Chief of Staff, AI-Native

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee the CEO's operational framework, which involves follow-through, research, special projects, and interdepartmental communication.

• Assist in the preparation of the weekly Companywide Alignment memo by gathering departmental updates and drafting content from meetings.

• Monitor action items, responsible parties, timelines, and confirmations; resolve dependencies and escalate any lagging tasks.

• Conduct market and go-to-market research, including market sizing, competitor analyses, platform evaluations, and merchant insights.

• Participate in partnership discussions, assess partnership suitability, and manage approved partnerships from legal review to launch.

• Collaborate with product, engineering, client success, marketing, and other teams to successfully implement partnerships.

• Support major merchant agreements led by the CEO, ensuring that commitments translate into effective onboarding, implementation, payment processing, campaigns, and merchant ramp-up.

• Execute special projects from inception to completion, turning ideas into action within days.

• Create an internal Phoenix brain utilizing CRM data, documentation, roadmap details, and meeting transcripts.

• Enhance and advance the CEO's AI agent team, focusing on agent context, decision-making logic, routing, and learning mechanisms.

• Mentor department leaders to identify workflows and develop their own AI-driven automations.

• Analyze proposed staffing needs by breaking down roles into tasks and assessing what can be managed by AI prior to hiring.

• Ensure that new hires are AI-native when recruitment is necessary.

⛳️ Requirements

• Strong business insight.

• Proven ability to operate as a force multiplier across various business priorities.

• Experience in creating and implementing functional automations, agents, or internal tools utilized by actual users.

• Capability to identify the last three items delivered with an agent and their replacements.

• Comfort in learning through hands-on experience and independently resolving challenges.

• Strong research, analytical, and strategic thinking abilities.

• Proficiency in producing concise and accurate research memos within 48 hours, including verified figures and cited sources.

• Clear, efficient writing and excellent communication skills.

• Ability to collaborate effectively with senior leaders, partner executives, and significant merchants.

• Capacity to respectfully challenge department heads and foster accountability.

• Experience thriving in fast-paced, resource-limited, high-intensity startup settings recently, or having independently built something.

• Willingness to work with high standards, urgency, pressure, and considerable ownership.

• Major plus: residing in South Florida or frequently traveling there.

• Major plus: experience managing a direct-to-consumer or direct response ecommerce venture.

• Major plus: background as a founder, early-stage operator with outcome ownership, or chief of staff in a rapidly scaling startup.

🏝️ Benefits

• Opportunity to collaborate closely with the founder and CEO, particularly for candidates based in South Florida or those able to travel there frequently.

• Career advancement through an apprenticeship with the CEO.

• Potential for growth into future leadership positions based on ownership of outcomes.

• High-autonomy, high-ownership work culture.

• Exposure to company-wide strategy, operations, partnerships, go-to-market initiatives, and executive decision-making.

• Engage with modern AI tools and develop AI-native automations, agents, and internal resources.

• Mission-driven, performance-oriented culture.

• Direct feedback and a meritocratic workplace.

• Flexible remote work arrangement.