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rippling·Software Engineer·Onsite - System Design / Architecture·Senior

SeniorPrefer not to say
Jun 2026Remote

Summary

Rippling system design round focused entirely on building a rules engine for a corporate expense management product. The question had a lot of surface area and pushed into product thinking pretty quickly, which I wasn't fully expecting from a purely engineering interview.

Questions Asked (5)

Q1

Design a rules engine for a corporate credit card expense system where managers can define policies. You're given a function signature like evaluateRules(rules, expenses) where expenses are dictionaries with string keys and values. The system needs to flag violations for rules like no restaurant expense over $75, no airfare, no entertainment, and no expense over $250. What should the function return for use as an API response?

System DesignAPI & IntegrationsData Modeling
Author's notes

I started with the return type question because it felt like the safest entry point.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements and constraints, then propose a flexible rules engine design that separates rule definition from evaluation. Focus on the API response structure, ensuring it provides clear violation details and is extensible for future rule types.

Pro tip: Design the response to include not just violations but also metadata like rule IDs and expense references, making it easy for clients to display actionable feedback and for debugging. Also, consider performance implications for large expense lists and suggest optimizations like indexing or early exits.

1. Clarify Requirements

Ask questions to understand the scope: Are rules predefined or user-defined? What are the exact rule formats? How should violations be prioritized? This ensures the design meets actual needs.

2. Define Rule Representation

Propose a structured format for rules, such as objects with type, condition, and threshold. This allows parsing and evaluation without hardcoding each rule.

3. Design Evaluation Logic

Outline how to iterate through expenses and apply rules, handling different rule types (e.g., category-based, amount-based). Discuss trade-offs between simplicity and extensibility.

4. Define API Response Structure

Specify a JSON response that includes a list of violations, each with rule ID, expense ID, and message. Also include summary counts and possibly a status field.

5. Discuss Extensibility and Performance

Mention how to add new rule types without changing the core engine, and suggest optimizations like pre-filtering expenses or using indexes for large datasets.

Key Points to Mention

  • Separation of concerns: rule definition vs. rule evaluation
  • Use of a declarative rule format (e.g., JSON schema) for flexibility
  • API response should include violation details: rule ID, expense ID, message, and severity
  • Consideration of edge cases: multiple violations per expense, missing fields, currency handling
  • Performance: avoid O(n*m) by indexing or grouping expenses by category
  • Extensibility: plugin architecture or strategy pattern for new rule types

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

Q2

How would you represent rules in a way that's extensible to hundreds of different rule types, and how would you handle conflicts or precedence between rules?

System DesignTechnical Trade-offsAdaptability & Ambiguity
Author's notes

This is where I probably lost the most ground.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements and scale, then propose a declarative rule schema with a common interface and a registry for extensibility. Explain how to resolve conflicts using a precedence hierarchy and a deterministic conflict resolution strategy, and discuss trade-offs between flexibility and performance.

Pro tip: Emphasize that rules should be data-driven and versioned, and that conflict resolution should be configurable per domain to avoid hardcoding business logic.

1. Clarify Requirements and Constraints

Ask about the expected number of rules, update frequency, performance needs, and whether rules are user-defined or system-defined. This shapes the design.

2. Design a Declarative Rule Schema

Propose a common structure for rules (e.g., condition, action, priority, metadata) that can be extended for different types. Use a registry or plugin system to register new rule types.

3. Define Conflict Resolution and Precedence

Establish a precedence hierarchy (e.g., specificity, priority, recency) and a deterministic algorithm to resolve conflicts. Consider configurable strategies per rule type.

4. Address Scalability and Performance

Discuss indexing, caching, and lazy evaluation to handle hundreds of rule types efficiently. Mention trade-offs between generality and speed.

5. Discuss Extensibility and Maintenance

Explain how to add new rule types without modifying core logic, using interfaces and dependency injection. Highlight versioning and testing strategies.

Key Points to Mention

  • Use a common interface or abstract class for all rule types to ensure uniform handling.
  • Implement a rule registry or plugin architecture for dynamic registration of new rule types.
  • Define a precedence hierarchy (e.g., priority, specificity, recency) and a conflict resolution algorithm.
  • Consider using a rules engine (e.g., Drools) or building a custom DSL for complex conditions.
  • Ensure rules are data-driven and versioned to allow hot updates and rollback.
  • Discuss trade-offs: flexibility vs. performance, complexity vs. maintainability.

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

Q3

How would you build auditing and explanation into the system so that flagged expenses have traceable, human-readable justifications?

System DesignAPI & Integrations
Author's notes

Felt more comfortable here.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements: what types of expenses are flagged, who needs the explanations, and what level of detail is required. Then propose a layered architecture that captures audit events, stores rule-based justifications, and exposes them via APIs. Emphasize human-readable explanations generated from structured data, and discuss how to ensure traceability and immutability.

Pro tip: Design for explainability from the start: treat justifications as first-class data, not afterthoughts. Also, consider using a decision log pattern to record every rule evaluation and its outcome, which simplifies debugging and compliance.

1. Clarify requirements and constraints

Ask about the scale, regulatory needs, and who consumes the explanations (e.g., auditors, employees). Determine if explanations must be real-time or batch, and if they need to be immutable.

