Top Tech Jobs & Startup Jobs in Chicago, IL

The Payroll Customer Success Manager serves as the main contact for customers, supporting onboarding, ensuring payroll accuracy, resolving issues, and building trust through proactive communication.

Improve AWS production infrastructure reliability, observability, performance, and operational maturity. Build Terraform infrastructure, enhance CI/CD, automate operational work, manage incident response and on-call operations, lead postmortems, improve application resilience, support capacity planning and database reliability, and collaborate on security hardening and compliance. Mentor engineers and promote reliability practices across the organization.

Provides strategic in-house legal support focused on vendor, technology, professional services, and healthcare agreements. Drafts and negotiates contracts, manages the contract lifecycle, advises on healthcare regulatory and compliance matters, partners with executives on business risks, develops legal training, promotes CLM tools, and manages outside counsel. Requires a law degree, active state bar membership, and at least four years of legal experience.

Lead and grow Proof’s IT Engineering team while transforming corporate IT from reactive help desk support into an engineering-first function. Own the strategy and roadmap for identity, access, endpoints, SaaS, vendors, procurement, and budgeting. Mentor engineers, implement infrastructure-as-code, CI/CD, GitOps, automation, and AI-driven operations, reduce ticket volume through root-cause fixes, and partner with InfoSec on security and compliance.

Leads complex telecommunications and network modernization programs involving multiple projects. Coordinates project managers, technical teams, vendors, and business stakeholders; manages integrated plans, governance, risks, dependencies, resources, budgets, and forecasts. Ensures operational readiness, production transitions, stakeholder communication, strategic alignment, and benefits realization. Supports continuous improvement and maintains delivery discipline across technology initiatives.

Lead global accounting operations and financial reporting across 14 international entities. Manage a 15-person finance team, oversee US GAAP and statutory compliance, direct consolidations and close processes, improve accounting workflows using modern technology, and provide accurate reporting to executives, the board, banks, and investors. Establish scalable policies, automate processes, manage accounting functions, and support the company’s rapid growth.

Source, engage, assess, and manage executive-level candidates for clients. Coordinate interviews, manage candidate expectations, maintain pipelines and networks, collaborate with sourcing, and deliver high-quality placements in a remote environment.

Own long-term relationships with enterprise legal and marketing teams from go-live through renewal. Drive product adoption, expansion, account health, executive business reviews, measurable customer value, and renewal support. Configure the platform, analyze usage, manage customer cadence, translate feedback into product input, and build Blee’s customer success playbook. The role requires enterprise SaaS experience, technical fluency, executive communication, and 10–20% customer travel.

Leads two vertical software businesses with full ownership of revenue, retention, profitability, cash management, product direction, organizational structure, and customer relationships. Builds repeatable sales and renewal motions, manages public-sector procurement, allocates capital across functions, evaluates teams, and sets coordinated product strategies while preserving each business’s identity. The role requires hands-on selling, P&L leadership, founder-transition experience, and approximately one week of travel per month.

The People Analytics and HRIS Analyst develops workforce dashboards, reports, visualizations, and trend analyses using HR data. The role supports Workday reporting, configuration, data quality, governance, testing, and HRIS changes. It partners with HR leaders and business stakeholders to translate workforce questions into actionable insights related to retention, hiring, compensation, talent, engagement, and organizational effectiveness. The analyst also establishes reporting standards, ensures data security, and educates stakeholders on interpreting people analytics.