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Enterprise Account Executive - East Coast

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

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

Walk me through a complex enterprise deal you owned from first cold outreach to close.

What they are checking: Whether they have truly run the full cycle themselves, which the posting says this role owns end to end.

Tell me about a time you built pipeline from nothing in a new territory.

What they are checking: Whether they can self-generate opportunities at an early-stage company with no installed base to lean on.

How do you work with a solutions engineer to plan a high-stakes demo?

What they are checking: Whether they partner well with technical teammates and tailor demos to the buyer's real problems.

Tell me about a negotiation where procurement pushed hard on price late in the deal. What did you do?

What they are checking: Whether they protect deal value and keep momentum without caving or losing the deal.

Why do you want to sell at an early-stage company instead of an established IAM vendor?

What they are checking: Whether they understand the ambiguity and building that early-stage selling demands and actually want it.

What would you do

How would you explain Oak's idea of an AI-native identity operating system to a CISO who already has five identity tools?

What they are checking: Whether they can sell a new category against an existing stack without sounding like another point solution.

Machine identities and AI agents are growing faster than human users. How would you use that in a conversation with a buyer?

What they are checking: Whether they can turn a market shift into a reason a buyer should act now instead of later.

A large bank loves the demo but says they won't buy from a seed-stage startup. How do you respond?

What they are checking: Whether they can handle vendor-risk objections honestly and find a path like a scoped pilot.

About the work

What do you know about identity governance, access reviews and provisioning, and how do buyers think about them today?

What they are checking: Whether they understand the IAM market well enough to hold a credible conversation with security leaders.

How do you run discovery with a security team to find out who has access to what and where their real pain is?

What they are checking: Whether their discovery is structured enough to uncover urgent problems that justify a new purchase.

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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. What will you do: • Own the full sales cycle end-to-end — from cold prospecting and structured discovery through high-stakes demos, commercial negotiations, and close — with no handoffs as an excuse to disengage. • Identify, prioritize, and penetrate Mid-Market and Enterprise accounts, navigating complex organizational structures to reach and influence the security, IAM, and IT stakeholders who control identity programs. • Apply MEDDIC rigorously across every active opportunity to drive forecast accuracy, expose risk early, and maintain consistently high win rates in competitive deals. • Maintain precise, up-to-date pipeline data in HubSpot — your hygiene standards will be the foundation as Oak scales from founder-led sales into a repeatable, process-driven revenue motion. • Partner directly with Oak's Tel Aviv product team to surface pattern-matched feedback from the field — translating what CISOs, IAM leads, and architects are telling you about identity attack surface, NHI risks, and access governance gaps into input that shapes the roadmap. • Act as a credible domain presence in conversations about IGA, identity lifecycle, and AI agent proliferation — buyers need to trust that you understand their environment before they'll open the door to Oak's IVIP. What you will bring: • 5–10 years of closing experience as an Enterprise Account Executive in high-growth SaaS, with a background in cybersecurity — you understand the pace, the pressure, and what it takes to operate in a hyper-growth environment. • Demonstrated track record of exceeding $1M+ annual quotas; you don't just hit your number, you own it. • Experience at an early-stage startup (Seed or Series A) — you know how to build pipeline and win deals without a mature playbook behind you. • Fluent in structured discovery and disciplined sales cycle management; you run a tight process and can articulate why at every stage. • Credible and compelling in the room with CISOs, VP-level security leaders, and executive sponsors — you speak their language and earn their trust quickly. • East Coast-based and ready to travel to customers; you close enterprise deals in person and know that presence matters at the finish line. • High-energy, self-directed, and coachable — you bring urgency and accountability to your pipeline, and you operate with the transparency and collaboration that makes the whole team stronger.

Apply at Oak Street Health