Top Tech Jobs & Startup Jobs in Chicago, IL

Sell connectivity, data solutions, and AI-powered risk digitization software to insurance carriers and MGA clients across Canada. Responsibilities include developing strategic account plans, acquiring new logos, expanding existing accounts, managing executive relationships, negotiating renewals, forecasting sales, gathering market feedback, and meeting or exceeding quotas. The role uses a consultative solution-selling methodology and involves virtual, telephone, onsite, and industry-event engagements.

Lead portfolio strategy and operating layer for Product and Engineering: build prioritization frameworks, connect roadmaps to financial goals, define reporting/metrics for E-Team and Board, and drive cross-functional initiatives and decision-making.

Lead and grow a global data engineering team while establishing foundational data platforms and engineering standards. Design and oversee GCP-based pipelines, medallion data models, DataOps, monitoring, SLAs, CI/CD, governance, and data quality practices. Drive AI adoption across engineering workflows and build reliable, AI-ready data. Partner with business and technology stakeholders to prioritize roadmaps, deliver scalable solutions, and support data democratization.

Lead the architecture, development, and scaling of data pipelines and infrastructure for a customer-facing Data Lake platform. Build ETL and ingestion systems using GCP, Debezium, Pub/Sub, Dataflow, BigQuery, Python, Golang, and SQL. Establish engineering standards, deliver strategic projects, mentor engineers, influence cross-functional technical decisions, optimize data services, and shape the platform roadmap.

Lead UX design strategy for complex, high-volume B2B insurance workflows. Responsibilities include user research, information architecture, interaction and visual design, design systems, facilitation, storytelling, implementation planning, stakeholder alignment, and mentoring. The role shapes product vision across multiple teams and ensures scalable, accessible, consistent user experiences with measurable business and user impact.

Lead product vision, strategy, adoption, roadmap prioritization, user research, metrics, and cross-functional execution for an AI-powered B2B insurance submissions platform. Partner across design, engineering, marketing, customer experience, and operations; manage integrations with adjacent products; resolve dependencies; communicate strategy and outcomes to senior leadership; and mentor other product managers.

Lead North America agency adoption and engagement for Applied's commercial collaboration portfolio. Set strategy, build scalable operating models and playbooks, align cross-functional teams, and personally lead executive agency engagements and large migrations to drive day-to-day usage and bound premium. Combine human-led and digital adoption motions and reinforce network effects between agencies and carriers.

Lead product analytics for a B2B SaaS product: define metrics and measurement frameworks, analyze user behavior and product performance, build self-service dashboards, partner cross-functionally to link usage to business outcomes, and translate data into strategic recommendations for product roadmap and GTM decisions.

Secure LLMs, generative AI systems, ML infrastructure, training pipelines, and AI applications. Responsibilities include threat modeling, architecture reviews, security controls, hardening, vulnerability remediation, data privacy, incident response runbooks, vendor reviews, governance, policy development, and AI security training. The role also supports proof-of-concept security solutions and monitors emerging AI threats.

Design, deploy, and operate enterprise network infrastructure across data centers and cloud (GCP, AWS, Azure). Manage VPCs, VPNs, BGP, F5 BIG-IP, hybrid connectivity, and observability. Build IaC and automation with Terraform, GitLab CI/CD, and Ansible. Maintain monitoring, documentation, and participate in on-call support for critical incidents.