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Enterprise Solutions Engineer - Central

Oak Street Health · Chicago, IL · 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 deal you helped win where the technical work made the difference.

What they are checking: Whether they have truly been the technical backbone of a sale, not just a demo giver.

How do you split responsibilities with an Account Executive during a deal?

What they are checking: Whether they work as a real partner to sales and know where their role starts and stops.

This is an early-stage company. Tell me about a time you worked without clear process or documentation.

What they are checking: Whether they can create structure themselves in a startup that is just getting started.

What would you do

A prospect's security team says they already have SailPoint and Okta and don't need another tool. How do you respond?

What they are checking: Whether they can position a new platform against tools the buyer already owns without bashing competitors.

A demo breaks in front of a prospect. What do you do?

What they are checking: Whether they stay calm and keep credibility when something goes wrong live.

What feedback would you bring back to the product team after a few months in the field?

What they are checking: Whether they see the field role as a source of product insight, not just a sales function.

About the work

Explain identity governance and administration to me as if I'm a CISO who's heard every vendor pitch.

What they are checking: Whether they can speak credibly about IGA to a skeptical senior buyer without sounding like marketing.

Why are machine identities and AI agents harder to govern than human users?

What they are checking: Whether they understand the problem behind the product, which is central to how it is sold.

Walk me through how you'd run a proof of value with a large enterprise prospect.

What they are checking: Whether they can scope success criteria, manage the timeline and actually prove the value to a buyer.

How do you connect an identity platform to an application that has no standard connector or SCIM support?

What they are checking: Whether they understand integration realities that decide whether a deal succeeds.

How would you answer a buyer who asks how the AI agents make access decisions and how they can trust them?

What they are checking: Whether they can address explainability and control concerns about AI in security honestly.

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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)

Apply at Oak Street Health