Chief of Staff, CRO

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

We’re looking for a Chief of Staff to our Chief Revenue Officer (CRO) to help drive alignment, operating rigor, AI-enabled innovation, and execution across Attentive’s end-to-end Revenue organization, including Sales, Customer Success, Services & Support, Revenue Operations, Enablement, Partnerships, and other GTM functions. The Chief of Staff will attend weekly C-Level Executive meetings as well as all quarterly Board Meetings.

Reporting directly to the CRO, you’ll serve as a trusted thought partner and force multiplier, translating the CRO’s strategy into clear priorities, building the operating system that keeps the org on track, and helping the Revenue organization adopt smarter, more scalable ways of working. A key part of this role will be identifying, prioritizing, and driving AI initiatives across GTM–from improving seller and CSM productivity, to elevating forecasting and business insights, to enabling more effective customer engagement and internal decision-making.

This role is ideal for someone who thrives at the intersection of strategy, execution, and innovation — equally comfortable shaping the narrative for executives and the Board, rolling up their sleeves to drive cross-functional programs to completion, and partnering with teams to turn emerging AI opportunities into practical business outcomes. It’s a unique opportunity to sit at the center of a high-growth SaaS business and materially influence how Revenue scales in an increasingly AI-enabled operating environment.

What You’ll Accomplish

• Drive Revenue Org Strategic Alignment: Partner with the CRO to set and refine Revenue priorities, ensure clarity of direction, and align leaders across Sales, CS, RevOps, and other GTM teams on what matters most
• Lead AI Innovation Across GTM: Identify, prioritize, and drive AI-enabled initiatives that improve productivity, decision-making, customer engagement, forecasting, and execution across the Revenue organization
• Operationalize the CRO’s Priorities: Translate strategy into structured work streams with clear owners, milestones, success metrics, and escalation paths—driving execution from concept to measurable impact
• Own the CRO Operating Cadence: Build and run the operating rhythms that keep the business moving (weekly leadership meetings, monthly business reviews, QBRs, forecasting/commit cadences, planning cycles, and key internal readouts)
• Enable High-Quality Executive Decisions: Develop decision memos, dashboards, and pre-reads; synthesize trade-offs; identify risks and dependencies; and ensure decisions are documented and executed
• Elevate Business Performance Storytelling: Create clear, executive-ready narratives on performance, drivers, risks, and opportunities—supporting internal leadership communications and Board-level materials as needed
• Strengthen Cross-Functional Execution: Act as a connector across Revenue and key partners (Product, Finance, Marketing, Legal, etc.), improving collaboration, communication, and speed of execution across a matrixed org
• Drive Planning and Prioritization: Support annual and quarterly planning, including goal-setting, capacity planning inputs, resource trade-offs, and tracking execution against commitments
• Be a Force Multiplier for the CRO: Anticipate needs, manage competing priorities, unblock leaders, and keep the organization focused—operating as a reliable extension of the CRO

Your Expertise

• 5–8+ years of experience in roles blending strategy, operations, and program leadership (Chief of Staff, Revenue/GTM Strategy & Ops, BizOps, Strategic Program Management, Investment Banking, or Management Consulting)
• Demonstrated ability to act as an extension of a senior executive, exercising strong judgment and discretion
• Proven track record driving alignment and execution across complex, cross-functional stakeholders
• Strong analytical toolkit—able to move from messy inputs to clear insights, structured plans, and data-informed recommendations
• Excellent written and verbal communication skills; can produce executive-ready materials and facilitate senior leadership discussions with confidence
• Highly organized, proactive, adaptable; comfortable operating in ambiguity and driving work forward with minimal direction
• Understanding of SaaS go-to-market motions (pipeline, forecasting, renewal/retention, expansion, services, and customer experience) is a strong plus
• Proficiency with tools like Google Workspace, Slack, and Salesforce (and comfort learning new systems quickly)

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 $180,000 - $215,000 annually + variable compensation + equity + benefits
• Our salary ranges are determined by role, level and location

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