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rippling·Software Engineer·Technical Phone Screen·Intermediate

Intermediate
May 2026

Summary

Rippling SWE interview centered on building an expense rule engine across three increasingly complex parts. The bar to pass was reaching at least Part 2, which tells you something about how they pace the problem.

Questions Asked (3)

Q1

Given a list of expenses (each with fields like amount, category, employee, and date) and a list of rules (each with conditions and an action like approve or flag), write code to evaluate every expense against every rule and return which rules match each expense.

Algorithms & Data StructuresSystem DesignTechnical Trade-offs
Author's notes

The core of the whole interview.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the problem: confirm the rule condition format, expected output, and performance constraints. Then outline a clean, extensible design that evaluates each expense against all rules, using a rule engine pattern and optimizing with indexing if needed. Finally, discuss trade-offs and potential improvements.

Pro tip: Mention that in a real system like Rippling, rules are often dynamic and user-defined, so a declarative approach (e.g., JSON-based conditions) with a generic evaluator is more maintainable than hardcoded logic. Also, consider early termination or indexing to avoid O(N*M) when scaling.

1. Clarify requirements and constraints

Ask about the rule condition format (e.g., field, operator, value), expected output structure, and any performance or scalability requirements. Confirm whether rules can have multiple conditions and how they combine (AND/OR).

2. Design data structures and interfaces

Define classes or types for Expense, Rule, Condition, and Action. Consider a generic Condition interface with an evaluate(expense) method, and a Rule composed of conditions and an action. This makes the system extensible.

3. Implement the evaluation logic

Iterate over each expense and each rule, evaluating the rule's conditions against the expense. Collect matching rules per expense. Use short-circuit evaluation for AND conditions to improve performance.

4. Optimize and discuss trade-offs

If the number of rules is large, consider indexing rules by category or field to reduce comparisons. Discuss time complexity (O(N*M) naive) and space complexity, and when optimization is necessary.

5. Test and handle edge cases

Write unit tests for various scenarios: no matching rules, multiple matching rules, complex conditions, and large datasets. Discuss error handling for invalid rules or missing fields.

Key Points to Mention

  • Rule engine design pattern for extensibility and maintainability
  • Time and space complexity analysis (O(N*M) vs optimized approaches)
  • Use of interfaces/abstractions for conditions and actions to support dynamic rules
  • Short-circuit evaluation and indexing for performance optimization
  • Handling edge cases like missing fields, invalid rules, and multiple matches
  • Trade-offs between simplicity and scalability, and when to optimize

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q2

How would you extend the rule engine to handle richer field types, surface match results to users, and deal with edge cases in a real product context?

Product Sense & IdeationSystem DesignData Modeling
Author's notes

This is where it shifted from pure coding to product thinking.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the product context and requirements, then propose a modular extension to the rule engine that supports richer field types through a type system and pluggable evaluators. Discuss how to surface match results via APIs and UI, and outline strategies for handling edge cases like nulls, type mismatches, and performance at scale.

Pro tip: Emphasize incremental delivery and backward compatibility: show how you'd roll out new field types without breaking existing rules, and how you'd gather user feedback to prioritize which types to support next.

1. Clarify requirements and use cases

Ask questions to understand what 'richer field types' means (e.g., dates, enums, nested objects) and how match results should be surfaced (e.g., API, UI, logs). Identify key edge cases from product and engineering perspectives.

2. Design extensible type system

Propose a pluggable architecture where each field type has a validator, comparator, and serializer. Use interfaces or abstract classes to allow adding new types without modifying core engine logic.

3. Surface match results effectively

Define a clear result object that includes matched rule IDs, field values, and reasons for match/mismatch. Expose via API and consider UI components like highlighting or tooltips to show why a rule matched.

4. Handle edge cases robustly

Address nulls, missing fields, type coercion, and conflicting rules. Implement fallback behaviors, logging, and alerts for anomalies. Ensure performance with indexing and caching for large datasets.

5. Plan rollout and iteration

Suggest a phased rollout with feature flags, backward compatibility, and metrics to track usage and errors. Iterate based on user feedback and monitor system health.

Key Points to Mention

  • Type system design: interfaces for validators, comparators, and serializers to support new field types.
  • Result surfacing: structured match results with reasons, exposed via API and UI for transparency.
  • Edge case handling: nulls, type mismatches, missing fields, and performance under load.
  • Backward compatibility: ensuring existing rules continue to work when adding new types.
  • Scalability: indexing, caching, and efficient evaluation for large rule sets.
  • User feedback loop: metrics and iteration to prioritize field types and improve UX.

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q3

Extend your rule engine so that rules can have compound conditions using AND and OR logic, including nested combinations. Evaluate the resulting boolean expression against each expense.

Algorithms & Data StructuresTechnical Trade-offsSystem Design
Author's notes

Knew this was coming the second they said 'three parts.' Still took me a minute to land on a clean representation.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements and constraints, then propose a design using the Composite pattern to represent compound conditions as a tree of AND/OR nodes and leaf conditions. Explain how to evaluate the tree recursively against an expense, and discuss trade-offs like short-circuit evaluation, extensibility, and performance.

Pro tip: Mention that you would use the Composite pattern to keep the design open for new logical operators (e.g., NOT) and that short-circuit evaluation can be a performance optimization. Also, consider how to handle edge cases like empty conditions or deeply nested expressions.

1. Clarify requirements and constraints

Ask about the expected complexity of conditions, performance requirements, and whether the rule engine needs to support additional operators like NOT. Confirm if conditions are evaluated per expense in real-time or batch.

2. Design the condition representation

Propose a composite structure where each condition is either a leaf (e.g., amount > 100) or a composite (AND/OR) containing child conditions. This allows arbitrary nesting and easy extension.

3. Implement evaluation logic

Describe a recursive evaluation function that traverses the condition tree, applying short-circuit logic for AND/OR. Ensure it returns a boolean for a given expense.

4. Discuss trade-offs and optimizations

Talk about performance implications of deep nesting, potential for caching results, and how to handle short-circuit evaluation to avoid unnecessary computations.

5. Consider integration and testing

Explain how this integrates with the existing rule engine, how to parse conditions from a DSL or JSON, and how to test complex nested conditions thoroughly.

Key Points to Mention

  • Composite pattern for representing nested AND/OR conditions
  • Recursive evaluation with short-circuit logic
  • Extensibility to support additional operators (e.g., NOT)
  • Performance considerations: caching, short-circuiting, and avoiding deep recursion
  • Parsing conditions from a configuration or DSL
  • Testing strategy for nested conditions and edge cases

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.