Chief of Staff – AI Integration
The COOL Company
Posted: 10/20/2026
Chief of Staff
Vetcove
Posted: 10/20/2026
Deputy Chief of Staff, SVP
New York University Tisch School of the Arts
Posted: 10/20/2026
GTM Associate – Chief of Staff to Post Sales Leader
Brandlight
Posted: 10/20/2026
Chief of Staff
Pindrop
Posted: 10/20/2026
Founder's Associate Program – 2x YC Founder
Jerry
Posted: 10/20/2026
Chief of Staff to the CEO – Integrator
NexScale
Posted: 10/19/2026
Applied AI Strategy Business Planning Lead – Chief of Staff
HP
Posted: 10/19/2026Cloud
Director, Chief of Staff – Hybrid Cloud
Hewlett Packard Enterprise
Posted: 10/19/2026Cloud
Director, Chief of Staff – Hybrid Cloud COO
Hewlett Packard Enterprise
Posted: 10/19/2026Cloud
Director, Chief of Staff – Hybrid Cloud
Hewlett Packard Enterprise
Posted: 10/19/2026Cloud
Chief of Staff
Trial Library
Posted: 10/17/2026
Chief of Staff, Science
Datavant
Posted: 10/16/2026
Chief of Staff, CCO
Ping Identity
Posted: 10/16/2026SQLTableau
Chief of Staff, Clinical
Headway
Posted: 10/16/2026
Chief of Staff
ElevenLabs
Posted: 10/16/2026
Chief of Staff
Urrly
Posted: 10/16/2026PythonSQL
Chief of Staff
Employer Direct Healthcare
Posted: 10/15/2026
Chief of Staff
Abby Care
Posted: 10/15/2026
Chief of Staff, CEO
Gainsight
Posted: 10/15/2026Chief of Staff – AI Integration
The COOL CompanyCore Competencies
Role fitCore Competencies
Use this summary to align your resume positioning with the role.
Demonstrates expertise in high-ownership business operations, strategic planning, and cross-functional collaboration, with a strong focus on implementing AI workflows and process improvements. Proficient in executive communication, project management, and analytical rigor to drive measurable business outcomes.
Highest-signal resume keywords
Business Operations ManagementAI Workflow ImplementationCross-Functional CollaborationExecutive CommunicationProject Management
About the role
Key responsibilities & impact- Work directly with the Founder & CEO as a high-trust, hands-on operator
- Own the CEO’s strategic operating cadence, including weekly priorities, leadership follow-ups, meeting preparation, decision logs, and status updates
- Convert CEO and leadership discussions into prioritized action registers with owners, deadlines, dependencies, and escalation paths
- Prepare concise executive briefs using approved sources such as CRM, meetings, project systems, and communications
- Surface missed commitments, risks, and cross-functional bottlenecks early
- Audit high-friction workflows across Sales, Account Management, Marketing, Product, Engineering, Finance, People, and Operations
- Design, prototype, and implement secure AI workflows and integrations
- Work with the CTO and security owners on access, permissions, privacy, vendor selection, data retention, accuracy checks, and human approval gates
- Move pilots into durable production processes with documentation, monitoring, training, assigned owners, and measurable results
- Build reporting on workflow usage, quality, time saved, cost, and business outcomes
- Run selected cross-functional initiatives, including growth projects, process redesign, and integration planning
- Partner with the People Team and department heads to establish clear roles, SMART goals, and leadership rhythms
- Improve business reviews and dashboards using leading and lagging indicators
- Draft internal communications and recommendations and obtain approvals before external messages or sensitive changes
Requirements
What you’ll need- 6+ years in high-ownership business operations, chief of staff, strategy and operations, consulting, product operations, or automation/transformation roles
- Meaningful time partnering with a founder or executive team strongly preferred
- Demonstrated record of shipping cross-functional changes and building reliable operating processes
- Hands-on fluency with current AI products, LLM workflows, automation platforms, APIs/integrations, and data systems
- Ability to prototype personally and work with engineers on production-grade implementations
- Strong command of CRM, spreadsheets, dashboards, project management, meeting intelligence, and structured documentation
- High analytical rigor, including defining baselines, evaluating ROI, measuring adoption, and investigating inaccurate or misleading outputs
- Exceptional written communication, project management, prioritization, stakeholder leadership, and executive judgment
- Sound security and confidentiality instincts; understanding of human-in-the-loop approvals and sensitive-data handling
- Calm under ambiguity, discreet, curious, resourceful, low-ego, and comfortable holding senior leaders accountable
- Advertising/media/MarTech experience is a plus, not a prerequisite
Benefits
Comp & perks- Competitive package to be finalized by the CEO and People Team
- Company benefits to be confirmed during recruiting
- Any incentive/equity eligibility to be confirmed during recruiting
- Regular in-person collaboration and travel as needed
ATS Keywords
✓ Tailor your resumeApplicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills
Business OperationsAI ProductsLLM WorkflowsAutomation PlatformsAPIs/IntegrationsCRMSpreadsheetsDashboardsProject ManagementAnalytical Rigor
Soft Skills
Written CommunicationPrioritizationStakeholder LeadershipCalm Under AmbiguityResourcefulness
Tools & Technologies
Project SystemsMeeting IntelligenceStructured Documentation
Industry Keywords
AdvertisingMediaMarTech