AI-Native Chief of Staff

New
P
PhoenixEcommerce software
Remote (U.S.)Full-Time
Salary not disclosed
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Job Details

Required Skills
Project ManagementQA AutomationMarket Research

Requirements

  • Bring strong business acumen and the ability to organize, drive accountability, and follow through on business priorities.
  • Build with modern AI tools and have shipped working automations, agents, or internal tools that real people use.
  • Be able to describe recent work shipped with an AI agent and what that work replaced.
  • Operate autonomously, solve problems, and bring solutions and the resources needed to execute.
  • Write clear, concise research memos quickly, with checked numbers and named sources.
  • Think carefully and support opinions in strategy discussions with research and detailed knowledge.
  • Work confidently with senior leaders, department heads, partners, and major merchants; communicate clearly and respectfully.
  • Have thrived in a fast-moving, resource-constrained, high-intensity environment in recent years, or have built something independently.
  • DTC or direct response ecommerce business experience is a plus.
  • Founder, early operator, chief of staff, or founder's office experience at a rapidly scaling startup is a plus.
  • Living in South Florida or being able to travel there consistently is a plus.

Responsibilities

  • Prepare the weekly Companywide Alignment memo by gathering departmental updates and drafting from the week's meetings.
  • Track commitments from the memo, confirm owners and dates, unblock dependencies, and escalate slipping work to the CEO.
  • Research market segments, competitors, platform changes, merchants, and company data for strategy memos.
  • Evaluate partnership opportunities and coordinate cross-department plans to launch approved partnerships.
  • Join calls for major merchant deals and track commitments through onboarding, processing approval, campaign launch, and ramp-up.
  • Build an internal Phoenix brain using the CRM, company documents, roadmap, and meeting transcripts.
  • Structure and improve the CEO's AI agents, including their context, decision logic, routing, and feedback loops.
  • Work with department heads to identify workflows and help them build and run their own AI automations.
  • Assess tasks for potential automation with department heads before roles are opened, and help new hires start AI-native when hiring proceeds.
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