Interview guides · Hillwood

Hillwood Software Engineer Interview Guide

Hillwood Software Engineer interview guide: reported rounds, questions and how candidates describe the process.

The 60-second brief

At Hillwood, the Software Engineer role is pivotal to building the digital infrastructure that supports complex, large-scale industrial and commercial real estate operations. You will not just be writing code; you will be contributing to the technical backbone that enables Hillwood to maintain its competitive edge in a fast-paced market. Your work will directly impact how the organization manages data, optimizes construction projects, and streamlines cross-functional workflows. This position demands a unique blend of technical proficiency and business acumen. You will be expected to translate high-level project requirements into robust, scalable software solutions. Because Hillwood operates at the intersection of technology and physical development, you will find yourself collaborating with stakeholders who rely on your systems to drive real-world impact.

This guide is scoped to a Software Engineer candidate at Hillwood.

Focus areas

Software Engineering (General)
Interview Process Communication
Problem Solving

The Hillwood interview process

Hillwood candidates report 4 rounds over 3-5 weeks. The stages below are what candidates describe, not a published process.

Initial Screening

The process begins with an initial screening to assess your technical depth and fit for the team.

What to demonstrate

The process begins with an initial screening to assess your technical depth and fit for the team
Depth in Software Engineering (General)

How to prepare

Be able to walk your CV end to end in two minutes, and say why this company specifically.
Have your salary expectations, notice period and location constraints ready, and ask for the rest of the loop in writing.

Technical Screenings

You will undergo multiple technical screenings to evaluate your coding skills and system design capabilities.

What to demonstrate

You will undergo multiple technical screenings to evaluate your coding skills and system design capabilities
Depth in Software Engineering (General)

How to prepare

Answer aloud and timed: Describe your process for handling technical debt in a long-term project.
Answer aloud and timed: How do you ensure your code is maintainable and well-documented for future team members?

Deep-Dive Discussions

Engage in deep-dive discussions with various team members to ensure alignment and assess collaboration skills.

What to demonstrate

Engage in deep-dive discussions with various team members to ensure alignment and assess collaboration skills
Depth in Software Engineering (General)

How to prepare

Answer aloud and timed: Tell me about a time you had to work with a stakeholder who had conflicting project priorities.
Answer aloud and timed: How do you handle situations where the project requirements are ambiguous or changing?

Final Round Interviews

Participate in final round interviews that may include behavioral assessments and technical evaluations.

What to demonstrate

Participate in final round interviews that may include behavioral assessments and technical evaluations
Depth in Software Engineering (General)

How to prepare

Answer aloud and timed: Describe a time you had to advocate for a technical decision to a non-technical manager.
Answer aloud and timed: What motivates you to work within the real estate and construction technology space?

Where candidates lose points

Show your work

When answering technical questions, talk through your thought process out loud. We want to see how you approach a problem, not just the final result.

Be proactive in follow-ups

If you haven't heard back, it is acceptable to send a polite, professional follow-up email after a reasonable amount of time.

Research the industry

Understanding the challenges inherent in the construction and real estate sectors will give you a significant advantage in your behavioral interviews.

Prepare for ambiguity

Real-world engineering rarely involves perfectly defined requirements; demonstrate how you handle uncertainty and iterate toward a solution.

Questions & practice

Identify the heaviest tenants in a five-minute window under memory pressure

Medium · top-k · heavy hitters · streaming

The edge service handles about 3,000 requests per second across roughly 50,000 tenants, peaking near 9,000. Expose the 50 heaviest tenants by request count over the trailing five minutes so limits can be tightened before one tenant's backfill starves the fleet. You may not retain five minutes of raw records. Give the exact solution and its memory, then the bounded-memory approximation with its error stated as a formula, and say which you would ship and at what tenant cardinality that choice changes.

