Director, Customer Success Operations & Strategy

Summary

Join Sayari as the Director of Customer Success Operations & Strategy and lead the design and execution of a scalable operating model for global post-sale teams. You will ensure every customer touchpoint is aligned and contributes to value realization and retention. Responsibilities include customer journey mapping, retention forecasting, driving automation and process excellence using platforms like Gainsight and Salesforce, and leveraging AI tools to increase CSM productivity. This role demands both strategic thinking and hands-on execution, requiring collaboration with various departments. The position offers a competitive salary, comprehensive benefits, and opportunities for growth within a supportive and innovative company culture. Sayari is committed to diversity, equity, and inclusion, and encourages applications from diverse candidates.

Requirements

• 8+ years in Customer Success Operations, Revenue Operations, or GTM strategy in a high-growth SaaS environment
• Demonstrated experience designing and embedding customer journeys within CS systems and processes
• Strong expertise in Gainsight, Salesforce, and journey-based lifecycle modeling
• Deep knowledge of retention forecasting, renewals infrastructure, and post-sale performance metrics
• Experience with AI tools that support CS workflow automation and proactive risk identification
• Strategic thinker with hands-on ability to build dashboards, automate playbooks, and improve workflows
• Proven ability to collaborate cross-functionally and influence at senior levels

Responsibilities

• Design and operationalize the end-to-end customer journey, including onboarding, adoption, value realization, and renewal—then translate that journey into system workflows, lifecycle metrics, and team accountability
• Build and continuously improve retention forecasting models and renewal process infrastructure to enable accurate risk tracking and proactive CS action
• Own Gainsight configuration and automation, including health scoring, playbooks, timeline cadences, and rule-based triggers to support scalable CSM workflows
• Evaluate and deploy AI-based tools that enhance CSM productivity, deliver proactive insights, and streamline customer engagement
• Lead the development of CSM coverage models, capacity planning, and segmentation strategies across post-sale functions
• Partner with GMs, Product, and CS leadership to align journey stages with customer value delivery and product engagement
• Define and track KPIs across the customer lifecycle, delivering dashboards and executive reporting on GRR, NRR, churn, usage, and retention risk
• Drive coordination across cross-functional partners—Finance, Sales, Systems, Product, Support—to ensure alignment across teams and tools

Preferred Qualifications

• Experience in B2B SaaS with complex or data-rich products
• Experience in US Federal and international government markets
• Familiarity with DealHub, Gong, Outreach, Hubspot, Zoominfo, LeanData
• Proven playbook in customer journey design, service blueprints, and lifecycle ops

Benefits

• 100% fully paid medical, vision, and dental for employees and their dependents
• Generous time off; we observe all US federal holidays, close our office for a winter break (12/24-12/31), in addition to granting 18 PTO days and 10 sick days
• Outstanding compensation package; competitive commissions for revenue roles and quarterly bonuses for non-revenue positions
• A strong commitment to diversity, equity, and inclusion
• Eligibility to participate in additional benefits such as 401k match up to 5%, 100% paid life insurance (up to $100,000 coverage),, and parental leave
• A collaborative and positive culture - your team will be as smart and driven as you
• Limitless growth and learning opportunities