Chief of Staff

Remote
Full Time Mid Level 5+ years

Posted 3 weeks ago

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About This Role

This Chief of Staff role will lead operational rhythms and client-facing delivery, especially for modern AI solutions, acting as a force-multiplier to the executive team. The role focuses on aligning priorities, running cross-functional projects, and ensuring crisp execution from intake to impact.

Responsibilities

  • Partner with the Managing Director of AI and executive team to translate priorities into sequenced plans, resourcing, and measurable outcomes
  • Maintain focus and accountability on near-term deliverables and long-term goals; surface risks and options early
  • Own end-to-end delivery on multiple client engagements involving AI-enabled solutions
  • Run discovery to surface use cases, success metrics, risks, and change-management needs; translate findings into scopes, timelines, and clear acceptance criteria
  • Coordinate solution build-outs with internal teammates and external partners
  • Set lightweight evaluation routines (accuracy, latency, cost), prompt/playbook management, basic safety/guardrail checks, and UAT plans
  • Track time against SOWs, flag changes early, manage subcontractors, and ensure on-budget delivery with clear documentation
  • Design and continuously improve the operating system for work
  • Manage staffing assignments and subcontractor contributions across concurrent workstreams
  • Prepare agendas, briefings, and executive-ready presentations; synthesize complex information into actionable insights

Requirements

  • 5+ years in operations, client services, program/project management, or strategic support roles with direct ownership of client-facing delivery
  • Demonstrated success leading multi-stakeholder projects end-to-end (scope, timelines, budgets, risk, and change management)
  • AI fluency: understands common LLM-enabled use cases; can shape prompts/playbooks, evaluate quality at a basic level, and choose appropriate off-the-shelf tools or vendors
  • High proficiency with Google Workspace, Asana/Notion, Slack, and comfort with modern web and content tools
  • Experience preparing polished executive documents and presentations
  • Commitment to ethical practices and responsible AI

Qualifications

  • Bachelor’s degree or equivalent experience
  • 5+ years in operations, client services, program/project management, or strategic support roles with direct ownership of client-facing delivery.

Nice to Have

  • Familiarity with no/low-code automation (e.g., Zapier/Make)
  • Knowledge bases
  • Responsible AI considerations (privacy, data handling, consent)

Skills

Google Workspace * AI * Asana * LLM * Notion * Slack * Make * Zapier *

* Required skills

About Swooped

A rapidly growing, AI-powered customer communications platform used by thousands of companies worldwide to drive revenue, achieve faster resolutions, and scale effectively. The organization integrates voice, SMS, WhatsApp, and AI into a single, seamless workspace.

Technology
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