Chief of Staff, CEO

Attentive; New York (NY); Hybrid; USD 200,000 - 250,000; Full time

Benefits offered by this job

Health & wellness

Equity

Job summary

Attentive is seeking a strategic operator to act as the CEO’s trusted right hand, shaping decisions and priorities while driving cross-functional initiatives. You will set operating rhythms and oversee executive-level reviews, translating company priorities into actionable ownership and milestones.

You will lead high-impact strategic programs, present analyses to the leadership team, and push AI-driven improvements across the organization.

Qualifications

• 5–10 years of experience in related roles.
• Minimum 2 years consulting, banking, or real startup experience preferred.
• Exceptional analytical ability and judgment.
• Genuine excitement about Attentive’s mission.
• Comfortable with feedback and willing to change mind when evidence dictates.

Responsibilities

• Serve as the CEO’s right hand and thought partner to frame tradeoffs and turn decisions into action.
• Set and manage operating rhythms (OKRs, All Hands, monthly business reviews) with accountability.
• Lead strategic initiatives from problem definition to execution and recommendations.
• Translate priorities into owners, milestones, and next steps; surface risks and resolve cross-team issues.
• Prepare analyses and executive-facing communications to aid leadership decisions.
• Improve operations with practical uses of AI to boost speed and effectiveness.

Skills

Analytical ability

Executive communication

Stakeholder influence

Strategic thinking

Owns initiatives

AI practitioner

Feedback culture

Cross-functional collaboration

Job description

Attentive® is the AI marketing platform for 1:1 personalization redefining the way brands and people connect. We’re the only marketing platform that combines powerful technology with human expertise to build authentic customer relationships. By unifying SMS, RCS, email, and push notifications, our AI-powered personalization engine delivers bespoke experiences that drive performance, revenue, and loyalty through real-time behavioral insights.

Recognized as the#1provider in SMS Marketing by G2, Attentive partners with more than 8,000 customers across 70+ industries. Leading global brands like Crate and Barrel, Urban Outfitters, and Carter’s work with us to enable billions of interactions that power tens of billions in revenue for our customers.

About the Role

Attentive is transforming both what we build and how we work. We’ve demonstrated consistent early wins with new AI products and have conviction in our ability to lead the AI future of marketing.

At the same time, we’re rebuilding Attentive as a truly AI-native company, rethinking how teams operate and get work done. This role works directly with the CEO at the center of that transformation, helping turn an ambitious product vision into decisions, company priorities, and results.

It’s an opportunity to take on consequential problems, learn quickly across the business, and have a direct hand in shaping what Attentive becomes.

This hybrid role is based in our New York office, with in-office collaboration Tuesday through Thursday each week.

What You’ll Accomplish

• Serve as the CEO’s right hand and thought partner: pressure-test ideas, frame tradeoffs, and work across the organization to turn major decisions into action.
• Set and manage the company’s operating rhythms, including OKRs, All Hands, and monthly business reviews, with clear decisions, accountability, and follow-through.
• Lead recurring and one-off strategic initiatives, from defining the problem and developing recommendations through execution.
• Translate company priorities into clear owners, milestones, and next steps; surface risks and resolve issues that fall between teams. Make sure things get done.
• Prepare analyses, communications, and documents (e.g. executive agendas) that help the CEO and leadership team make decisions and keep the company aligned.
• Improve how the company operates, including practical uses of AI to increase speed and effectiveness.

Your Expertise

• 5–10 years of experience; minimum 2 years consulting, banking, or real startup experience strongly preferred
• Exceptional analytical ability and judgment; can quickly master unfamiliar topics, ask incisive questions, and turn complex information into clear recommendations.
• Genuine excitement about Attentive’s mission and ambition to shape the future of marketing
• Comfortable with a culture of continuous and direct feedback, quick to apply it, and willing to change your mind when the evidence changes
• Demonstrated ability to influence senior leaders and drive cross-functional work without formal authority – especially when the evidence says you are right and they are wrong
• Clear and concise communicator
• High ownership and low ego. Can shape solutions for our most important, ambiguous strategic problems, and also handle the day-to-day operational details needed to move those solutions forward
• An active AI practitioner with strong conviction in its potential to change how companies operate, backed by hands-on experience

You’ll get competitive perks and benefits , from health & wellness to equity, to help you bring your best self to work.

For US based applicants:

• The US base salary range for this full-time position is $200,000 - $250,000 annually+ equity + benefits
• Our salary ranges are determined by role, level and location

Learn more about AWAKE , Attentive’s collective of employee resource groups.

Our company values diversity. To ensure that we comply with reporting requirements and to learn more about how we can increase diversity in our candidate pool, we invite you to voluntarily provide demographic information in a confidential survey at the end of this application. Providing this information is optional. It will not be accessible or used in the hiring process, and has no effect on your opportunity for employment.