Top Tech Jobs & Startup Jobs in Chicago, IL

Manage enterprise employer relationships, drive product adoption, and help customers achieve hiring goals. Build trust with senior stakeholders, understand business objectives, configure workflows, provide consultation and training, and translate customer needs into product solutions. Use data to improve recruiting ROI and collaborate cross-functionally with Sales, Product, Marketing, Support, RevOps, and other teams. The role is remote-friendly with travel required as needed.

Manage a portfolio of enterprise employer accounts, driving renewals, upsells, cross-sells, retention, and expansion. Build executive relationships, conduct value-focused business reviews, demonstrate product impact using data, and partner with Customer Success to improve adoption. The role also supports customer events, escalations, account planning, forecasting, and scalable account-management processes in a high-growth SaaS environment.

Evaluate AI models for cybersecurity risks by crafting adversarial prompts and multi-turn attack chains. Assess model-generated malware, exploit code, phishing content, privilege-escalation scripts, and other offensive tooling for functional correctness and real-world exploitability. Score responses using harm taxonomies, document technical findings, develop evaluation frameworks, and collaborate with AI researchers, red teamers, and policy teams to improve model safety.

Stress-test large language models by crafting adversarial prompts and multi-turn scenarios that expose safety, bias, hallucination, prompt injection, and guardrail vulnerabilities. Evaluate model responses using harm taxonomies and severity rubrics, document findings, refine testing methods, and collaborate with engineers, data scientists, and researchers to improve AI safety and robustness. The role involves regular exposure to disturbing harmful content.

Own the full sales cycle for landing new Fortune 500 and Fortune 100 employer accounts. Build pipeline through outbound outreach, manage named accounts, lead executive conversations, run demos, negotiate complex six-figure partnerships, and close new business. The role requires disciplined forecasting, account planning, relationship building, customer events, and regular travel with high autonomy.

Evaluate AI models for dangerous CBRNE-related outputs, designing adversarial prompts, multi-turn attack chains, and threat models. Assess technical accuracy and real-world risk, distinguish open-source information from harmful uplift, score responses using severity rubrics, and document failures. Collaborate with AI researchers and policy teams to improve model safeguards and evaluation frameworks while following strict ethical and operational security protocols.