Chief of Staff, Customer Success

Attentive® is the AI-powered mobile marketing platform transforming the way brands personalize consumer engagement. Attentive enables marketers to craft tailored journeys for every subscriber, driving higher recurring revenue and maximizing campaign performance. Activating real-time data from multiple channels and advanced AI, the platform personalizes content, tone, and timing to deliver 1:1 messages that truly resonate.

With a top-rated customer success team recognized on G2, Attentive partners with marketers to provide strategic guidance and optimize SMS and email campaigns. Trusted by leading global brands like Neiman Marcus, Samsung, Wayfair, and Dyson, Attentive ensures enterprise-grade compliance and deliverability, supporting trillions of interactions across more than 70 industries. To learn more or request a demo, visit www.attentive.com or follow us on LinkedIn, X (formerly Twitter), or Instagram.

Attentive’s growth has been recognized by Deloitte’s Fast 500, Linkedin’s Top Startups and Forbes Cloud 100 all thanks to the hard work from our global employees!

About the Role

We’re looking for a Chief of Staff to support our VP of Global Customer Success and VP of Services & Support – two leaders who drive Attentive’s post-sale Customer Experience organization. The role will report directly into the Chief of Staff to the CRO, working as part of the broader Office of the CRO to ensure alignment and execution across all revenue functions.

As Chief of Staff, you’ll serve as a strategic partner and operator—helping translate leadership vision into clear plans, driving execution across cross-functional programs, and ensuring our Customer Success and Services organizations are running with focus, clarity, and accountability. You’ll bring structure and rhythm to the teams’ priorities, streamline how decisions get made, and create visibility for leadership around performance and progress.

This role is ideal for someone who thrives at the intersection of strategy, operations, and execution—someone who can seamlessly move between big-picture problem-solving and the detailed coordination needed to bring ideas to life. This is a unique opportunity to gain visibility into the inner workings of a high-growth SaaS company, work directly with senior leadership, and make an immediate impact on our most important customer-facing priorities.

What You’ll Accomplish

• Drive Strategic Alignment: Partner with the VPs of Customer Success and Services & Support to set strategic priorities, structure leadership planning, and ensure alignment across GTM, Product, and Operations teams
• Operationalize Priorities: Translate leadership goals into clear workstreams with defined owners, timelines, and outcomes—ensuring cross-functional programs move from concept to measurable impact
• Own Business Cadence: Build and manage operating rhythms including QBRs, business reviews, forecasting sessions, and leadership meetings—driving accountability and follow-through on key deliverables
• Partner Across Functions: Act as a connector between post-sale functions (Customer Success, Services, Support) and other GTM teams (Sales, Marketing, RevOps), facilitating communication and collaboration
• Support Executive Decision-Making: Prepare materials and insights for leadership discussions, identify risks and trade-offs, and ensure the right information flows to the right stakeholders at the right time
• Strengthen Execution Discipline: Introduce frameworks, dashboards, and processes that improve transparency, speed, and consistency in how the organization operates and measures success
• Act as a Force Multiplier: Serve as an extension of GTM executives—anticipating needs, managing competing priorities, and keeping the organization focused on what matters most

Your Expertise

• 5-7+ years of experience in roles blending strategy, operations, and program management, such as: consulting, GTM Strategy, GTM Operations, Chief of Staff, or Strategic Program Management within a high-growth SaaS company
• Proven ability to act as an extension of senior executives, exercising sound judgment and decision-making on their behalf
• Track record of managing multiple priorities, shifting seamlessly between tactical execution and strategic planning
• Strong business acumen and comfort interpreting and communicating metrics, performance data, and strategic priorities
• Excellent written and verbal communication skills, with the ability to create executive-ready materials
• Adept at building relationships and influencing stakeholders at all levels
• Comfortable working independently, anticipating needs, and driving work forward without heavy direction
• Familiarity with SaaS GTM motions (sales, renewal, expansion), metrics, or program management; experience in Customer Success or related go-to-market functions is a plus
• Proficiency in tools like Google Workspace, Slack, and Salesforce

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 $150k - 200k annually + equity + benefits
• Equity is a substantial part of the total compensation package
• Our salary ranges are determined by role, level and location

#LI-AL1

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.