The Interview Loop, Stage by Stage

Cursor is hiring an IT Systems Engineer to treat IT as software engineering, so the loop is built to find out whether you reach for code by default and can own systems with almost no management around you. Hold the whole shape in your head before you prep a single answer.

Most of what is publicly verified comes from Cursor's SWE loop: a short recruiter or hiring-manager screen, one to three 60-minute technical screens, then a paid onsite project that is often eight hours and sometimes runs one to two days. That onsite is the real decision round, not a formality at the end.

What that practical round looks like for an IT/Systems hire is an inference, drawn from how Cursor runs SWE onsites and how senior IT loops run across the industry. The honest read: expect a hands-on build, troubleshoot or runbook rather than the SWE coding project. Flag it as inference when you talk to your recruiter and let what they describe override this map.

1. 1Recruiter / hiring-manager screen (~30-45 min). Informal conversation with the Head of IT or a recruiter on background, why-Cursor and a read on whether IT is engineering for you.
2. 2Technical screen #1 (~60 min). A hands-on scripting problem in Python or Bash plus deep configuration-level questions on SAMLAn enterprise standard that powers single sign-on., OIDCOpenID Connect. A modern standard that powers single sign-on, built on OAuth./OAuth, SCIMSystem for Cross-domain Identity Management. A standard for automatically creating and removing user accounts when people join or leave. and MDM.
3. 3Technical screen #2 (~60 min). A systems-design / scenario round: design an automated JML pipeline or a zero-trust access model end-to-end, with trade-offs.
4. 4Practical / work-trial round. Cursor's signature paid onsite, reframed for IT as a real build, automation or live troubleshoot rather than abstract whiteboarding (general-industry inference).
5. 5Cross-functional / values conversations. Sessions with Security, Engineering and potential teammates on collaboration, ownership and how you operate on a flat team.
6. 6Founder / Head of IT final. A closer plus references and the implicit AI-native check: do you actually use Cursor and AI tooling in your own daily work.

Thirty to forty-five minutes, informal, often with the Head of IT directly because the team is small. Light on technical depth, heavy on one question: is IT engineering for you or is it ticket-closing?

The screener is sorting for three things and a generic answer dies on any of them. They want to hear that you instinctively script away toil, that you have a specific reason for Cursor rather than "I like AI," and that you can operate with very little oversight on a flat team.

Have one story loaded and ready: a system you owned end-to-end and automated. Ninety seconds, with a number that lands.

• Open with the manual pain: "Onboarding took our team three hours per hire across eight SaaS apps, all by hand."
• Name what you built: an HRIS-triggered JML pipeline that provisioned accounts and groups via SCIMSystem for Cross-domain Identity Management. A standard for automatically creating and removing user accounts when people join or leave. and the Okta API.
• Land the outcome with a metric: "Onboarding dropped to under five minutes, fully audited and offboarding became same-day."
• Close on ownership: you designed it, you shipped it, you ran it in production and on call for it.

Bring your own questions

• How big is the IT team today and what's the charter - pure internal IT or shared with Security?
• What's the current stack: IdP, MDM, HRIS, SaaS portfolio?
• What does the M&A integration roadmap look like - how often does Cursor acquire and absorb companies?
• What does success look like in the first 90 days for this hire?

Sixty minutes that split in two: a live scripting problem and deep, configuration-level questions on identity. Both are graded as a senior engineer, which means trade-offs and failure modes, not textbook definitions.

The scripting half is usually realistic IT automation, not algorithm puzzles. Expect to call a REST API to reconcile users between systems, parse a log to find an anomaly or script a provisioning step. They watch how you write it: idempotent, error-handled and safe to re-run.

import os, requests

BASE = "https://your-org.okta.com/api/v1"
HEADERS = {"Authorization": f"SSWS {os.environ['OKTA_TOKEN']}"}

def get_all_users():
    """Page through every active user, following Okta's Link header."""
    users, url = [], f"{BASE}/users?filter=status eq \"ACTIVE\"&limit=200"
    while url:
        r = requests.get(url, headers=HEADERS, timeout=30)
        r.raise_for_status()
        users.extend(r.json())
        url = r.links.get("next", {}).get("url")  # pagination, not a magic page count
    return users

def ensure_in_group(user_id, group_id):
    """Idempotent: PUT is safe to re-run; adding an existing member is a no-op."""
    r = requests.put(f"{BASE}/groups/{group_id}/users/{user_id}",
                     headers=HEADERS, timeout=30)
    r.raise_for_status()

Narrate the choices as you go. Mention pagination so you don't silently drop users past page one, rate-limit handling for 429s, secrets pulled from the environment not hardcoded and the fact that re-running the script can't double-provision anyone.