Approach

Do the exact version first, because it is affordable at this cardinality: a ring of 300 one-second counters per tenant, advanced lazily, is 1,200 bytes of counters per tenant and roughly 60 to 90 MB for 50,000 tenants with overhead. Carry a running total and subtract the bucket you overwrite so a window read is O(1) rather than 300 adds.
Extract the top 50 with a size-k min-heap over the tenant sums: O(d log k) for d tenants, against O(d log d) to sort them all. Maintaining the heap continuously instead of on query requires a tenant-to-heap-index map, because incrementing a count already inside the heap means sifting from a known position, and without that map you rebuild the heap on every request.
State the approximation precisely rather than gesturing at sketches. Misra-Gries with m counters retains every item whose true count exceeds N/(m+1), and each retained count underestimates the truth by at most N/(m+1). With m = 1,000 and N = 900,000 requests in the window the error is roughly 900 requests, which is fine for spotting a tenant sending 50,000 and useless for ranking two tenants 200 apart.
Say what breaks when the window slides: Misra-Gries and Space-Saving are insert-only and cannot be decremented as records age out. The workable construction is one summary per sub-window, say ten seconds, with 30 summaries merged at query time, and the merged error is the sum of the per-summary errors, so the bound degrades linearly in the number of sub-windows.

Follow-up

The heaviest tenant is heavy because of one export job rather than user traffic. Should the limiter treat those as the same tenant?
Two tenants sit tied at the boundary of the top 50. Does your answer flap, and does the flapping matter?

Find overlapping job attempts and peak concurrency from lease records

Medium · sweep line · intervals · leases

A day of job_run history yields about 50,000,000 attempt records: (job_run_id, job_type, attempt, started_at, finished_at which is NULL when the worker died, lease_expires_at). Leases expire on a clock, so a job that outran its lease ran twice. Produce (a) every job_run_id whose attempts overlapped in wall-clock time and (b) the peak number of simultaneously running attempts per job_type with the minute it occurred. Target O(n log n). State how you treat a NULL finished_at and what clock skew does to your answer.

Approach

Define the interval before sorting anything: an attempt occupies [started_at, COALESCE(finished_at, lease_expires_at)). finished_at is observed and lease_expires_at is only a promise, so every attempt without a finish contributes an estimate and the whole result is a lower bound on overlap rather than an exact count.
For peak concurrency, sweep: emit 2n endpoints, sort by (timestamp, kind) with ends ordered before starts at equal timestamps, then walk the sequence maintaining a counter per job_type and record each type's maximum with its timestamp. O(n log n) dominated by the sort, O(n) space, or O(1) extra if the sort is external and the walk streams.
For overlap detection, do not compare attempts pairwise. A single global sort by (job_run_id, started_at) gives both the grouping and the order; within a group, keep the maximum end seen so far and report an overlap exactly when the next start is less than that running maximum, which is one linear pass after the sort.
Half-open intervals matter and are easy to get wrong: with closed intervals an attempt ending at the same millisecond another begins reads as concurrency two, and across 50,000,000 records that artefact swamps the real signal.

Follow-up

A handler is not idempotent and you have found 400 overlapping jobs. Which of them actually caused damage, and what would you query to find out?
Peak concurrency for one job_type is 4 against a configured cap of 4. Is the cap working, or is the data hiding attempts that never started?

Collapse a redelivered event batch into per-aggregate high-water marks

Easy · hashing · at-least-once · aggregation

You drain a batch of up to 5,000,000 events, each (aggregate_id BIGINT, aggregate_version INT, event_type, payload). The log guarantees order within one aggregate only; the batch merges 64 partitions, and a relay failover has redelivered a range, so an older version for an aggregate can appear after a newer one. Given a map of last_applied_version per aggregate, produce the events worth applying, at most one per (aggregate_id, version), plus the count discarded. Target O(n) time. State the memory for 2,000,000 distinct aggregates and what you do when it does not fit.

Approach

One pass, one hash map from aggregate_id to the highest version kept, and a discard counter. An event whose version is at or below last_applied_version for its aggregate is dropped without further work, which is the whole reason the event carries its version rather than a delta. O(n) expected time, O(d) space in distinct aggregates.
Keep the maximum, never the last occurrence. The redelivered range means the final appearance of an aggregate in the batch can be an older version than one seen earlier in the same batch, so last-wins applies stale state over newer state and the projection regresses with no error anywhere.
Cost the memory instead of calling it large: an 8-byte key plus a 4-byte version is 12 bytes of payload, and an open-addressed table held at a 0.7 load factor costs roughly 17 bytes per entry before per-slot metadata, so 2,000,000 aggregates is tens of megabytes in a native layout and several times that in a runtime that boxes both key and value.
If the distinct set exceeds memory, partition on hash(aggregate_id) mod P and reduce each partition independently. Every event for one aggregate hashes to the same partition, so the per-partition result is exact and the merge is concatenation rather than a second reduction.

