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Enterprise Solutions Engineer - West

Oak Street Health · San Francisco · 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 demo that went wrong in front of a customer. How did you recover?

What they are checking: Whether they stay composed and keep credibility when technology fails in front of a buyer.

How do you split responsibilities with an account executive on a large deal?

What they are checking: Whether they understand their role as the technical backbone and partner well on shared deals.

Tell me about feedback from customers that you brought back to a product team. What happened with it?

What they are checking: Whether they help shape the product at an early-stage company by passing along clear, useful field insight.

What would you do

A customer's security architect challenges how an AI agent can be trusted to make access decisions. How do you answer?

What they are checking: Whether they can address real concerns about AI in security honestly, without overselling.

How would you show a customer the value of a live identity graph compared to the periodic access reviews they run today?

What they are checking: Whether they can tie a technical feature to a business outcome a security leader cares about.

How do you handle a customer asking for a feature that doesn't exist yet in the middle of a POV?

What they are checking: Whether they can stay honest about gaps while keeping the deal moving.

About the work

Walk me through how you'd run a proof of value for an identity platform at a large enterprise.

What they are checking: Whether they can scope success criteria, connect real systems and prove value in a short, controlled window.

How would you explain the difference between identity governance, access management and privileged access to a non-technical buyer?

What they are checking: Whether they know the IAM landscape well and can make it simple for any audience.

Oak uses a connector framework to reach any application. What questions would you ask a customer about their apps before a POV?

What they are checking: Whether they think ahead about integration risks like custom apps, APIs and permissions that sink technical evaluations.

What identity systems have you worked with hands-on, like Okta, Entra ID, SailPoint or CyberArk?

What they are checking: Whether they have real hands-on depth that will hold up in front of technical security buyers.

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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