Top Tech Jobs & Startup Jobs in Chicago, IL

Own technical relationships with insurance carrier accounts by leading discovery, solution design, integrations, deployment support, defect management, QA, documentation, API and payload validation, SQL-based account monitoring, and incident management. The role partners with client engagement and engineering teams to ensure deployments meet carrier requirements and progressively assumes greater ownership of technical account relationships.

Source exceptional product management and design candidates for senior-level roles. Develop creative talent searches using LinkedIn Recruiter, Boolean techniques, portfolios, communities, conferences, referrals, and market research. Partner with recruiters and hiring managers to define candidate profiles, personalize outreach, build diverse pipelines, track engagement and conversion metrics, and maintain accurate records in Ashby or a similar ATS. Use AI tools to improve research and sourcing efficiency.

Own technical delivery and account health for insurer software deployments. Responsibilities include discovery, solution design, integrations, API and payload review, QA testing, defect documentation, workflow mapping, SQL-based production monitoring, incident management, and technical communication with carrier accounts and engineering teams.

Own complex, client-facing programs from scoping through launch and long-term success. Translate enterprise client priorities into execution plans, coordinate Product, Engineering, Client Engagement, and customer stakeholders, manage risks and dependencies, and maintain launch readiness. Build scalable operating rhythms, status tracking, escalation processes, and decision logs while identifying patterns that improve client delivery and product operations.

Owns core accounting operations, including ERP administration, Ramp transactions, accounts payable, balance sheet schedules, payroll entries, bank reconciliations, accounts receivable, flux analysis, and sales and use tax filings. The role ensures accurate financial reporting, GAAP compliance, clean accounting data, timely reconciliations, and effective coordination with vendors and internal stakeholders.

Lead the evolution of Assured’s design system, defining shared patterns, standards, tools, and infrastructure across Design, Product, Brand, and Engineering. Improve craft, consistency, accessibility, and scalability while exploring AI-enabled design workflows. The role combines strategic leadership with hands-on product, interaction, and visual design work to enable teams to build high-quality experiences efficiently.

Source and engage exceptional software engineering talent for Staff+ roles during a 90-day contract. Develop creative searches using LinkedIn Recruiter, GitHub, technical communities, blogs, and unconventional channels; personalize technically credible outreach; partner with recruiters and hiring managers; track pipeline and conversion metrics; maintain candidate data in Ashby; and use AI tools to improve research and sourcing efficiency.

Own cross-functional carrier projects from requirements scoping through launch, translating between client-facing teams and Engineering. Build product operations processes, prioritization frameworks, reporting cadences, RAID logs, dependency maps, and launch plans. Identify recurring carrier needs for platform improvements, manage ambiguity and tradeoffs, and use AI tools such as Claude to accelerate requirements, documentation, and dependency tracking. The role can grow into long-term platform product ownership.

Leads Assured’s integrated marketing and named-account growth engine across top U.S. property and casualty insurance carriers. Owns ABM/PBM, paid, digital, SEO/AEO, events, lifecycle, web, attribution, and the marketing-to-sales SLA. Builds and manages a senior AI-first team, partners with sales and founders, instruments account-level performance, drives category visibility, and ensures compliance with carrier anti-bribery requirements.

Lead high-priority, cross-functional strategic and operational initiatives end-to-end. Structure complex problems, analyze data and qualitative insight, prepare executive-ready materials, coordinate programs across Product, Engineering, Sales, Finance and Legal, track strategic agenda and unblock decisions, and provide surge support for GTM by building customer-facing materials and driving implementation.