Chief of Staff, AI-Native

Phoenix Ecommerce Technologies

. Run the CEO's operating system, including follow-through, research, special projects, and cross-department communication .

Posted 10/7/2026full-timeRemote • United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates strong business acumen and strategic thinking, with the ability to build and ship automations and internal tools. Proven experience in cross-department collaboration, effective communication, and managing partnerships in a fast-paced startup environment.

Highest-signal resume keywords

Business AcumenAutomation DevelopmentResearch and Analytical SkillsCross-Department CommunicationPartnership Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Automation DevelopmentMarket ResearchGTM ResearchData AnalysisConcise Memo WritingAI Agent DevelopmentWorkflow IdentificationTask BreakdownOnboarding ImplementationEcommerce Business Management

Soft Skills

Strong CommunicationProblem SolvingAccountability DrivingAutonomous LearningRespectful Challenging

Tools & Technologies

CRM SystemsInternal ToolsAI Agents

Industry Keywords

DTC BusinessDirect Response EcommerceStartup EnvironmentPartnership EvaluationMerchant Ramp-Up

About the role

Key responsibilities & impact

Run the CEO's operating system, including follow-through, research, special projects, and cross-department communication
Help prepare the weekly Companywide Alignment memo by collecting department updates and drafting from meetings
Track action items, owners, dates, and confirmations; unblock dependencies and escalate slipping work
Conduct market and GTM research, including market sizing, competitor teardowns, platform analysis, and merchant research
Join partnership calls, evaluate partnership fit, and manage approved partnerships from legal review through launch
Coordinate product, engineering, client success, marketing, and other departments to bring partnerships live
Support major merchant deals led by the CEO and ensure commitments become successful onboarding, implementation, payments, campaigns, and merchant ramp-up
Run special projects end to end, moving initiatives from idea to live in days
Build an internal Phoenix brain using CRM data, documentation, roadmap information, and meeting transcripts
Develop and improve the CEO's AI agent team, including agent context, decision logic, routing, and learning loops
Coach department heads to identify workflows and build their own AI automations
Evaluate proposed headcount by breaking roles into tasks and determining what AI can handle before hiring
Ensure new hires start AI-native when hiring is necessary

Requirements

What you’ll need

Strong business acumen
Experience operating as a force multiplier across business priorities
Experience building and shipping working automations, agents, or internal tools used by real people
Ability to name the last three things shipped with an agent and what they replaced
Comfortable learning by building and solving problems autonomously
Strong research, analytical, and strategic thinking skills
Ability to produce concise, accurate research memos within 48 hours, with checked numbers and named sources
Clear, fast writing and strong communication skills
Ability to work effectively with senior leaders, partner executives, and major merchants
Ability to respectfully challenge department heads and drive accountability
Experience thriving in fast, resource-constrained, high-intensity startup environments in recent years, or having built something independently
Willingness to work with high standards, urgency, pressure, and significant ownership
Huge plus: living in South Florida or traveling there consistently
Huge plus: experience running a DTC or direct response ecommerce business
Huge plus: experience as a founder, early operator with outcome ownership, or chief of staff/founder's office at a rapidly scaling startup

Benefits

Comp & perks

Opportunity to work closely with the founder and CEO, especially for candidates in South Florida or able to travel there consistently
Career development through an apprenticeship with the CEO
Opportunity to grow into future leadership roles based on owning outcomes
High-autonomy, high-ownership work environment
Exposure to company-wide strategy, operations, partnerships, GTM, and executive decision-making
Work with modern AI tools and build AI-native automations, agents, and internal tools
Mission-first, performance-driven culture
Direct feedback and meritocratic environment
Remote work arrangement