Top Tech Jobs & Startup Jobs in Chicago, IL

Lead WellTheory’s engineering organization as a player-coach, overseeing hiring, team development, technical direction, architecture, DevOps, reliability, compliance, AI-enabled development, and engineering processes. Partner with product and design on roadmap decisions while remaining hands-on in TypeScript and JavaScript codebases. Own engineering practices supporting HIPAA, SOC 2, and HITRUST requirements in a fully remote digital health company.

Owns multi-state payroll, HR compliance, benefits, leaves, accommodations, employee relations, policies, onboarding, and offboarding. The role serves as the primary People Operations contact while partnering with Finance, Recruiting, IT, Operations, and managers. It also focuses on building scalable systems, self-service resources, and AI-driven automation for a growing remote company.

Owns incident triage and resolution across the member app, clinical Care Hub, internal tools, and data pipelines. Responsibilities include reproducing issues, investigating logs and code, shipping durable fixes, prioritizing technical backlogs, writing runbooks, creating alerts and automations, and communicating with members and care teams. The role requires careful handling of protected health information and close collaboration within a remote engineering team.

Lead workforce capacity modeling, forecasting, and staffing strategy for Care Team operations. Build tools, dashboards, and processes to align resourcing with growth, support hiring and onboarding timelines, and analyze utilization to drive operational improvements across Care, Product, Marketing, and Finance.

Lead enterprise sales to employers and health plans: develop and execute sales strategies, source and manage pipeline, close deals through contracting and implementation, stand up and optimize sales programs, and collaborate cross-functionally to meet revenue targets.

Build and architect insurance and data infrastructure for eligibility, verification, and claims. Lead partner implementations to get employers, health plans, and channels live. Make technical decisions at the 0-to-1 stage, write clear documentation, maintain production systems, and use AI tools to scale impact on a fully remote team.

Lead sales operations and systems for a growing commercial team: own Salesforce, manage the commercial tech stack, design quotas and comp plans, coordinate events, build enablement materials, improve sales workflows, support analytics and business cases, and track core operating metrics to drive rep efficiency and process adherence.

Own and activate channel partnerships with health plans, PBMs, and care navigation orgs end-to-end: negotiate deals, build co-selling infrastructure, run joint pipeline reviews, operationalize launches, manage partner relationships, and ensure channel-sourced opportunities are tracked and closed (Salesforce). This is an individual contributor role requiring high ownership, travel (~10-20%), and startup-style execution.

Own and grow WellTheory's relationships with national and regional benefits consulting firms. Develop engagement strategy, present outcomes, create consultant-facing materials with Marketing, support employer sales, represent the company at events, keep consultants and sales aligned, collect market feedback, and travel extensively to build partnerships.

Lead and scale WellTheory's commercial go-to-market: build a high-performing sales organization, set GTM and revenue strategy, hire and coach a 20+ person team, generate pipeline, refine the sales playbook, and close enterprise employer and payer contracts.