Director, Customer Success Operations & Strategy (Remote, US)

About Sayari:

Sayari is a risk intelligence provider that equips the public and private sectors with immediate visibility into complex commercial relationships by delivering the largest commercially available collection of corporate and trade data from over 250 jurisdictions worldwide. Sayari's solutions enable risk resilience, mission-critical investigations, and better economic decisions.

Headquartered in Washington, D.C., its solutions are trusted by Fortune 500 companies, financial institutions, and government agencies, and are used globally by thousands of users in over 35 countries. Funded by world-class investors, with a strategic $228 million investment by TPG Inc. (NASDAQ: TPG) in 2024, Sayari has been recognized by the Inc. 5000 and the Deloitte Technology Fast 500 as one of the fastest growing private companies in the United States and was featured as one of Inc.’s “Best Workplaces” for 2025.

Position Description

As Director of Customer Success Operations & Strategy, you will lead the design and execution of a scalable operating model for our global post-sale teams—including CS, Support, and Professional Services. Your mandate is to ensure that every customer touchpoint is aligned, actionable, and contributes to value realization and retention.

You’ll be responsible for customer journey mapping, end-to-end retention forecasting, and driving automation and process excellence via platforms like Gainsight and Salesforce. You will also bring a forward-leaning perspective on the use of AI tools and workflow technologies to increase CSM productivity, reduce churn risk, and optimize the customer lifecycle.

This role requires both systems-level thinking and hands-on execution, with high collaboration across GMs, Product, RevOps, and Finance.

Job 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
  
  
  

Required Skills & Experience

• 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
  
  
  

Preferred Skills & Experience

• 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
  
  
  

Sayari is an equal opportunity employer and strongly encourages diverse candidates to apply. We believe diversity and inclusion mean our team members should reflect the diversity of the United States. No employee or applicant will face discrimination or harassment based on race, color, ethnicity, religion, age, gender, gender identity or expression, sexual orientation, disability status, veteran status, genetics, or political affiliation. We strongly encourage applicants of all backgrounds to apply.

The target base salary for this position is $175,000 - $200,000 plus bonus and equity. Final offer amounts are determined by multiple factors including location, local market variances, candidate experience and expertise, internal peer equity, and may vary from the amounts listed above.