Follow-up

The payload is a patch rather than a snapshot, so applying only the highest version loses the intermediate changes. What changes in your reduction?
How do you detect that version 7 arrived while version 6 was never delivered, and what should the consumer do about the gap?

Hold a per-tenant active cap against concurrent creates

Hard · write skew · isolation levels · constraints

A tenant on the standard plan may hold at most 50 resources with status='active'. The create handler runs SELECT count(*) FROM resource WHERE tenant_id = $1 AND status = 'active', compares to 50, then inserts. Two creates arrive 3 ms apart on different instances and the tenant lands at 51. Name the anomaly, say whether PostgreSQL 16 READ COMMITTED or REPEATABLE READ prevents it and why, then give an implementation that holds the cap at READ COMMITTED with the exact statements. Finally, say what changes when the cap is 'at most one running export per tenant' on job_run.

Approach

Name it: write skew. The two transactions read an overlapping set and write disjoint rows, so there is no row-level conflict for the engine to detect and each commit is individually legal.
Rule out the levels precisely. READ COMMITTED takes a fresh snapshot per statement and takes no lock on the counted rows, so both see 49. PostgreSQL's REPEATABLE READ is snapshot isolation: it removes non-repeatable reads and phantoms within the snapshot but still admits write skew, because the anomaly is not a re-read of a changed row, it is a read of a set that a concurrent transaction invalidates. Only SERIALIZABLE closes it, by tracking the read dependency and aborting one transaction with SQLSTATE 40001 — a guarantee that exists only if the application re-runs the whole transaction from the read.
Convert the set predicate into a single-row conflict: keep tenant.active_resource_count and run UPDATE tenant SET active_resource_count = active_resource_count + 1 WHERE tenant_id = $1 AND active_resource_count < 50 in the same transaction as the INSERT. Zero affected rows is the cap, returned as 409. The row lock serialises the decision at any isolation level, and contention is bounded to one tenant's row — which is also the fair-scheduling unit, unlike a global counter that would convoy every tenant behind one row.
State the cost you just took on: a counter is a second source of truth that can drift, so every path that changes status must adjust it inside the same transaction, and a periodic reconciliation has to exist, with resource_revision as the authority for what the count should have been.

Follow-up

A resource moves from archived back to active. Which statements change, and what breaks if the counter update and the status change land in different transactions?
The cap becomes plan-dependent and a plan can change mid-month. Where does the number 50 live, and who reads it?

Find version gaps and relay lag with window functions

Medium · window functions · event tables · frame semantics

outbox_event holds event_id, aggregate_type, aggregate_id, aggregate_version, event_type, payload, status ('pending','published','dead'), attempts, created_at, published_at. A projection is missing rows and you must decide whether the relay skipped events or the consumer dropped them. Write three queries over the last seven days: one listing every aggregate_id whose published aggregate_version sequence has a hole, one giving per-day counts with a running total, and one returning the newest published event per aggregate. For each, say where the window function is evaluated relative to WHERE and LIMIT. PostgreSQL 16.

Approach

Gaps: compute lead(aggregate_version) OVER (PARTITION BY aggregate_id ORDER BY aggregate_version) in a subquery, then filter next_version <> aggregate_version + 1 in the outer query. Window functions are evaluated after WHERE, GROUP BY and HAVING and before the outer ORDER BY and LIMIT, so the predicate cannot sit in the same WHERE clause and PostgreSQL 16 has no QUALIFY.
Say what the seven-day filter does to the answer: it truncates every partition, so the first row per aggregate has no predecessor inside the window and a hole spanning the boundary is invisible. Widen the window, or join to resource.version as the authority for the true maximum.
Running total: SELECT date_trunc('day', created_at) AS d, count() AS n, sum(count()) OVER (ORDER BY date_trunc('day', created_at) ROWS UNBOUNDED PRECEDING). An aggregate inside a window call is legal because grouping runs before windowing. The grouping key is unique per row here so ROWS and RANGE agree, but write the frame anyway — over ungrouped rows with tied timestamps the default RANGE frame pulls in every peer row and the total jumps.
Newest per aggregate: DISTINCT ON (aggregate_id) ... ORDER BY aggregate_id, aggregate_version DESC is the cheap PostgreSQL-only form when an index matches that order; row_number() OVER (PARTITION BY aggregate_id ORDER BY aggregate_version DESC) = 1 is the portable form and needs a subquery for the same evaluation-order reason as the gap query.

