Top Tech Jobs & Startup Jobs in Chicago, IL

Owns administration, compliance, reconciliation, analytics, vendor management, and open enrollment for employee benefits programs. Leads the transition from fully insured or level-funded medical plans to self-funded plans, including plan design, stop-loss procurement, financial modeling, and implementation. Manages ACA reporting, ERISA, COBRA, HIPAA, PCORI, multi-entity compliance, carrier relationships, employee communications, audits, and benefits system integrations.

Processes and applies incoming payments, reconciles accounts receivable balances, investigates discrepancies, communicates with customers and internal teams, maintains documentation and reports, and supports month-end closing. The role requires basic accounting knowledge, Excel proficiency, strong attention to detail, and clear communication. Insurance billing experience and familiarity with ERP systems such as SAP or Oracle are preferred.

The Chief of Staff serves as a strategic partner to the CEO and COO, managing executive operating cadence, board and investor relations, enterprise initiatives, OKRs, strategic planning, and organizational effectiveness. The role leads fundraising strategy across venture, philanthropic, and government sources, including pipeline management, grant execution, investor materials, and stakeholder engagement. It also coordinates executive meetings, tracks KPIs, supports decision-making, and manages cross-functional projects. Travel to markets, conferences, and company meetings is approximately 20–25%.

Owns the intelligence platform roadmap for enterprise healthcare engagement, including decisioning, orchestration, integrations, interoperability, identity and consent management, and scalable deployment. The role defines strategy and requirements, prioritizes platform investments, leads partner integrations, establishes success metrics, and coordinates Engineering, AI/ML, Data Science, Security, Design, and client teams. It also embeds healthcare compliance, security, and responsible AI throughout the product lifecycle.

Leads a multi-phase enterprise systems integration following an acquisition, including NetSuite consolidation, master data migration, EDI transition, WMS and Shopify integrations, 3PL inventory relocation, and potential demand-planning implementation. Owns project plans, timelines, RAID logs, Agile ceremonies, budgets, vendors, risk management, stakeholder communication, data reconciliation, cutover planning, and post-migration handoffs across Finance, IT, Supply Chain, Operations, and external partners.

Edits branded content for articles, landing pages, newsletters, social copy, and other digital deliverables. Reviews grammar, style, tone, accuracy, facts, metadata, captions, links, and calls to action. Performs final quality assurance on preview links, maintains brand standards, collaborates with writers and production teams, and manages multiple assignments under deadline. The role is fully remote and requires extensive copy-editing experience, digital publishing or CMS familiarity, and exceptional attention to detail.

Leads customer data engineering strategy, delivery, team development, and roadmapping. Oversees data-driven product improvements, digital programs, quality initiatives, budgets, cybersecurity remediation, and portfolio management. Manages, mentors, and grows data engineering teams, including contractor teams, while guiding customer data platforms, omnichannel identity resolution, complex data modeling, and personalization-focused data science capabilities. Partners across the organization to execute strategic initiatives and build team capability.

Senior enterprise sales leader responsible for acquiring and expanding Fortune 500 brand and agency partnerships in creator and digital marketing. Owns the full sales cycle, from prospecting and presentations through negotiation and closing, while managing forecasts and revenue targets. Collaborates cross-functionally to develop customized influencer marketing solutions, demonstrates the platform’s value, represents the company as an industry thought leader, and mentors junior sales team members.

Manages Covius client relationships and leads account managers serving a mortgage-services portfolio. Develops business and technology solutions, advises clients, coordinates proposals and implementations, manages program performance, and collaborates with production, go-to-market, and senior leadership teams. The role requires expertise in loss mitigation mortgage processes, document generation and print fulfillment, relationship management with executives, and team supervision. This is a remote position with occasional travel or in-person meetings.

Leads the company’s marketing strategy, team, budget, brand, demand generation, content, thought leadership, events, digital presence, and AI-first marketing initiatives. Owns pipeline generation, marketing KPIs, attribution, dashboards, campaign optimization, and ROI reporting while partnering with sales and executive leadership. Oversees Salesforce and Pardot workflows, LinkedIn programs, employer branding, conferences, and integrated campaigns to drive measurable revenue growth.