Director, Customer Success Operations

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!), and Inc.’s Best Workplaces.

About the Role

As the Director of Customer Success Operations at Attentive, you will lead and optimize the rhythm around revenue and retention performance for our Customer Success team. This role reports to the VP of Revenue Operations, partnering closely with CS Leadership. You will own the cadence, forecasting rigor, segmentation and capacity model, and data integrity required to run the CS business with clarity and accountability. You’ll combine strategic thinking with hands-on operational leadership–building scalable processes, delivering actionable insights, and ensuring our teams have the goals, tools, and customer health signal infrastructure to proactively reduce churn and accelerate growth.

• CS Quota & Goal-Setting: Own the end-to-end annual and quarterly goal-setting process for CS (retention/renewals and expansion, as applicable), including target methodology, goal allocation, and ongoing calibration in partnership with CS Leadership, RevOps, and Finance
• Renewals Forecasting & Model Operations: Build and run a high-rigor renewals forecasting operating rhythm—owning the renewal forecast model, inspection cadence, risk taxonomy, and early-warning mechanisms to improve predictability and drive proactive intervention
• Customer Revenue Model & Operations: Own the underlying customer revenue operating model (what renews when, where risk sits, what drives NDR/GRR outcomes) and translate it into clear operating mechanisms, dashboards, and processes that CS teams can run weekly
• Post-Sale Performance Insights: Deliver clear performance storytelling for the CS organization—drivers of churn/retention/expansion, cohort trends, and recommended actions—and partner with CS Leadership to turn insights into execution
• Customer Segmentation & Territory / Book Management: Define and maintain customer segmentation and book-of-business management principles; partner with CS Leadership to align coverage models to customer needs and business goals
• CS Capacity Planning: Own CS capacity and coverage planning (ratios, book sizing, ramp assumptions, workload drivers) and translate it into hiring/coverage recommendations in partnership with CS Leadership and FP&A
• CS Data Integrity & Operating Hygiene: Own post-sale data integrity standards (definitions, required fields, lifecycle stages) and enforce operating hygiene so forecasting, reporting, and workflows are reliable and scalable
• Team Leadership & Development: Lead a team of 5, defining the right org structure and assessing current coverage and operating mode. Build an enablement and quality bar that scales with the business

• Proven experience (8+ years) in Revenue Operations, Business Analytics, or related roles, preferably in a B2B SaaS company
• Excellent analytical skills, with the ability to analyze complex data sets and market dynamics
• Exceptional communication and presentation skills, with the ability to effectively articulate complex concepts
• Strong understanding of SaaS business models, go-to-market strategies, and customer success processes
• Demonstrated success in leading teams and driving cross-functional alignment across multiple stakeholders across all levels
• Strong leadership capabilities, with experience in building and developing high-performing teams

You'll get competitive perks and benefits, from health & wellness to equity, to help you bring your best self to work.

US based applicants:

- The US base salary range for this full-time position is $190,000-$240,000 annually + equity + benefits

- Our salary ranges are determined by role, level and location

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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.