Follow-up

Relay failover redelivers events. Does a duplicate break the gap query, and how would you detect one from this table alone?
Turn the gap check into a continuous monitor rather than a query someone runs after an incident. What does it watch?

How do you approach designing a scalable system for managing project data?

Medium · Technical Competency and System Design

Approach

Fix the scope first: who calls this, how often, and what they do when it fails.
Name the read and write paths separately; they rarely have the same bottleneck.
Choose a partition key and say what query it makes expensive.
State the consistency you need, and where you are willing to be stale.

Follow-up

What breaks first when traffic grows ten times?
How does this behave when that dependency is down for an hour?

Can you explain a time you had to refactor a complex piece of code to improve performance?

Medium · Technical Competency and System Design

Approach

Fix the scope first: who calls this, how often, and what they do when it fails.
Name the read and write paths separately; they rarely have the same bottleneck.
Choose a partition key and say what query it makes expensive.
State the consistency you need, and where you are willing to be stale.

Follow-up

What breaks first when traffic grows ten times?
How does this behave when that dependency is down for an hour?

Describe your process for handling technical debt in a long-term project.

Medium · Technical Competency and System Design

Approach

Fix the scope first: who calls this, how often, and what they do when it fails.
Name the read and write paths separately; they rarely have the same bottleneck.
Choose a partition key and say what query it makes expensive.
State the consistency you need, and where you are willing to be stale.

Follow-up

What breaks first when traffic grows ten times?
How does this behave when that dependency is down for an hour?

How do you ensure your code is maintainable and well-documented for future team members?

Medium · Technical Competency and System Design

Approach

Fix the scope first: who calls this, how often, and what they do when it fails.
Name the read and write paths separately; they rarely have the same bottleneck.
Choose a partition key and say what query it makes expensive.
State the consistency you need, and where you are willing to be stale.

Follow-up

What breaks first when traffic grows ten times?
How does this behave when that dependency is down for an hour?

Listing latency scales with page size, not with filters

Easy · n+1 · latency · query batching

The tenant listing endpoint reads resource filtered by tenant_id and status, ordered by updated_at DESC, and returns each row plus the owner's display name from app_user and the actor of that resource's latest resource_revision. p99 is 55 ms at 10 rows per page and 1.4 s at 200. Database telemetry shows 401 statements per request, each under 1 ms, and nothing in the slow-query log. Diagnose the cause and give the fix, stating the statement count per request and the p99 you expect afterwards.

Approach

Read the counters before forming a theory. 401 statements for 200 rows is one driver query plus two per row, and sub-millisecond execution with an empty slow-query log rules out a bad plan. The time is round trips, which is why it is invisible in every per-query metric and scales with rows returned rather than with filter selectivity.
Name the two per-row statements from their normalised text: a single-row app_user lookup by user_id, and a resource_revision lookup by resource_id ordered by version DESC LIMIT 1. Confirm by dropping those two response fields and watching the statement count fall to one. That locates the calls in the serialisation layer, not the repository.
Check that the arithmetic accounts for the whole gap. Measure one round trip to the replica in isolation; 400 trips at roughly 3 ms of network plus 0.2 ms of execution is about 1.3 s on top of a 55 ms baseline, which matches. If the multiplication had fallen short, the N+1 would only be part of the story and you would keep looking.
Batch both lookups. Collect owner_user_ids and resource_ids from the driver query, then issue WHERE tenant_id = $1 AND user_id = ANY($2) for the users, and PostgreSQL's SELECT DISTINCT ON (resource_id) ... WHERE resource_id = ANY($2) ORDER BY resource_id, version DESC for the latest revision, which the UNIQUE (resource_id, version) index serves directly. On an engine without DISTINCT ON, use a lateral join or a row_number window. Three statements per request at any page size.