The identity half: debug, don't define

They won't ask "what is SAMLAn enterprise standard that powers single sign-on.." They'll ask how you'd debug a specific failure. Have crisp answers for the common breakages across the three protocols you'll live in.

An open-ended design round, usually one of two prompts: design an automated joiner/mover/leaver pipeline or design a zero-trust access model. There's no single right answer, so they grade your structure, your trade-offs and whether you think past the happy path.

Use this stage map to decide what evidence belongs in each round. Memorizing the order is the shallow version. For every stage, prepare one artifact, one story and one question that shows how you reason in the role.

Run the same skeleton every time. It keeps you from rambling and signals that you've designed real systems, not just operated them.

1. 1Clarify requirements. How many employees, how fast is headcount growing, which platforms and SaaS apps, what compliance regime (SOC 2 / ISO 27001)?
2. 2Name the source of truth. For JML it's the HRIS - every join, move and leave originates there, never from manual tickets.
3. 3Map the data flow. HRIS event → IdP (Okta) → group membership (RBACRole-Based Access Control. Granting permissions by role rather than configuring each person individually./ABAC) → downstream apps via SCIMSystem for Cross-domain Identity Management. A standard for automatically creating and removing user accounts when people join or leave./API → MDM for device state.
4. 4Walk failure and edge cases. Partial provisioning, API outages, drift between IdP and apps, a rehire, a contractor-to-FTE conversion.
5. 5Cover security and audit. Least privilege, access reviews, immutable logs, evidence for auditors, secrets management.
6. 6Show how it scales. Idempotent reconciliation jobs, policy-as-code, dynamic groups so new apps and new hires don't mean new manual steps.

The detail that separates senior from mid-level is what you say about the unglamorous parts. Anyone can draw the happy path.

Name tools, justify with trade-offs

This is the block that decides it. Cursor's signature is a paid, real-project onsite - for SWE it's an ~8-hour build, sometimes one to two days. The IT equivalent is most likely a hands-on build, automation or live troubleshoot, not a quiz (general-industry inference, confirm with your recruiter).

The format mirrors day-one work on purpose: a real problem, limited docs and a few hours to show how you operate under ambiguity. They're not grading a perfect answer. They're watching your working style.

1. 1Scope fast. Spend the first ten minutes pinning down what "done" means and the smallest version that's genuinely useful. Say your scope out loud and check it.
2. 2Build something that runs. Get a working slice end-to-end early, then deepen - a script that provisions one app beats a beautiful design that does nothing.
3. 3Narrate trade-offs. As you go, say what you're choosing and what you're deferring, so they see the judgment behind the code.
4. 4Leave it documented. A short README or runbook with assumptions, how to run it and what you'd do next signals you build for the team, not just for the demo.

• Bring an opinionated approach - flat-team culture rewards agency, not waiting for direction or asking permission for every decision.
• When you hit an unknown, state your assumption and move; don't freeze waiting for the interviewer to unblock you.
• If you finish the core early, harden it: add error handling, an idempotency guard or a test - that's what a senior would do with spare time.
• Demo it like you'd demo to a teammate: here's the problem, here's what runs, here's the trade-off I made and why.

The technical rounds prove you can do the work. These rounds decide whether Cursor wants you doing it next to them. Expect conversations with Security, Engineering, potential teammates and a final with the Head of IT or a founder.

There's an implicit AI-authenticity test running under all of it. The people interviewing you build an AI code editor and use it constantly, so they can tell within minutes whether you genuinely use AI/Cursor daily. Vague claims collapse under one follow-up. Have real, specific anecdotes.

The founder / Head of IT final

This closer rewards conviction. Be ready to defend an opinion under pushback without getting brittle and to show pragmatism over process - Cursor prizes shipping over ceremony. Hold your view, but update visibly if they raise a point you hadn't weighed.