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Enterprise Solutions Engineer - East

Oak Street Health · NY · Remote available · Full time · Solutions

Posted Jul 15, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you won over a skeptical technical evaluator.

What they are checking: Whether they earn credibility through honesty and depth rather than pressure.

Tell me about a time a demo or POV broke in front of a customer. What did you do?

What they are checking: Whether they stay calm and keep trust when something fails during a live evaluation.

How do you keep your technical skills current when the AI and identity space changes so fast?

What they are checking: Whether they actively keep learning, which matters at a startup building in a fast-moving category.

What would you do

An auditor-driven buyer cares most about proving who had access to what last quarter. How would you shape the demo for them?

What they are checking: Whether they can tailor a demo to a buyer's real driver, such as compliance, instead of showing every feature.

How do you work with an account executive when you think a deal isn't technically a good fit?

What they are checking: Whether they will raise fit concerns early, protecting the company from bad deals and failed rollouts.

A customer asks how Oak handles least privilege and access reviews compared to their current tools. How do you answer without trashing a competitor?

What they are checking: Whether they can compare products fairly and keep the focus on the customer's problem.

About the work

Walk me through how you'd run a proof of value for an identity platform at a large East Coast financial firm.

What they are checking: Whether they can scope success criteria and run a technical evaluation in a regulated, security-heavy environment.

How do you explain the problem of machine identities and AI agents to a security team that only manages human users today?

What they are checking: Whether they understand the shift the posting describes and can help buyers see risks they are missing.

What would you need to know about a customer's environment before connecting Oak to their applications?

What they are checking: Whether they anticipate integration issues like custom apps, API limits and permissions before they derail a POV.

Which identity tools have you configured yourself, and what did you learn from them?

What they are checking: Whether their IAM knowledge is hands-on enough to hold up with senior security engineers.

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The full job description

As published by Oak Street Health.

We're reimagining enterprise Identity and Access Management from the ground up. Founded by serial entrepreneurs Shai Morag and Tal Marom and backed by a $60M seed round from Greylock, Accel, and CRV, we're building the next generation of identity security. Identity is the gateway to everything- who's let in, who's kept out, and it's now the number one attack vector in the enterprise. The tools built to govern it were designed for a slower world of human users and static environments. That world is gone. Identities are exploding across human, machine, and AI agents faster than legacy systems can track, and security teams are left patching together five disconnected tools that still can't answer "who has access to what, right now." We think the answer isn't another point solution- it's a new foundation. Oak is the AI-native Identity Operating System: an AI connector framework that reaches any application, a live identity graph built from raw evidence, and a team of AI agents that governs the full lifecycle of every identity in one platform. We're building Oak's AI-native core from day one-engineered for what enterprise identity is becoming, not patched onto what it used to be. And we're just getting started. About the Role: As a Solutions Engineer at Oak, you'll be the technical backbone of our sales motion - partnering with Account Executives to prove Oak's value in front of CISOs, IAM engineers, and compliance leaders at some of the most complex enterprises in the market. You'll own the technical narrative from first discovery call through POV, showing prospects how Oak's identity graph and infinite-connector data lake bring visibility across their on-prem, cloud, SaaS, and homegrown apps. This is a hands-on, high-leverage role: you'll be running demos, standing up proofs of value, and answering the hard technical questions that separate a real platform from a slide deck. You'll work closely with Solutions leadership to shape how Oak's IGA augmentation and autonomous replacement story lands technically across every stage of the pipeline. What you will do: • Run technical discovery calls to uncover a prospect's identity stack, including on-prem, cloud, SaaS, and homegrown app coverage gaps • Deliver tailored, high-impact product demos showing how Oak's identity graph unifies access reviews, JIT requests, and lifecycle management for humans, NHIs, and AI agents • Design and execute Proofs of Value (POVs) with prospects • Own technical responses to RFPs/RFIs and security questionnaires • Partner with Account Executives to build the technical strategy for each opportunity and troubleshoot deal blockers • Feed prospect and customer technical feedback back to Product and Engineering to sharpen Oak's roadmap What you will bring : • 7+ years od experience as a Solutions Engineer / Sales Engineer at a cybersecurity or identity company (IAM, IGA, PAM, or adjacent) • Working knowledge of IAM/IGA concepts - JML, access reviews, RBAC/ABAC, SoD, SCIM, SAML/OAuth • Comfort running live technical demos and POVs in front of technical and executive audiences • Ability to translate complex technical concepts into business risk and ROI for CISOs and compliance stakeholders • Strong ownership mentality - comfortable operating with autonomy in a fast-moving startup environment • Excellent written and verbal communication skills, including RFP/security questionnaire responses Nice to have: • Hands-on experience with identity governance platforms • Familiarity with Non-Human Identity (NHI) or AI agent governance use cases • Scripting or API integration experience (Python, REST APIs)

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