Staff Software Engineer jobs in Chicago, IL

You're embedded with a marketing team. How would you find the first agent worth building?

What they are checking: Whether they learn the domain and pick a high-value, buildable problem before writing code.

Walk me through how you'd harden a working AI agent pilot into something that runs reliably in production.

What they are checking: Experience with evaluation, monitoring, guardrails and failure handling at scale.

The CRM doesn't expose the data your agent needs. What do you do?

What they are checking: Resourcefulness in building integrations instead of stopping when a system falls short.

How do you evaluate an agent that writes campaign content, where there's no single correct answer?

What they are checking: Practical evaluation design with rubrics, SME review and regression sets.

Tell me about a time you turned a domain expert's knowledge into working software.

What they are checking: Skill at sitting in someone's workflow and translating expertise into tools.

What guardrails would you put on an agent that can post to social media or send emails?

What they are checking: Risk awareness about brand, approvals and irreversible actions.

As a staff engineer, how do you set technical direction for others without slowing them down?

What they are checking: Whether they lead other engineers through standards, reviews and mentoring instead of becoming a bottleneck.

A pilot works well in demos but marketers stop using it after two weeks. How do you find out why?

What they are checking: Focus on adoption and real workflows, since the goal is agents that stay live.