Top Tech Jobs & Startup Jobs in Chicago, IL

Leads employee benefits and total rewards strategy, including self-funded health plans, compensation programs, vendor relationships, HRIS administration, compliance, claims analysis, cost containment, open enrollment, and executive reporting. Partners with leadership, Finance, and HR to optimize benefits, compensation, healthcare costs, and employee value.

Provide phone, email, and chat support to healthcare clinics using Verse Medical. Resolve ordering, product, shipping, and documentation issues; coordinate escalations with operations, billing, and customer success teams; guide product selection and order workflows; maintain accurate ticket records; update knowledge resources; and advocate for clinics and patients through empathetic, timely communication.

Manage small-business customer relationships, driving retention, satisfaction, renewals, and account expansion. Advise clients on maximizing ROI from HSI’s EHS and compliance solutions, engage senior stakeholders, identify growth opportunities, communicate customer insights to internal teams, and serve as a trusted technical advisor. The role includes revenue responsibility, quarterly targets, and maintaining a 95%+ net retention rate.

Researches and writes neutral, accessible content about U.S. public policy, court cases, legislation, executive orders, and reform proposals. Tracks policy developments and news across all 50 states, curates arguments and sources, edits and proofreads articles, and develops newsletters, webinars, presentations, and educational outreach materials. The role also uses spreadsheets and databases, collaborates with internal and external stakeholders, responds to feedback, and travels to related events as needed.

Develop and maintain proposal graphics, templates, layouts, icons, and visual systems for U.S. Government proposals. Translate complex technical concepts into compelling information design, provide rapid support during proposal deadlines, establish visual standards, update branding guidelines, and recommend improvements to corporate materials. Collaborate with proposal managers, writers, subject-matter experts, and leadership while explaining design decisions and ensuring visual consistency.

Manage approximately 15 digital banking clients across the Western U.S., driving retention, renewals, revenue growth, and product expansion. Build executive relationships, conduct business reviews, align digital strategies with client outcomes, present proposals, negotiate contracts, and promote multi-product adoption. Collaborate with sales, marketing, product, and implementation teams to support client success. Represent the company at trade shows, conferences, and client events.

Leads the company’s adoption of AI, analytics, automation, and business intelligence. Builds AI-powered workflows, Excel solutions, natural-language data interfaces, dashboards, forecasts, predictive analytics, and automated reporting using Snowflake, SQL, Tableau, and related tools. Partners across business functions to identify opportunities, improve data quality, automate repetitive processes, and deliver scalable decision-support solutions. Establishes responsible AI practices and advances an AI-first analytics culture.

Clean, standardize, enrich, and import product data into the PIM while maintaining data integrity and governance standards. Oversee bulk ingestion processes, leverage AI and automation, support data model improvements, resolve product listing issues, and contribute to data hygiene and workflow modernization. The role also involves collaborating with client-facing teams, documenting processes, proofreading product data, communicating progress, and adapting to changing priorities.

Lead North American enterprise sales for the Attribute FinOps product, managing 4–6 Enterprise Account Executives. Own regional revenue, pipeline generation, forecasting, GTM strategy, and new-logo acquisition. Recruit and coach a high-performing team, establish data-driven sales operations, improve CRM hygiene and sales performance, and support complex enterprise negotiations. The role requires credibility in Kubernetes, cloud-native infrastructure, and DevOps environments, plus strong SaaS sales leadership and business ownership.

Build and operate core HR processes, including onboarding, offboarding, performance reviews, merit and promotion cycles, career pathing, employee recognition, learning and development, benefits support, and immigration assistance. Own the implementation and configuration of Rippling, using AI tools to improve efficiency while maintaining compliant documentation, data handling, and decision-making practices. Partner closely with employees and managers in a growth-stage company.