Top Tech Jobs & Startup Jobs in Chicago, IL

Entry-level HR Generalist providing full-cycle HR support for locations in the US, Canada, and Puerto Rico. Duties include talent acquisition, employee relations and investigations, HRIS recordkeeping, performance management, benefits and payroll administration, wage and labor compliance, workers' compensation and safety, reporting, and HR projects. Acts as primary HR contact and advises managers on HR matters.

Manage filing and follow-up of FHA Part B and non‑conveyance claims (CWCOT, SFLS) and loss mitigation claims (PFS, Partial, SFB, Mod, HAMP). Monitor title package submissions, resolve suspended claim exceptions, track payments, maintain reports/queues, and meet investor/HUD timelines to minimize losses.

Lead and grow a Western U.S. enterprise sales organization for managed infrastructure, colocation, and cloud services. Combine hands-on selling in complex deals with coaching, pipeline management, forecasting, hiring, and cross-functional alignment to drive new business and account growth.

Manage client relationships to drive adoption, retention, and success with Teachstone solutions. Lead onboarding, implementation, renewals, health monitoring, reporting, and proactive communication. Serve as client advocate, deliver presentations, gather feedback, and collaborate cross-functionally to optimize product usage and outcomes.

Provide HR subject-matter expertise and operational support for employment events (hires, changes, departures). Ensure managers and employees receive appropriate HR resources and partner support; manage payroll and HRIS processes; maintain confidentiality; navigate complex employee issues; and communicate and consult effectively with internal and external stakeholders.

Lead end-to-end UX for native iOS and Android mobile products for healthcare providers. Conduct user research and validation, design clinical workflows, evolve mobile design system components, partner with Product, Engineering, Compliance, and mentor junior designers. Drive product strategy through evidence-based design and support implementation through prototyping and build reviews.

Verify and quality-check evaluation tasks for frontier AI models: confirm correct answers and evidence, spot and explain errors, apply skeptical verification, and communicate concise findings. Work remotely ~20 hours/week on a one-month contract (possible extension), meet delivery deadlines, and prioritize what needs deeper review versus quick resolution.

Lead post-onboarding customer journey across adoption, support, renewals and expansion. Manage and grow a remote account management and frontline support team, build AI-driven support stacks, drive retention and NPS metrics, partner with implementation and product, and own renewal/expansion playbooks.

Build and lead a remote outbound SDR/Outbound Sales Executive function from scratch: hire and train reps, design outbound processes and playbooks, select and integrate the outbound tech stack, run high-volume dial-led campaigns into physical security and corporate real estate buyers, and own SAL/SQL targets, reporting, and cross-functional alignment with Sales, Marketing, IT, and RevOps.

Lead complex technical investigations and resolve high-impact client issues for a clinical AI SaaS product. Own ticket lifecycle, coordinate cross-functional teams, improve support processes and documentation, mentor junior analysts, and communicate clearly with clinical and operational stakeholders.