Top Tech Jobs & Startup Jobs in Chicago, IL

Lead UX/UI design for complex B2B insurance software, delivering high-fidelity Figma designs, maintaining design systems, conducting user research, improving workflows with AI, partnering with engineering, and shaping product decisions. The role also documents processes, supports team development, and teaches design techniques. This is a temporary, full-time assignment expected to last approximately 12–16 weeks, with potential extension.

Own day-to-day commercial contracting, including drafting and negotiating SaaS, vendor, reseller, partner, privacy, and data-processing agreements. Advise Sales, Finance, Procurement, Product, Compliance, and Customer Success on routine legal terms, escalate nonstandard risks, and support contract intake, approvals, execution tracking, templates, playbooks, and lifecycle management. Assist with HIPAA, privacy, intellectual property, open-source licensing, and post-acquisition contract integration matters.

Build and lead Talkiatry’s commercial enablement function, initially supporting field-based provider partnerships. Design onboarding, training, certification, playbooks, and continuous development programs; assess capabilities and skill gaps; partner with commercial leaders on coaching and adoption; and measure program impact on productivity and performance. The role also reinforces company culture and scales enablement across the broader commercial organization.

Administer and enhance Apartment Life’s HubSpot environment, integrations, automations, workflows, permissions, data structures, dashboards, and reporting. Handle helpdesk requests, data cleanup, audits, system-generated work, onboarding and offboarding, and synchronization issues. Build and test Node.js workflow actions and API integrations, maintain system stability and data integrity, document solutions, and collaborate with technology leadership and cross-functional teams in a fully remote environment.

Own customer success for government accounts by driving adoption, retention, renewals, expansion, and customer outcomes. Develop account strategies, train users, monitor success metrics, manage stakeholders, de-escalate risks, and advocate for customers internally. The role requires cross-functional collaboration with Product, Sales, and Support, plus customer visits and conferences approximately 15–20% annually.

Develops hospital service lines through physician outreach and provider relationship management. Conducts in-person sales meetings, analyzes referral patterns, researches provider needs, presents hospital services, and communicates client feedback to hospital leaders. Creates and executes market business development strategies, maintains CRM records, prepares sales reports, resolves provider concerns, and supports network development initiatives. Requires regular travel within the market and adherence to healthcare referral and ethical compliance policies.

The Customer Success Architect guides customers through SaaS onboarding and implementation, coordinates milestones and project scope, connects product capabilities to customer workflows, resolves concerns, and advocates for customer success. The role builds relationships with users and executive sponsors, collaborates across Customer Success, Sales, Support, Product, and R&D, and shares customer insights to improve implementation practices. US-remote with 10% travel to customer sites and events.

Own product marketing for Escape’s application security platform, defining positioning, messaging, go-to-market strategies, launch plans, competitive research, thought leadership, and sales enablement. The role translates technical security capabilities into compelling narratives for security leaders and engineers, supports pipeline growth, and establishes scalable product marketing processes across US and European markets.

Staff qualified contractors onto client projects by sourcing, screening, matching, onboarding, and tracking them through their first billed hour. The role manages high-volume contingent staffing, collaborates with delivery and operations teams, maintains ATS and staffing data, redeploys contractors, and reports on fill rates, time-to-staff, time-to-billing, and utilization.

Own Lantern’s identity control plane, including lifecycle automation, access management, federation, privileged access, secrets, workload identities, and identity-as-code. Establish Zero Trust, RBAC/ABAC, phishing-resistant MFA, Conditional Access, and verification standards for regulated healthcare systems handling PHI. Partner with cloud, platform, service delivery, and governance teams while serving as the technical authority reporting to the CISO. This hands-on principal role requires automation, structural control improvements, and independently verifiable enforcement.