Chief of Staff, CEO

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 #1 provider 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. With a distributed global workforce and employee hubs in New York City, San Francisco, London, and Sydney, Attentive’s team has been consistently recognized for its performance and culture. We’re proud to be included in Deloitte’s Fast 500 (four years running!), LinkedIn’s Top Startups , Forbes’ Cloud 100 (five years running!), Inc.’s Best Workplaces , and the Human Rights Campaign Foundation's Corporate Equality Index ! 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