Top Tech Jobs & Startup Jobs in Chicago, IL

Recruiter responsible for high-volume sourcing, vetting, candidate engagement, and contracting of 1099 healthcare providers across multiple states. The role manages recruiting pipelines, outreach, scheduling, funnel metrics, candidate communication, and workflow improvements. Success requires accelerating time-to-contract, maintaining strong pipeline organization, using sourcing and ATS tools, and building scalable recruitment processes in a fast-paced virtual healthcare startup.

Own payer and employer partner implementations from launch planning through value reporting and renewal. Translate contracts into eligibility, benefits, outreach, workflow, and data requirements; coordinate engineering, clinical, data, growth, and customer success teams; define success metrics and dashboards; present results to partners; and convert lessons into scalable processes, checks, templates, and product requirements.

Own revenue reporting, dashboards, CRM data quality, funnel analysis, revenue technology, and AI-powered workflow improvements. Analyze data using Salesforce or SQL, manage tools such as Outreach, Clay, and Gong, improve go-to-market processes, and deliver actionable insights to Sales, Marketing, Customer Success, and Finance leaders.

Lead Pomelo Care’s enterprise security governance, risk, and compliance program. Own SOC 2 Type II and HITRUST certification lifecycles, security policies, access governance, HIPAA risk assessments, awareness training, control monitoring, incident response, and third-party risk assessments. Partner with engineering leadership to align technical roadmaps with security strategy, represent the company during audits and partner due diligence, and report security posture and program maturity to executives.

Own end-to-end delivery of complex software features for a virtual care platform. Design scalable systems, build AI-powered agents and workflows, enhance reliable mobile and web experiences, and translate clinical and user needs into technical solutions. Collaborate with product managers, designers, and clinical staff while focusing on patient impact, product quality, and engineering efficiency.

Leads enterprise sales growth with large and jumbo employers. Owns market development, prospecting, buyer-specific strategies, proposals, negotiations, and the full end-to-end sales cycle. Builds relationships with C-suite executives, benefits leaders, health plans, and benefits consultants while achieving quota goals. Requires extensive experience selling to large employers, strong presentation and organizational skills, Salesforce proficiency, healthcare and digital health familiarity, and cross-functional collaboration. The role is fully remote within the continental United States with travel as needed.

Own the performance creative lifecycle for Pomelo’s menopause program, including patient research, trend analysis, concept development, asset production, creative operations, and campaign performance analysis. Build efficient workflows, manage agencies and creators, accelerate testing cycles, and use paid-channel data to scale winning concepts and retire underperforming assets. Partner with Growth and cross-functional teams to balance brand identity, clinical nuance, and direct-response performance.

Own and grow Pomelo Care’s commercial payer pipeline across the complete health-plan sales cycle. Responsibilities include developing go-to-market strategies, building executive and operational stakeholder relationships, negotiating contracts, analyzing pipeline data, creating proposals and presentations, and collaborating with Partnerships and Marketing. The role also advocates for customer needs internally and supports strategic growth initiatives in a remote, cross-functional environment.

Own and accelerate the health plan partnership pipeline through strategic research, opportunity sourcing, deal strategy, presentations, pricing models, and contracting support. The role identifies high-value payer opportunities, drives deal velocity, advocates for prospects internally, and leads cross-functional growth initiatives with Partnerships, Marketing, Legal, and Compliance. Candidates need healthcare and health plan experience, strong analytical, communication, project management, and commercial problem-solving skills. The role is fully remote within the continental United States.

Provide healthcare regulatory legal guidance for a virtual medical practice. Advise on telehealth, professional licensure, scope of practice, corporate practice of medicine, fraud and abuse laws, Medicaid reimbursement, ERISA, health plan design, marketing communications, and virtual care expansion. Partner with clinical, legal, compliance, and business teams on clinical model design, state launches, risk assessment, and regulatory matters.