Chief of Staff, CEO

Attentive

. Serve as the CEO’s right hand and thought partner .

Posted 11/5/2026full-timeNew York City • New York • United StatesLead💰 $200,000 - $250,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates exceptional analytical ability and judgment, with a strong focus on translating company priorities into actionable plans. Proven experience in leading strategic initiatives and improving operations through practical applications of AI.

Highest-signal resume keywords

Strategic Initiative LeadershipAnalytical AbilityCross-Functional InfluenceAI PractitionerClear Communication

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Analytical AbilityProblem DefinitionOperational ManagementAI ImplementationDecision-Making

Soft Skills

Influencing Senior LeadersClear CommunicationHigh OwnershipLow EgoAdaptability

Industry Keywords

ConsultingBankingStartupOKRsBusiness Reviews

About the role

Key responsibilities & impact

Serve as the CEO’s right hand and thought partner
Pressure-test ideas, frame tradeoffs, and turn major decisions into action
Set and manage company operating rhythms, including OKRs, All Hands, and monthly business reviews
Lead recurring and one-off strategic initiatives from problem definition through execution
Translate company priorities into owners, milestones, and next steps
Surface risks and resolve issues between teams
Prepare analyses, communications, and executive documents for the CEO and leadership team
Improve company operations, including practical uses of AI to increase speed and effectiveness

Requirements

What you’ll need

5–10 years of experience
Minimum 2 years in consulting, banking, or a real startup strongly preferred
Exceptional analytical ability and judgment
Ability to quickly master unfamiliar topics and turn complex information into clear recommendations
Genuine excitement about Attentive’s mission and ambition to shape the future of marketing
Comfortable with continuous and direct feedback
Ability to influence senior leaders and drive cross-functional work without formal authority
Clear and concise communication
High ownership and low ego
Ability to shape solutions for ambiguous strategic problems and handle operational details
Active AI practitioner with hands-on experience and strong conviction in AI’s potential to change how companies operate

Benefits

Comp & perks

Health and wellness benefits
Equity
Competitive perks and benefits
Employee resource groups through AWAKE
Reasonable accommodations for candidates with disabilities