Freelance - AI-Enabled Chief of Staff

Role Description

We are seeking an AI-Enabled Chief of Staff to support a fast-moving executive operating within the AI, Web3 and trading technology space. This role is ideal for someone who thrives in highly autonomous environments, understands emerging AI workflows and can operate as both a strategic partner and operational driver.

The ideal candidate is deeply immersed in the evolving AI ecosystem and is comfortable navigating modern AI tools, agentic workflows and fast-paced communication across global teams and Web3 companies. This individual will play a critical role in streamlining operations, supporting executive priorities and helping scale AI-driven initiatives.

Key Responsibilities

• Manage executive scheduling, communications and operational workflows across multiple platforms and stakeholders.
• Support coordination and communication with AI, Web3 and crypto-related companies and partners.
• Utilize AI tools and platforms such as Claude AI, Cursor and related technologies to improve efficiency and productivity.
• Assist in building, managing and optimizing AI-driven workflows and agentic operational systems.
• Provide prompt engineering support and develop structured prompts for operational and strategic use cases.
• Manage and organize communications across Slack, Telegram and related collaboration tools.
• Support research and operational coordination related to prediction markets, trading environments and emerging AI technologies.
• Maintain organized systems, documentation and internal workflows to support executive operations.
• Stay current with AI trends, tools and advancements while proactively identifying opportunities for improvement and automation.
• Operate with a high level of discretion, autonomy and accountability in a fast-paced remote environment.

Qualifications

• Strong experience working with AI tools and AI-enabled workflows.
• Proficiency with Claude AI, Cursor and modern AI productivity platforms.
• Strong understanding of AI agents and agentic workflow concepts.
• Experience with prompt engineering and structured AI prompting techniques.
• Experience supporting executives, founders or leadership teams in a Chief of Staff, Executive Assistant or operational support capacity.
• Familiarity with Web3, crypto, USDC, prediction markets or trading-related environments.
• Knowledge of Slack AI bots, workflow automations and modern collaboration tools.
• Strong written communication and organizational skills.
• Ability to work independently with minimal oversight while managing multiple priorities.
• Comfortable working late hours aligned with the New York timezone.
• Comfortable using Slack, Telegram and remote collaboration tools daily.
• Strong attention to detail, operational thinking and problem-solving ability.

Preferred Traits

• Autonomous and proactive
• Fast learner with strong adaptability
• Tech-native and highly AI-curious
• Operationally organized and resourceful
• Direct and effective communicator
• Excited about emerging AI technologies and experimentation

Work Setup

This role will initially begin as a part-time engagement with the potential to scale into a full-time position based on business needs and overall fit.

Company Description

You will be working as a contractor under the The People Group company name, therefore you are not a direct employee and only work as a contractor for our business. The benefit of this structure means, all of our clients sign contracts directly with The People Group and not you as the Contractor, therefore you are protected as a remote contractor as The People Group takes care of the client service side of the function.