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Hopper·Software Engineer·Technical Phone Screen·Intermediate

IntermediatePrefer not to say
Jul 2026Remote

Summary

Hopper software engineer interview that was basically one meaty coding problem with some follow-ups tacked on. The core question sounds manageable until you actually sit down and think through all the edge cases.

Questions Asked (3)

Q1

Given a list of filename strings, implement a custom sort using a comparator that handles digit runs numerically, prioritizes digits over non-digits at the first differing position, and uses standard lexicographic order for non-digit parts.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

I thought I had this pretty quickly and started writing a comparator right away.

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AI HintsAI Generated

Suggested Approach

Clarify the exact comparison rules with the interviewer, then design a comparator that tokenizes strings into digit and non-digit runs. Implement the comparison by iterating through tokens, comparing digit runs numerically and non-digit runs lexicographically, and handling the digit-priority rule at the first differing character.

Pro tip: Mention that you would use a stable sort (e.g., Python's sorted or Java's Collections.sort) to preserve the original order of equal elements, and discuss how to handle edge cases like leading zeros and very large numbers.

1. Clarify requirements and edge cases

Ask the interviewer to confirm the rules: numeric comparison for digit runs, digit priority at first difference, and lexicographic for non-digits. Discuss edge cases like empty strings, leading zeros, and numbers exceeding integer limits.

2. Design tokenization strategy

Explain that you will split each string into alternating runs of digits and non-digits. This allows comparing corresponding runs between two strings.

3. Implement comparison logic

Iterate through tokens of both strings. For each pair, if both are digits, compare numerically; if both are non-digits, compare lexicographically; if one is digit and the other non-digit, the digit run takes priority (comes first). If all compared tokens are equal, the shorter string comes first.

4. Handle numeric comparison details

For digit runs, strip leading zeros before comparing lengths or values to avoid issues with large numbers. If lengths differ after stripping, the longer one is larger; if equal, compare lexicographically.

5. Test and discuss trade-offs

Walk through examples to verify correctness. Discuss time complexity (O(n log n * m) where m is average token count) and potential optimizations like caching tokenization.

Key Points to Mention

  • Tokenization of strings into digit and non-digit runs
  • Numeric comparison of digit runs, including handling leading zeros and large numbers
  • Digit priority rule at the first differing character
  • Lexicographic comparison for non-digit parts
  • Stability of the sort and its importance
  • Time and space complexity analysis

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

Q2

How should filenames like 'file01.txt' and 'file1.txt' be ordered when their numeric values are equal due to leading zeros, and how would you implement your chosen tie-break?

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

They asked this as a follow-up and I fumbled it a bit.

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AI HintsAI Generated

Suggested Approach

Acknowledge that when numeric values are equal, the tie-break should be defined by the product requirements or user expectations, but a common and predictable choice is lexicographic order of the full filename. Then, describe how to implement a comparator that first compares numeric parts and falls back to lexicographic comparison, ensuring stability and clarity.

Pro tip: Mention that the tie-break should be explicitly documented and tested, as implicit assumptions can lead to bugs and user confusion. Also, consider that different operating systems or file systems may have their own default ordering, so consistency across platforms is key.

1. Clarify the requirement

Ask or state that the tie-break depends on the desired user experience or business logic, but a deterministic and intuitive rule is needed.

2. Choose a tie-break rule

Propose lexicographic ordering of the full filename as a simple, predictable default, or suggest alternative rules like shorter filename first if that better matches expectations.

3. Design the comparator

Outline a comparator that extracts numeric parts, compares them numerically, and if equal, compares the original strings lexicographically.

4. Implement and test

Describe implementation in a language like Python or Java, and emphasize edge cases such as multiple numeric segments and leading zeros.

5. Discuss trade-offs

Mention that lexicographic tie-break may not always be intuitive (e.g., 'file01.txt' before 'file1.txt'), but it is consistent and easy to implement.

Key Points to Mention

  • Natural sort order vs. lexicographic order
  • Comparator design with numeric and string comparison
  • Stability and determinism in sorting
  • Edge cases: multiple numeric parts, leading zeros, different extensions
  • Cross-platform consistency and documentation
  • Testing with unit tests for tie-break scenarios

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

Q3

If you need to sort a very large number of filenames, how would you optimize the approach to avoid repeatedly parsing digit runs inside the comparator?

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

Pre-compute a key for each filename, basically transform each string into a list of typed tokens once upfront, then sort on those.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the problem: sorting filenames with embedded numbers (natural sort) where naive comparators repeatedly parse digit runs, causing O(n log n * k) overhead. Then propose a decorate-sort-undecorate approach: precompute a sort key for each filename that captures the numeric segments, so the comparator only compares precomputed keys. Finally, discuss trade-offs like memory usage and implementation complexity, and mention alternative strategies such as radix sort or bucket sort if the key structure allows.

Pro tip: Mention that you can avoid parsing entirely by using a custom key object that stores the numeric segments as integers, and that Python's sort is stable and uses Timsort, so precomputing keys is both efficient and simple. Also note that if filenames are extremely large in number, external sorting or parallel processing might be necessary.

1. Clarify the problem and constraints

Confirm that the filenames contain digit runs that need natural sorting, and discuss the scale (e.g., millions of files) and memory limitations. This ensures the solution fits the context.

2. Identify the inefficiency

Explain that a naive comparator parses digit runs on every comparison, leading to repeated work and poor performance. Quantify the overhead: O(n log n) comparisons, each potentially parsing multiple digit runs.

3. Propose key precomputation (decorate-sort-undecorate)

Describe how to precompute a sort key for each filename once, storing numeric segments as integers and non-numeric parts as strings. Then sort using these keys, so comparisons are fast and parsing happens only once per filename.

4. Discuss implementation details and trade-offs

Mention how to handle leading zeros, negative numbers, or mixed types. Compare memory overhead of storing keys versus repeated parsing, and note that the approach is O(n) preprocessing + O(n log n) comparisons with cheap key comparisons.

5. Consider alternatives and optimizations

If memory is tight, suggest on-the-fly parsing with caching, or if keys are simple, use radix sort or bucket sort. Also mention parallel sorting or external sorting for extremely large datasets.

Key Points to Mention

  • Natural sort order and the need to compare numeric segments as numbers, not strings.
  • Decorate-sort-undecorate (Schwartzian transform) to precompute keys.
  • Time complexity: O(n) preprocessing + O(n log n) comparisons with O(1) key comparisons.
  • Memory trade-off: storing keys increases memory usage but drastically reduces CPU time.
  • Handling edge cases: leading zeros, negative numbers, and non-numeric prefixes.
  • Alternative algorithms: radix sort, bucket sort, or external sorting for huge datasets.

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