Follow-up

The page size is capped at 200 today. What breaks first if it is raised to 2,000, and is it still this bug?
How do you stop the next N+1 from reaching production, given that no individual query is slow and the endpoint's tests pass?

Suggested practice checklist

Built from the rounds and topics Hillwood candidates report.

Day 1 — Map the Hillwood loop

Write out the reported sequence: Initial Screening, Technical Screenings, Deep-Dive Discussions, Final Round Interviews.
For each round, write one sentence on what it is judging, from the description above, and mark the one you are least ready for.

Deliverable: A one-page map of the 4 reported rounds, with the weakest marked.

Day 2 — Work Software Engineering (General)

Spend the session on Software Engineering (General), which Hillwood candidates report being tested on.
Write one worked example in Software Engineering (General) and time yourself on it.

Deliverable: One timed worked example in Software Engineering (General).

Day 3 — Work Interview Process Communication

Spend the session on Interview Process Communication, which Hillwood candidates report being tested on.
Write one worked example in Interview Process Communication and time yourself on it.

Deliverable: One timed worked example in Interview Process Communication.

Day 4 — Work Problem Solving

Spend the session on Problem Solving, which Hillwood candidates report being tested on.
Write one worked example in Problem Solving and time yourself on it.

Deliverable: One timed worked example in Problem Solving.

Day 5 — Answer out loud: Technical Competency and System Design

Answer aloud, timed: How do you approach designing a scalable system for managing project data?
Answer aloud, timed: Can you explain a time you had to refactor a complex piece of code to improve performance?

Deliverable: Spoken answers to 2 reported Technical Competency and System Design question(s), under time.

Day 6 — Answer out loud: Behavioral and Cultural Alignment

Answer aloud, timed: Tell me about a time you had to work with a stakeholder who had conflicting project priorities.
Answer aloud, timed: How do you handle situations where the project requirements are ambiguous or changing?

Deliverable: Spoken answers to 2 reported Behavioral and Cultural Alignment question(s), under time.

Day 7 — Dry run for Hillwood

Run one full mock under time, then write down the two questions you most want to ask your interviewers.

Deliverable: A completed timed mock and two questions to ask.

Behavioural preparation

Behavioural rounds judge the decision you made and what it cost.

Tell me about a time you had to work with a stakeholder who had conflicting project priorities.

Medium · Behavioral and Cultural Alignment

Approach

Pick a story where you made the decision, not one where you watched it.
State the situation in two sentences and spend the rest on the reasoning.
Give the blast radius: what could have broken, and what you measured.
Name the disagreement and how you resolved it with evidence.

Follow-up

What would you do differently if you ran that again?
How did you know your change caused the improvement?

How do you handle situations where the project requirements are ambiguous or changing?

Medium · Behavioral and Cultural Alignment

Approach

Pick a story where you made the decision, not one where you watched it.
State the situation in two sentences and spend the rest on the reasoning.
Give the blast radius: what could have broken, and what you measured.
Name the disagreement and how you resolved it with evidence.

Follow-up

What would you do differently if you ran that again?
How did you know your change caused the improvement?

Describe a time you had to advocate for a technical decision to a non-technical manager.

Medium · Behavioral and Cultural Alignment

Approach

Pick a story where you made the decision, not one where you watched it.
State the situation in two sentences and spend the rest on the reasoning.
Give the blast radius: what could have broken, and what you measured.
Name the disagreement and how you resolved it with evidence.

Follow-up

What would you do differently if you ran that again?
How did you know your change caused the improvement?

What motivates you to work within the real estate and construction technology space?

Medium · Behavioral and Cultural Alignment

Approach

Pick a story where you made the decision, not one where you watched it.
State the situation in two sentences and spend the rest on the reasoning.
Give the blast radius: what could have broken, and what you measured.
Name the disagreement and how you resolved it with evidence.

Follow-up

What would you do differently if you ran that again?
How did you know your change caused the improvement?