Top Tech Jobs & Startup Jobs in Chicago, IL

Own strategic enterprise B2B SaaS accounts, driving adoption, retention, renewals, expansion, and net revenue retention. Build executive relationships, develop success and account plans, identify upsell opportunities, manage customer health and risks, coordinate cross-functional support, lead account reviews, and deliver training and best practices. The role also mentors team members and requires strategic communication with complex stakeholders.

Processes escrow disbursements for mortgage and consumer loans, including taxes, hazard insurance, and PMI. Reviews tax and escrow reports, reconciles general ledger accounts, performs loan setup quality checks, manages insurance and service-provider relationships, maintains servicing records, analyzes operational reports, and responds to client inquiries. The role also supports issue resolution, reporting, and departmental projects while maintaining accuracy and service quality.

Hands-on technical leader who designs, builds, and deploys production-grade AI automation and agentic workflows. Responsibilities include rapid prototyping, RAG and document-intelligence systems, API integrations, orchestration, monitoring, reusable AI assets, and mentoring a small engineering team to deliver frequent releases and measurable business impact.

Provide personalized customer support by phone, text, email, and social media. Guide business owners through payroll account setup, resolve escalated issues, and build strong customer relationships. Use AI to create support macros, Help Center content, and workflows, while improving processes and supporting customer acquisition, satisfaction, and retention goals.

Build and lead the sales enablement function by designing onboarding, training, certification, and product education programs. Partner with Sales, Marketing, Customer Success, Professional Services, Product, and commercial leadership to address performance gaps, improve ramp time, increase quota attainment, and support retention. Own enablement technology, including LMS and HubSpot-related training, measure program outcomes, evolve the sales motion, and guide the growing enablement team.

Build and lead development of full-stack agentic AI products for systems modernization. Responsibilities include creating coding harnesses and runtime layers, integrating source control, CI/CD, security, and developer tools, scaling coding-agent workflows, and partnering with customers, designers, and mission teams. The role requires production-grade, cybersecurity-compliant systems, strong product judgment, and close collaboration with forward-deployed engineering teams supporting national security missions.

Gather and document business requirements, collaborate with insurance carrier stakeholders, define scope decisions, and translate requirements into technical specifications for engineering implementation. Organize complex product configuration datasets and support data-driven solutions during a six-month implementation engagement.

Lead AMP's multidisciplinary engineering organization to define and execute technology vision and roadmap. Responsible for scaling teams across hardware, software, AI, and infrastructure; driving product development, quality systems, and reliable deployments; partnering with execs and cross-functional teams on budgets, prioritization, and metrics; recruiting and mentoring leaders; and balancing short-term delivery with long-term investments to create business value.

Own application security for backend services, APIs, cloud infrastructure, and edge systems handling financial transactions. Responsibilities include validating red-team findings, assigning severity, hardening services, implementing WAF and rate-limiting defenses, creating automated security configuration checks, expanding pull-request security gates, reviewing architectures, managing attack-surface coverage, and evaluating security tools. The role also partners with engineers and Security Operations to drive effective remediation.

Lead a team of software engineers building and scaling Spark’s broker productivity platform. Responsibilities include architecting full-stack solutions, guiding technical direction, reviewing code, managing infrastructure priorities, coordinating product planning, sequencing projects, coaching engineers, hiring, and ensuring reliable, high-quality delivery. The role balances hands-on engineering with people management and is fully remote within the United States.