Top Tech Jobs & Startup Jobs in Chicago, IL

Analyze clinical outcomes, engagement, feature usage, ROI, and business trends for client reporting. Build and maintain complex SQL queries, reporting workflows, interactive dashboards, and self-service analytics. Partner with Customer Success, Sales, Marketing, Finance, Product, and Medical Affairs to deliver actionable insights, executive presentations, and client-facing materials. Improve data quality, automate recurring reporting, and identify opportunities that support client outcomes and business growth.

Lead large employer sales across the Eastern U.S. Mid-Atlantic, developing strategic relationships with benefits executives, consultants, brokers, channel partners, and prospective clients. Drive new business, manage complex sales cycles, deliver persuasive presentations, exceed quotas, communicate product value, and provide market insights. The role requires consultative selling, strong relationship-building, extensive travel, and daily use of AI tools to improve sales productivity.

The Director, Key Account Sales will develop and close new business with mid-market employers across Texas, Oklahoma, and New Mexico. Responsibilities include managing strategic relationships with benefits executives, consultants, partners, and health plans; meeting a $2M+ annual quota; delivering presentations; facilitating sales-to-customer-success transitions; and identifying upsell opportunities. The role requires consultative selling, direct and channel sales experience, strong relationship-building, heavy travel, and AI fluency.

Leads actuarial strategy, health economic research, cost-savings analyses, risk-based pricing, performance guarantees, and financial value demonstrations. Partners with sales, customers, consultants, health plans, and internal teams to communicate healthcare economics and support commercial growth. Analyzes medical and pharmacy claims, evaluates clinical and financial outcomes, presents executive-ready findings, and informs product strategy, market opportunities, and value-based contracting.

Leads actuarial strategy, healthcare economics, cost-savings analyses, risk-based pricing, performance guarantees, and financial value demonstrations. Partners with sales, customers, consultants, payers, and internal teams to communicate clinical and economic impact. Analyzes medical and pharmacy claims, oversees reserves, supports value-based contracting, evaluates new products, tracks healthcare market trends, and presents findings to executive and external audiences.

Lead product growth strategy across Hello Heart’s portfolio, owning activation, engagement, retention, experimentation, and shared growth metrics. Build and lead a hands-on growth team, identify member drop-off points, ship product experiments, establish operating mechanisms, and influence product leaders and executives through analysis, forecasts, and recommendations. Partner with marketing and data teams to improve the member journey while maintaining privacy, safety, and clinical guardrails in a regulated healthcare environment.

Lead Hello Heart’s FP&A function, overseeing financial planning, forecasting, three-statement modeling, revenue forecasting, management reporting, board materials, and resource allocation analysis. Partner with executives and cross-functional teams to improve financial insight and decision-making. Own planning software selection, automation, and AI-enabled reporting initiatives while transitioning away from manual spreadsheet processes. Manage and mentor a growing FP&A team and support investor and lender reporting.

Provide empathetic email and phone support to healthcare platform members. Investigate app, device, and account issues; resolve tickets; manage escalations; document cases; protect HIPAA-regulated information; and communicate proactively with members and internal teams. Monitor support metrics, identify recurring issues, suggest process improvements, and use approved AI tools responsibly to improve support workflows.

Leads client retention and expansion strategy for a healthcare technology portfolio. Builds executive relationships, drives renewals, contract negotiations, upsells, and revenue growth, while conducting market analysis and communicating client feedback internally. Partners with customer success, marketing, growth, product, clinical, and operations teams to improve client outcomes and product-market fit. Requires an MBA, consulting and healthcare experience, strong negotiation and relationship skills, and approximately 30–50% travel.

Provides legal counsel to product and commercial teams at a digital health company. Drafts and negotiates health plan, employer, partnership, data, technology licensing, MSA, BAA, and NDA agreements. Advises on AI-enabled products, privacy, intellectual property, product claims, healthcare regulations, CPOM, fee-splitting, telehealth, and fraud-and-abuse risks. Builds legal processes, templates, playbooks, and workflows while managing matters and providing practical risk guidance.