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AI-Native Chief of Staff

1 hour, 41 minutes ago
United States
Full-time
Mid Level
AI (Artificial Intelligence)
Artificial Intelligence and Machine Learning
CRM
Apply Now
REIGN

REIGN

REIGN is a premium ad-supported and subscription streaming video on-demand service that offers a curated selection of African American and urban culture-themed content. With a user experience tailored for the urban culture audience, REIGN provides the ...

Media
1-10
Founded 2017
View All Jobs 9

Description

  • Manage CEO follow-through, inbox and calendar priorities, special projects, and cross-department communication.
  • Coordinate weekly companywide alignment, assign owners and deadlines, track commitments, and escalate risks early.
  • Conduct market, competitor, platform, merchant, and GTM research and turn findings into concise strategic memos.
  • Evaluate partnerships and manage approved initiatives from planning through legal, product, engineering, rollout, and announcement.
  • Support major CEO-led merchant deals through onboarding, payments approval, implementation, campaign launch, and ramp-up.
  • Lead rapid special projects from concept to launch, including an internal company knowledge brain and CEO AI-agent team.
  • Build and improve AI agents, automations, decision logic, workflows, and feedback loops for the CEO and departments.
  • Coach department heads to identify workflows for automation and build their own AI-enabled processes.
  • Assess proposed roles for automation opportunities before hiring while supporting final staffing decisions.
  • Provide operational insight and detailed analysis to help the CEO and executive team make important decisions.

Requirements

  • Strong business acumen with demonstrated ability to organize, drive accountability, and execute across departments.
  • Hands-on experience building and shipping AI automations, agents, or internal tools used by real people.
  • Comfort operating autonomously in fast-paced, resource-constrained, high-intensity startup environments.
  • Excellent written and verbal communication, including producing accurate, source-backed research memos within 48 hours.
  • Ability to think critically, solve problems independently, and bring solutions rather than simply escalating issues.
  • Confidence working with senior executives, challenging stakeholders respectfully, and driving commitments to completion.
  • Strong attention to detail and enthusiasm for operational follow-through, research, and execution.
  • High standards, urgency, ownership, and comfort in a performance-driven environment.
  • Experience as a founder, early-stage operator, chief of staff, or founder’s office member at a rapidly scaling startup (preferred).
  • Experience running a DTC or direct-response ecommerce business (preferred); South Florida residence or consistent travel availability is a plus.

Interested in this position?

Apply directly on the company website

Apply Now

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