2. Design an audit event store

Propose an append-only log (e.g., using Kafka or a database table) that records every expense submission, rule evaluation, and flagging decision with timestamps and actor IDs. Ensure it's immutable and queryable.

3. Generate human-readable justifications

Use a rule engine that outputs structured reasons (e.g., 'amount exceeds limit by $X'). Then transform these into natural language templates or use an LLM to generate readable explanations, storing both structured and textual forms.

4. Expose explanations via APIs

Design REST or GraphQL endpoints to retrieve justifications for a given expense, with filtering by date, rule, or severity. Include versioning and pagination for large datasets.

5. Ensure traceability and monitoring

Add correlation IDs to trace a flag from ingestion to explanation. Implement monitoring for rule performance and explanation quality, and provide a UI for auditors to drill down.

Key Points to Mention

  • Immutable audit logs with append-only writes and cryptographic hashing for tamper-evidence.
  • Rule engine that produces structured decision data (e.g., Drools, JSON rules) for consistency.
  • Template-based natural language generation to ensure explanations are human-readable and consistent.
  • API design for retrieving explanations, including authentication, rate limiting, and versioning.
  • Data retention and privacy considerations (e.g., PII redaction in logs).
  • Integration with existing systems (e.g., expense management, HR) and event-driven architecture.

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

Q4

What product-oriented clarifications would you ask before building this, and how would managers select and manage the rules they want to enforce?

Product Sense & IdeationStakeholder ManagementAdaptability & Ambiguity
Author's notes

Honestly caught me a bit flat-footed because I was still in engineering mode.

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AI HintsAI Generated

Suggested Approach

Start by framing the problem: identify the core product (e.g., a rules engine) and its users (managers). Then, list key clarifications around goals, constraints, and success metrics, and propose a manager-friendly rule management design that balances power and usability.

Pro tip: Show empathy for managers by acknowledging their non-technical background and suggesting a UI with templates, previews, and audit logs. Also, tie clarifications to measurable outcomes like adoption and error rates.

1. Clarify Product Goals and Scope

Ask about the problem being solved, target users, and what success looks like. Determine if the rules engine is for internal ops, customer-facing, or both.

2. Identify Constraints and Requirements

Inquire about technical constraints (e.g., latency, scale), compliance needs, and integration points. Understand what rules must be supported and their complexity.

3. Design for Manager Usability

Propose a rule management interface that allows managers to select, configure, and prioritize rules without coding. Include features like templates, validation, and simulation.

4. Define Governance and Lifecycle

Outline how rules are versioned, tested, deployed, and retired. Suggest role-based access and approval workflows to prevent misuse.

5. Measure and Iterate

Recommend metrics to track rule effectiveness and manager adoption. Plan for feedback loops to refine the system.

Key Points to Mention

  • Clarify the specific business problem and how rules will be used (e.g., payroll, compliance, approvals).
  • Ask about non-functional requirements: performance, scalability, security, and auditability.
  • Propose a no-code/low-code rule builder with drag-and-drop or form-based configuration.
  • Include rule testing and simulation to let managers preview outcomes before enforcement.
  • Suggest role-based permissions and approval workflows to manage rule changes.
  • Define success metrics such as rule adoption rate, error reduction, and time saved for managers.

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

Q5

How would you approach performance and scalability for this rules evaluation system as the number of rules and expenses grows?

System DesignTechnical Trade-offs
Author's notes

Talked through short-circuiting evaluation on hard-block rules and batching expense checks.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the current architecture and scale (number of rules, expenses, evaluation frequency) to ground your answer. Then propose a layered strategy: optimize rule evaluation with indexing and caching, scale horizontally with partitioning, and consider architectural shifts like precomputation or incremental evaluation. Emphasize trade-offs between latency, consistency, and cost.

Pro tip: Quantify the impact of your optimizations (e.g., 'caching reduces evaluations by 80%') and mention how you'd measure success with metrics like p99 latency and throughput. This shows you think in terms of business outcomes, not just technical solutions.

1. Clarify Requirements and Current Bottlenecks

Ask about the current scale (number of rules, expenses, evaluation frequency), latency requirements, and any known performance issues. This ensures your answer is tailored to the actual problem.

2. Optimize Rule Evaluation

Propose algorithmic improvements: index rules by expense attributes, use decision trees or Rete algorithm for efficient matching, and cache frequent evaluation results. This reduces per-evaluation cost.

3. Scale Horizontally and Partition

Shard rules and expenses by tenant or category to distribute load, and use parallel processing for independent rules. This allows linear scaling with added resources.

4. Consider Architectural Shifts

For extreme scale, evaluate precomputing rule outcomes, incremental evaluation (only re-evaluate affected rules when data changes), or moving to a stream-processing model. Discuss trade-offs with consistency and complexity.

5. Monitor, Measure, and Iterate

Define key metrics (latency, throughput, error rates) and set up monitoring to identify bottlenecks. Use load testing to validate scalability and guide further optimizations.

Key Points to Mention

  • Caching strategies (e.g., memoization of rule results, Redis cache)
  • Indexing and efficient data structures (e.g., hash maps, tries, Rete algorithm)
  • Horizontal scaling and sharding (e.g., by tenant or expense category)
  • Asynchronous or parallel evaluation (e.g., using worker pools, message queues)
  • Precomputation and incremental evaluation to avoid full re-evaluation
  • Trade-offs between latency, consistency, cost, and complexity

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