Top Tech Jobs & Startup Jobs in Chicago, IL

Leads Sales and Revenue Operations across sales, customer success, partnerships, and channel teams. Develops GTM strategy, forecasting, pipeline management, sales compensation, process improvements, technology roadmaps, and commercial planning. Builds high-performing operations teams, drives cross-functional alignment, supports AI transformation, and improves revenue productivity through data, systems, and operational excellence.

Leads discovery and strategic partnerships with payers, PBMs, and providers to expand virtual-first healthcare solutions. Identifies product opportunities, shapes integrations and tools, supports high-impact initiatives, mentors product managers, and establishes objective-tracking practices. The role requires cross-functional alignment, customer research, data analysis, strong communication, and experience launching 0-to-1 products in ambiguous environments.

Leads ambiguous, high-impact product and design initiatives from problem framing through validated experiences and launch. Owns product direction, multi-quarter roadmaps, prioritization, vision, prototyping, research, data-informed decisions, executive communication, and cross-functional alignment. Partners with engineering, clinical, legal, regulatory, operations, and commercial teams while using AI-assisted tools to accelerate research, design, specification, and analysis.

Own Omada Health’s employer sales business, driving new and expansion bookings across employer segments. Develop go-to-market, segmentation, channel, pricing, and coverage strategies; lead strategic enterprise deals and executive relationships; coach sales leaders; build a scalable, high-performing sales organization; and influence product, clinical, marketing, payer, finance, and customer success decisions. The role requires extensive enterprise healthcare sales leadership, employer ecosystem expertise, and experience scaling teams and complex commercial partnerships.

Leads two infrastructure and engineering systems squads, owning roadmap, prioritization, delivery, operational health, hiring, mentoring, and vendor budgets. Ships production code, manages on-call performance, oversees audits and automation, and partners across engineering and business functions. Requires substantial software engineering and people-management experience, hands-on production development across cloud or application technologies, strong CI/CD and observability knowledge, security awareness, and experience directing AI agents in production workflows.

Build and maintain automation, integrations, file-processing tools, migrations, and other software that reduces operational toil. Investigate root causes, resolve implementation and escalation issues, develop reusable solutions, and support systems through on-call participation. Partner with commercial, product, and engineering teams while using Ruby on Rails, APIs, workflow automation platforms, and AI-assisted development. The role also involves debugging, optimization, code quality, and ramping onto unfamiliar systems.

Designs and delivers complex cross-system integrations, APIs, automation workflows, and reusable engineering solutions. Diagnoses root causes, improves reliability, documents risks and runbooks, participates in on-call support, and partners with commercial, product, and engineering stakeholders. The role also mentors engineers and non-engineers, guides technical trade-offs, scopes ambiguous problems, and delivers measurable operational improvements.

Own the end-to-end B2B2C enrollment funnel for Customer Success, including reporting, data modeling, funnel metrics, dashboards, attribution, and operating cadences. Identify data and process gaps, deliver decision-ready recommendations, lead stakeholder reviews, and drive cross-functional improvements across Operations, Customer Success, Marketing, and Engineering. Lead annual Customer Success planning for capacity, territories, quotas, incentives, roadmaps, and targeting.

As Chief Revenue Officer, lead Omada Health's commercial strategy to drive growth, market access, and integration of AI in operations, ensuring sustainable success across healthcare channels.

Lead backend-focused engineering to design and ship member- and care team-facing experiences. Own architecture end-to-end, set technical direction and quality standards, mentor engineers, and deliver scalable, secure APIs with CI/CD, cloud deployments, and GenAI/LLM-informed workflows.