Top Tech Jobs & Startup Jobs in Chicago, IL

Own Bestow’s total rewards portfolio, including compensation benchmarking, salary bands, merit and bonus cycles, equity administration, geographic pay ranges, benefits strategy, and renewals. Configure and maintain Pave, ensure HRIS data integrity, support job leveling, model equity programs, and partner with Finance, Legal, brokers, and the compensation committee. This hands-on role will build the company’s Total Rewards infrastructure from the ground up.

Leads the Insurance Product Configuration and Enrollment Platform Core, managing engineering managers and 20–30 engineers. Owns technical vision, distributed systems architecture, delivery commitments, operational excellence, testing strategy, partner implementations, and cross-team interfaces. Develops engineering leaders, manages hiring and vendors, and drives adoption of AI-augmented development tools and practices. Ensures scalable, secure, reliable platform services while balancing contractual delivery dates with long-term platform maintainability.

Own operational reporting, diagnostic analysis, capacity planning, platform administration, system changes, process improvement, and cross-functional program execution. Partner with Product, Engineering, workforce planning, vendors, training, and quality teams to improve operational performance. Lead accountability mechanisms, roadmap alignment, AI and automation initiatives, and scaled delivery while mentoring teammates and influencing without formal authority.

Lead a team of Technical Solutions Engineers to triage, diagnose, and resolve production issues across Bestow's platform. Own support queue, incident command, SLAs, runbooks, automation, observability, and partner escalation while contributing ~20% production-level code and converting recurring issues into funded roadmap work.

Own and improve the Product Development Lifecycle and product roadmap by architecting Jira/Confluence and AI-integrated tooling, building governance, dashboards, and metrics, enabling PM workflows, onboarding, release operations, and cross-functional stakeholder communications to increase velocity and product quality.

As a Staff Backend Engineer, you'll design and operate backend services, lead technical initiatives, ensure reliability, and mentor team members in a remote-first setup.

Lead execution of integrated demand generation campaigns across paid digital, email/nurture, SEO, ABM, and events. Manage paid budgets, Salesforce campaign structure, attribution and pipeline reporting, partner/vendor relationships, and martech stack. Align marketing to Sales through pipeline reviews, win-loss analysis, and account tiering. Use AI tools to scale personalization and optimize channel performance.

Own full sales cycle for net-new and expansion opportunities with life insurance carriers. Prospect, qualify, run discovery, present tailored demos, coordinate Sales Engineering, maintain pipeline and forecasting in Salesforce, and meet quota while selling value and ROI to senior stakeholders.

Lead frontend-leaning full-stack implementation work for carrier and enterprise integrations: architect reusable UI and API layers, author RFCs, guide technical delivery, enforce testing and security best practices, and partner with cross-functional teams to scope and ship production integrations.

Lead the New Business Experience product area across presales, application, and checkout. Own strategy, roadmap, and execution; manage and mentor product managers; run discovery and backlog hygiene; partner with engineering, design, marketing, and carriers; leverage AI-native workflows; define success metrics; and drive third-party distribution and partner-facing product strategy to convert prospects into policyholders.