Top Tech Jobs & Startup Jobs in Chicago, IL

Leads federal technology solution architecture, capture, and proposal development for healthcare and defense agencies. Designs enterprise architectures across cloud, modernization, data, interoperability, DevSecOps, cybersecurity, and AI. Translates solicitations into technical approaches, staffing models, implementation plans, and persuasive proposal content. Facilitates solution reviews, presentations, and partner discussions while applying VA healthcare and enterprise systems expertise. Supports responsible AI, technical governance, technology evaluations, and modernization roadmaps.

Develop and execute Palo Alto Networks technical go-to-market strategies, support strategic cybersecurity sales opportunities, create technical campaigns and proof-of-concepts, and build company-wide enablement and certification programs. Partner with sales, engineering, professional services, and vendor teams to generate pipeline, drive cross-sell and competitive displacement, support executive engagements, and improve technical readiness across eight regions.

Own full-cycle recruiting across the US for Dynamic Connections and its acquired portfolio companies. Build talent pipelines, develop hiring plans, source and close candidates, manage recruiting systems, navigate state-specific hiring requirements, benchmark compensation, and ensure a consistent candidate experience. The role focuses heavily on recruiting for logistics, transportation, sales, operations, and carrier representative positions while partnering with leaders and supporting efficient onboarding handoffs.

Manage Egnyte’s website content, structure, performance, and optimization. Lead web projects from scope through launch, collaborate with marketing, creative, development, analytics, and sales teams, and use analytics, SEO, AEO, and conversion testing to improve results. Maintain accurate site content, guide designers and agencies, review implementations for accessibility and speed, and prioritize initiatives based on business impact.

Lead paid user acquisition for TripleTen’s advanced programs across the US. Own approximately $200K monthly budgets, Meta and Google campaigns, funnel strategy, experimentation, attribution, conversion tracking, and traffic quality. Analyze CRM, BI, sales-call, and cohort data to optimize full-funnel economics. Expand into additional channels, launch program-specific funnels, brief creative teams, and apply AI tools to improve campaign analysis and decision-making.

Develop and deliver high-volume enterprise applications across the full software development lifecycle. Design, code, test, debug, optimize SQL solutions, troubleshoot complex issues, contribute to scalable architecture, collaborate with technical and business stakeholders, and mentor other developers. Work independently while participating in Agile development and production implementation.

Conduct web, mobile, API, network, and social engineering penetration tests; identify vulnerabilities, develop technical reports, recommend mitigations, and present findings to clients. Ensure assessments align with GDPR, PCI-DSS, SOC 2, and other standards while tracking emerging threats. The role is remote and contract-based, with cloud security, certifications, mobile testing, API security, and scripting experience preferred.

Generates qualified meetings and early-stage opportunities through phone, email, social, and multi-channel outbound prospecting. Researches accounts, engages healthcare decision-makers, conducts discovery, qualifies prospects, handles objections, and transitions opportunities to Regional Sales Directors. Maintains CRM data, supports account-based marketing, shares account intelligence, and partners with Sales and Marketing to improve targeting, messaging, and pipeline growth.

Found and operate a scalable enterprise account management motion across hundreds of accounts. Use agentic workflows to assess customer health, prioritize outreach, drive adoption, realize value, support retention and expansion, identify whitespace, and develop reusable playbooks. The role combines customer success, account relationship management, AI adoption, and operational design in a high-velocity environment.

Develops and executes marketing strategies for a portfolio of properties, analyzing leasing and campaign performance, reporting results to leadership and clients, and recommending KPI-driven improvements. Responsibilities include creating marketing action plans, campaigns, social media initiatives, training onsite teams, coordinating vendors, and presenting strategic recommendations. The role requires property visits, conferences, and training travel of approximately 25% annually.