Chief of Staff, CEO

Attentive•New York, NY

5d•$200,000 - $250,000•Hybrid

About The Position

Attentive is hiring a Chief of Staff to work directly with the CEO as the company transforms its products and operations into an AI-native business. The role helps translate the company’s product vision into decisions, priorities, and results, while addressing consequential problems and shaping the company’s direction. The position is based in Attentive’s New York office and follows a hybrid schedule, with in-office collaboration Tuesday through Thursday each week. The Chief of Staff will serve as the CEO’s thought partner, lead strategic initiatives, manage company operating rhythms, and improve how the organization operates, including through practical applications of AI. For US-based applicants, the full-time position offers a base salary of $200,000–$250,000 annually, plus equity and benefits. Attentive is an equal opportunity employer and is committed to providing reasonable accommodations for candidates with disabilities.

Requirements

5–10 years of experience.
Exceptional analytical ability and judgment, including the ability to master unfamiliar topics quickly, ask incisive questions, and turn complex information into clear recommendations.
Genuine excitement about Attentive’s mission and ambition to shape the future of marketing.
Comfort with continuous and direct feedback, willingness to apply feedback quickly, and openness to changing one’s mind when evidence changes.
Demonstrated ability to influence senior leaders and drive cross-functional work without formal authority.
Clear and concise communication skills.
High ownership and low ego, with the ability to shape solutions to ambiguous strategic problems and manage operational details needed to advance them.
Active AI practitioner with strong conviction in AI’s potential to change how companies operate, supported by hands-on experience.

Nice To Haves

At least 2 years of experience in consulting, banking, or a real startup is strongly preferred.

Responsibilities

Serve as the CEO’s right hand and thought partner by pressure-testing ideas, framing tradeoffs, and helping turn major decisions into action across the organization.
Set and manage company operating rhythms, including OKRs, All Hands, and monthly business reviews, ensuring clear decisions, accountability, and follow-through.
Lead recurring and one-off strategic initiatives from problem definition and recommendation development through execution.
Translate company priorities into clear owners, milestones, and next steps; surface risks and resolve issues that fall between teams.
Prepare analyses, communications, and documents, such as executive agendas, to support decisions by the CEO and leadership team and keep the company aligned.
Improve how the company operates, including identifying practical uses of AI to increase speed and effectiveness.