The Chief of Staff will support the CRO by aligning revenue strategies, overseeing operations, enhancing decision-making, and improving cross-functional execution within the revenue organization.
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
#LI-NR1
By applying for this position, your data will be processed as per Attentive's Privacy Policy.
Attentive Company Values
Default to Action - Move swiftly and with purpose
Be One Unstoppable Team - Rally as each other’s champions
Champion the Customer - Our success is defined by our customers' success
Act Like an Owner - Take responsibility for Attentive’s success
Learn more about AWAKE, Attentive’s collective of employee resource groups.
If you do not meet all the requirements listed here, we still encourage you to apply! No job description is perfect, and we may also have another opportunity that closely matches your skills and experience.
At Attentive, we know that our Company's strength lies in the diversity of our employees. Attentive is an Equal Opportunity Employer and we welcome applicants from all backgrounds. Our policy is to provide equal employment opportunities for all employees, applicants and covered individuals regardless of protected characteristics. We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation. Attentive is also committed to providing reasonable accommodations for candidates with disabilities. If you need any assistance or reasonable accommodations, please let your recruiter know.
Similar Jobs
Information Technology • Cybersecurity
Huntress seeks a Senior Commercial Counsel to negotiate customer and vendor contracts, improve legal processes, and support global expansion efforts.
Top Skills:
Legal Ai ToolsSaas Contracts
Artificial Intelligence • Cloud • Software
As an Account Executive at Vercel, you will manage key enterprise accounts, drive revenue, and lead strategic negotiations while engaging with senior stakeholders.
Top Skills:
AICloud PlatformsDeveloper ToolingMlSaaSWeb Infrastructure
Security • Cybersecurity
The AI System Architect will oversee AI integration strategy, system governance, and architecture for enterprise applications, leading a technical team and shaping AI initiatives across platforms.
Top Skills:
ChatgptClaudeEltETLGraphQLHibobJIRANetSuiteRestSalesforceWorkato
What you need to know about the Colorado Tech Scene
With a business-friendly climate and research universities like CU Boulder and Colorado State, Colorado has made a name for itself as a startup ecosystem. The state boasts a skilled workforce and high quality of life thanks to its affordable housing, vibrant cultural scene and unparalleled opportunities for outdoor recreation. Colorado is also home to the National Renewable Energy Laboratory, helping cement its status as a hub for renewable energy innovation.
Key Facts About Colorado Tech
- Number of Tech Workers: 260,000; 8.5% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Lockheed Martin, Century Link, Comcast, BAE Systems, Level 3
- Key Industries: Software, artificial intelligence, aerospace, e-commerce, fintech, healthtech
- Funding Landscape: $4.9 billion in VC funding in 2024 (Pitchbook)
- Notable Investors: Access Venture Partners, Ridgeline Ventures, Techstars, Blackhorn Ventures
- Research Centers and Universities: Colorado School of Mines, University of Colorado Boulder, University of Denver, Colorado State University, Mesa Laboratory, Space Science Institute, National Center for Atmospheric Research, National Renewable Energy Laboratory, Gottlieb Institute
