Job Description

About the Role

We’re looking for a Chief of Staff to our Chief Revenue Officer (CRO) to help drive alignment, operating rigor, and execution across Attentive’s end-to-end Revenue organization (Sales, Customer Success, Services & Support, Revenue Operations, Enablement, Partnerships, and other GTM functions as relevant).

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 ensuring the right decisions get made quickly with strong follow-through. You’ll bring structure to ambiguity, elevate business visibility through crisp insights and storytelling, and help leaders across Revenue move in lockstep against the company’s most important growth and retention goals.

This role is ideal for someone who thrives at the intersection of strategy + execution—equally comfortable shaping the narrative for executives and the Board, and rolling up their sleeves to drive cross-functional programs to completion. It’s a unique opportunity to sit at the center of a high-growth SaaS business and materially influence how Revenue scales.

• 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.
• Operationalize the CRO’s Priorities: Translate strategy into structured workstreams 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.

• 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).

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