R
Sr. Manager, Customer Success Strategy & Operations
Retool
Remote (San Francisco, New York · New York, New York)
Senior Level
Posted 5 days ago
Skills
Strategic Planning
Data Analysis
Customer Success
Operations Management
Stakeholder Management
Performance Metrics
Business Intelligence
Automation
Artificial Intelligence
Cross-functional Collaboration
Forecasting
Customer Lifecycle Management
Analytical Thinking
Leadership
Process Improvement
About the Role
WHY WE’RE LOOKING FOR YOU:
Our post-sale organization is evolving quickly, and we need someone who can bring structure, clarity, and direction—not just reporting. This role is about defining what great looks like across Technical Customer Experience (TCX) and Customer Success, identifying where we’re falling short, and helping leadership make better, faster decisions.
This is a high-impact, high-visibility role that sits at the center of how we scale customer outcomes. You’ll help move the organization from reactive to proactive—shaping strategy, not just measuring it. You’ll also leverage modern analytics, automation, and emerging AI capabilities to accelerate insights and improve how we operate—but this is not a systems or reporting role. We’re looking for someone who can interpret the data, challenge assumptions, and influence direction.
WHO YOU’LL WORK WITH:
You’ll partner closely with Technical Customer Experience and Customer Success leadership, acting as a strategic advisor on performance, priorities, and planning.
You’ll also collaborate cross-functionally with RevOps, Finance, and Product to ensure alignment between customer strategy, business goals, and operational execution. This role offers meaningful exposure to executive-level decision-making and requires someone comfortable engaging at that level.
WHAT YOU’LL DO:
- Define and evolve key metrics across customer health, engagement, retention, and expansion—and ensure they actually drive behavior
- Deliver clear, opinionated insights and recommendations that inform strategy and planning (not just surface data)
- Conduct deep-dive analyses to uncover trends, risks, and opportunities across the customer lifecycle
- Partner with leadership to design and refine segmentation, coverage models, and engagement strategies
- Identify gaps in how we operate across TCX and Customer Success, and drive alignment on how to improve
- Leverage automation and AI-driven insights to accelerate analysis, improve forecasting, and surface recommendations faster
- Collaborate with RevOps and Systems teams to ensure tools support strategic goals—without owning system administration or execution
THE SKILLSET YOU’LL BRING:
- Strong analytical and strategic thinking skills—you don’t just report on data, you form a point of view and push for action
- Experience supporting Customer Success, Technical Customer Experience, or post-sale functions in a high-growth environment
- Proven ability to influence senior stakeholders and challenge thinking when needed—you’re a partner, not an order-taker
- Comfort operating in ambiguity and helping define structure where it doesn’t yet exist
- Ability to connect the dots across data, customer behavior, and business outcomes
- Familiarity with modern data tools, automation, and AI-enabled workflows—you know how to use them to move faster, not just build more
- Low tolerance for busywork—you prioritize high-impact problems and focus on what actually moves the business
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