Top Tech Jobs & Startup Jobs in Chicago, IL

Owns strategic enterprise sales for consumer-directed healthcare benefits, managing named accounts and complex 9+ month sales cycles. Responsibilities include stakeholder mapping, discovery, business-case development, technical demos, procurement and legal coordination, forecasting, and closing high-value B2B partnerships. The role requires executive communication, multi-threaded relationship building, technical integration fluency, and experience with HSA, HRA, FSA, benefits platforms, or related markets.

Leads software quality assurance for workflow-based applications, creating test plans, automated test cases, and reusable automation frameworks. Executes functional, regression, smoke, and performance testing; validates workflows, integrations, business rules, security, and data flows; tracks defects; and supports Agile ceremonies. Collaborates with product owners, engineers, and platform teams to define acceptance criteria and improve testing processes. The role also mentors quality engineers and communicates product quality status.

Lead and manage a QA team to design and implement QA strategy, automation, and testing frameworks for SaaS and on-prem products. Drive test planning, automation (UI/API), CI integration, metrics reporting, root-cause analysis, and continuous improvement while mentoring engineers and collaborating with cross-functional teams to ensure timely, high-quality releases.

Design, develop, and deliver scalable .NET back-end and front-end solutions within an Agile, DevOps-oriented team. Lead technical design, code reviews, testing-first practices, CI/CD pipelines, containerized deployments, and ensure non-functional requirements (security, performance, scalability, maintainability). Mentor peers and collaborate across product, design, and architecture to produce high-quality software.

The Sales Executive is responsible for building business in middle markets, managing relationships, and overseeing all business development efforts in assigned territories.

Drive revenue by developing relationships with title companies, CRE firms, brokers, attorneys, and financial professionals. Execute territory-based business development plans, manage full sales cycle from prospecting to onboarding, represent Accruit at industry events, collaborate with internal teams, and maintain CRM pipeline and forecasts to grow 1031 exchange and CRE-related business.

Serve as a senior technical leader shaping architecture strategy, roadmaps, and standards across product teams and portfolios. Guide cross-system integration, cloud-native and distributed designs, governance, risk management, and operational resiliency. Mentor architects, lead architecture reviews, influence enterprise technology decisions, and align technology investments with business priorities.

Senior Cloud Security Engineer responsible for hands-on remediation of cloud and infrastructure vulnerabilities, operating vulnerability and CSPM tooling, enforcing secure configurations across Azure environments, embedding security in CI/CD and IaC, supporting compliance/audits and reporting, mentoring engineers, and partnering with cross-functional teams to maintain cloud security posture and policy.

Support product and operations teams to design, document, and deliver scalable workflow solutions. Elicit and translate business, compliance, and operational requirements into testable user stories, process maps, and rule catalogs. Drive cross-functional alignment, operational readiness, and post-launch measurement to reduce risk and improve performance.

Responsible for the full software development lifecycle, collaborating with teams to design, develop, and maintain applications while mentoring others and ensuring engineering standards.