assistant - AI Labs

Leadout Capital; New York (NY); On-site; USD 90,000 - 130,000; Full time

Job summary

AI Labs is seeking an exceptional Executive Assistant to support a senior leader overseeing M&A, investing, product, engineering, operations, and portfolio initiatives. The role blends executive partnership with curiosity for AI, using AI and automation to create context, continuity, and leverage across a rapidly changing portfolio.

The environment is fast-moving, highly interconnected, and confidential. You will anticipate priorities, protect sensitive information, and maintain a high level of

Qualifications

• Significant experience supporting senior executives in fast-moving organizations.
• Demonstrated experience handling confidential or sensitive information.
• Experience supporting multiple functions, investments, or strategic initiatives is a plus.

Responsibilities

• Operate as an AI-native executive partner, using AI tools to organize information and manage complex workflows.
• Build systems that maintain memory and context across meetings, decisions, and workstreams.
• Develop AI-enabled routines to increase executive support effectiveness and scale.
• Manage a complex executive portfolio with clear separation of contexts across workstreams and stakeholders.
• Be a trusted partner with high judgment and discretion handling sensitive information.
• Navigate the organization with a strong mental map of stakeholders and dynamics.

Skills

AI-native mindset

Exceptional judgment

High trust and discretion

Systems thinker

Organizational intelligence

Intellectual agility

Attention to detail

Ambiguity tolerance

Proactive ownership

Job description

About AI Labs

AI Labs operates at the intersection of AI, product, engineering, company building, investing, and M&A. We move quickly across a portfolio of companies, products, and strategic initiatives, often working on highly sensitive and complex matters.

We are building an AI-native operating model—not simply using AI as a productivity tool, but rethinking how work gets done when people, agents, data, and automation work together. This role will be an important part of that model.

The Role

We are looking for an exceptional Executive Assistant to support a senior AI Labs leader whose scope spans multiple distinct roles across the organization—from M&A and investing to product, engineering, operations, and company building. This is not a traditional administrative support role. The person who thrives here will combine the judgment, discretion, and organizational instincts of an exceptional executive partner with genuine curiosity and fluency in AI. They will use AI and automation to increase their own leverage, build systems that create context and continuity, and help their principal operate effectively across a large and rapidly changing portfolio.

The environment is fast-moving, highly interconnected, and often confidential. Success requires someone who can understand not only what is happening, but the context around it: which workstream something belongs to, who should be involved, what information can be shared, and where seemingly small mistakes could create meaningful business, legal, or reputational risk.

What You’ll Do

Operate as an AI-Native Executive Partner

• Use AI assistants, agents, and automation as a core part of how you work—not simply for summarization, but to organize information, maintain context, surface insights, and manage complex workflows.
• Build and maintain systems that create a reliable memory and context layer across meetings, decisions, relationships, commitments, and workstreams.
• Develop repeatable AI-enabled routines and automations that increase the effectiveness and scale of executive support.
• Understand the strengths and trade-offs of different AI tools and surfaces and determine which are appropriate for different types of work.
• Experiment with new tools and workflows as AI Labs continues to evolve its operating model.
• Serve as an early example of what an AI-native EA and executive support model can look like across AI Labs.

Manage a Complex Executive Portfolio

• Support an executive whose responsibilities span investing and M&A, product, engineering, operations, company building, and strategic advisory work.
• Maintain clear separation and context across distinct workstreams, stakeholders, entities, and confidential matters.
• Anticipate priorities, conflicts, dependencies, and information needs across a rapidly changing portfolio.
• Ensure the right people have the right context at the right time—without inadvertently exposing sensitive information.
• Manage a high volume of meetings, communications, decisions, follow-ups, and competing priorities with precision.

Be a Trusted Partner

• Exercise exceptional judgment when handling confidential, legally sensitive, commercially sensitive, and personally sensitive information.
• Build enough understanding of the organization to know when something is routine and when it requires additional care or escalation.
• Operate with a high degree of independence while knowing when to ask questions or seek guidance.
• Become a trusted point of continuity for the executive and the broader network of leaders, founders, operators, and partners around them.

Navigate the Organization

• Develop and maintain a strong mental map of AI Labs, Salesforce, portfolio companies, and key external stakeholders.
• Understand relationships, influence, decision rights, and organizational dynamics—not simply titles and reporting lines.
• Connect information and people across teams while respecting appropriate boundaries.
• Help the executive stay ahead of important relationships, commitments, decisions, and organizational changes.

What We’re Looking For

We are looking for someone who combines outstanding executive support fundamentals with the curiosity and adaptability required for an AI-native organization.

AI-native mindset. You actively use modern AI tools and are excited about building AI into your daily workflows. You understand—or are eager to deeply learn—prompting, agents, automation, context management, and emerging AI tools.
Exceptional judgment. You can operate in environments where context matters and where seemingly small decisions—who is included in a conversation, what information is shared, how something is documented—can have significant consequences.
High trust and discretion. You can be trusted with highly confidential company, transaction, personnel, and personal information.
Systems thinker. You don't just complete tasks; you build systems that make recurring work easier, more reliable, and more scalable.
Organizational intelligence. You naturally understand people, relationships, influence, and organizational dynamics and can maintain a sophisticated map of how the pieces fit together.
Intellectual agility. You are comfortable moving quickly between very different domains and can understand enough context to recognize what matters, what is different, and what cannot be conflated.
Extreme attention to detail. You operate with care and precision, particularly when working across confidential or legally sensitive matters.
Comfort with pace and ambiguity. You enjoy environments where priorities evolve quickly, information is incomplete, and the path forward is not always predefined.
Proactive ownership. You anticipate what is needed rather than waiting to be told what to do.

Preferred Experience

• Significant experience supporting senior executives in fast-moving, complex organizations.
• Demonstrated experience managing highly confidential or sensitive information.
• Experience supporting executives across multiple functions, businesses, investments, or strategic initiatives.
• Strong familiarity with modern AI tools and demonstrated use of AI to improve personal or team workflows.
• Experience in technology, startups, venture capital, private equity, M&A, product, engineering, or similarly dynamic environments is helpful but not required.
• San Francisco-based or able to work closely with a San Francisco-based executive.

What Success Looks Like

Within this role, success means the executive can operate across an unusually broad portfolio without losing context, dropping important commitments, or creating unnecessary risk.

Over time, the EA should become a trusted extension of the executive: understanding the people, priorities, sensitivities, and relationships around the work while building AI-enabled systems that allow both the executive and the broader organization to operate with greater speed and leverage.
Just as importantly, this person will help demonstrate what executive support can become in an AI-native organization—not AI replacing the fundamentals of great executive partnership, but AI allowing an exceptional EA to operate at an entirely different level of scale.