Top Tech Jobs & Startup Jobs in Chicago, IL

Serve as the technical face and trusted advisor for customers, designing platform configurations, delivering training, leading technical discovery and escalations, and advocating customer needs to Product and Engineering to drive adoption and expansion.

The Senior Web Application Penetration Tester will conduct assessments, analyze security findings, collaborate with clients, and draft detailed reports on vulnerabilities and remediation steps.

Lead growth strategy and execution for a portfolio of high-growth DTC brands across paid media, creative, influencer marketing, offers, funnels, and CRO. Own performance, scale decisions, testing roadmaps, and cross-functional pod alignment while partnering with founders and senior stakeholders to drive measurable revenue, efficiency, and retention improvements.

Drive enterprise sales for Progyny's Family Building solution by developing territory strategy, building pipeline, and closing complex deals with large employers and benefits consultants. Serve as a trusted advisor, deliver presentations and demos, manage pipeline in Salesforce, collaborate cross-functionally, gather market feedback, and exceed annual sales targets while traveling to client meetings and industry events.

Design and build backend services, APIs, SDKs, and user-facing systems enabling secure agent-to-agent financial interactions. Implement cryptographic identity, payment workflows, transaction processing, reputation tools, and scalable infrastructure for AI-native financial products.

Provide remote executive support including calendar and travel management, call/email screening, briefing prep, vendor and project deadline tracking, document preparation, CRM data entry, and ad hoc administrative tasks.

Handle customer inquiries across phone, email, chat, and social media; use Zendesk to track interactions; troubleshoot and resolve issues; document cases; collaborate with teams to improve processes and meet performance metrics.

Develop and manage SEO-optimized content and social media calendars using AI tools and external creators. Oversee platform backend, coordinate with technical support, build influencer partnerships, analyze performance with analytics tools, and refine strategies to increase engagement and reach.

Serve as the UAE-resident nominee director (no day-to-day operations). Handle appointment paperwork, sign acceptance/resignation and bank account documents as needed, and ensure basic UAE legal and regulatory compliance in a nominee capacity.

Lead UI/UX design for an AI-driven pharmaceutical research platform: create wireframes, prototypes, visual designs, conduct user research and usability testing, collaborate with AI engineers, maintain product backlog and brand guidelines, and build web interfaces using HTML/WordPress.