Senior Manager, Retention Strategy & Intelligence

Okta•Chicago, IL

7d•Hybrid

About The Position

Okta is seeking a Senior Manager of Retention Strategy & Intelligence to own the development and operationalization of Guided Renewals, an AI-powered approach to proactive retention. This role involves partnering with the Renewals organization, collaborating with GTM functions, and working with the Technology, Data, and Insights (TDI) team. The primary focus is on the intelligence layer that drives retention, including identifying risk signals, building AI models for risk prediction and intervention recommendations, and leading field cadences to translate insights into action.

Requirements

7+ years across Customer Success, Renewals, Sales Enablement, or Revenue Operations with hands-on experience in data, analytics, or process automation.
Technical Fluency: Working knowledge of AI/ML, data architecture, and APIs.
Able to engage technical teams and translate business needs into solutions.
AI Systems Thinking: Able to design the logic and guardrails that govern AI behavior and ensure outputs are accurate and operationally useful.
Strategic Translator: Connects data signals to customer realities and understands how field teams actually work.
Product Thinking: Experience defining requirements, managing roadmaps, and iterating on user feedback.
Cross-Functional Leadership: Able to influence and align across Engineering, Data Science, Sales, CS, and Renewals.

Responsibilities

Own the definition, tracking, and interpretation of customer risk signals (usage, engagement, sentiment, commercial health).
Partner with TDI to establish signal weighting, scoring thresholds, and supporting data infrastructure.
Translate risk analysis into clear, actionable intelligence for field teams and leadership.
Define guidelines, guardrails, and decision logic for AI-driven retention recommendations.
Partner with TDI and Data Science to build models for personalized playbook recommendations.
Evaluate recommendation quality and drive model refinement.
Own product requirements for risk and recommendation tooling, defining UX, workflows, and outputs.
Manage the roadmap for risk and recommendation tooling from pilot to GA.
Ensure integration with CRM, ERP, and existing tools.
Design and lead recurring risk review cadences, including customer health reviews.
Embed cadences into Territory Planning, WIN Labs, and renewal cycles.
Serve as the primary field advocate, ensuring recommendations reduce cognitive load and drive decisive action.
Track performance across signal accuracy, recommendation acceptance, tooling adoption, and retention outcomes.
Establish feedback loops with field teams and TDI for continuous refinement.
Conduct root cause analysis on churn and contraction.