Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full B2B SaaS sales cycle, from prospecting through negotiation and close, while meeting quotas and acquiring automotive dealership customers. Present AI solutions and ROI cases to executives, build pipeline through cold outreach, expand accounts through cross-selling and upselling, and collaborate with Client Success and Solutions Engineering. The role requires technical aptitude, complex deal experience, strong negotiation skills, and comfort working in an ambiguous early-stage startup.

Leads company-wide pricing and packaging strategy across products and verticals. Sets monetization vision, discounting guardrails, rate cards, bundling approaches, and pricing approval processes. Partners with executive, product, sales, marketing, customer success, and finance leaders to drive alignment, improve deal velocity, increase profitability, and support retention. Builds financial models, reporting, enablement programs, and implementation plans while adapting strategies to company goals.

Leads strategic, cross-functional programs for the Pricing & Inventory team, from opportunity discovery and beta testing through companywide scale. Translates business goals into roadmaps, coordinates data science, engineering, product, and business teams, manages timelines and trade-offs, and presents recommendations to executive leadership. Uses structured analysis, experimentation, and measurable outcomes to drive decisions in ambiguous environments.

Administers and improves employee benefits and leave programs, including health, retirement, disability, FMLA, accommodations, and annual enrollment. Ensures regulatory compliance, data accuracy, payroll reconciliation, vendor performance, employee communications, and timely case resolution. Partners with HR, Payroll, Legal, managers, employees, third-party administrators, and HRIS teams on complex cases, system testing, reporting, wellness programming, and process improvements.

Manage federal service contracts valued at approximately $5M–$10M, overseeing daily operations, staffing, finances, deliverables, quality assurance, reporting, risk mitigation, and customer satisfaction. Supervise employees, monitor budgets and profitability, support billing and invoicing, and assist with proposals, follow-on opportunities, and business development. The role works with the Prime Program Manager and requires occasional travel.

Leads the design and delivery of scalable data pipelines, dbt models, orchestration workflows, and analytical data models. Establishes data architecture, engineering standards, quality frameworks, governance, observability, and self-service analytics practices. Partners with stakeholders, leads technical reviews, mentors engineers, supports hiring, oversees analyses, and participates in incident response and continuous improvement.

Leads enterprise-wide AI strategy, governance, portfolio execution, ROI tracking, and responsible AI across multiple healthcare business units. Chairs AI governance bodies, manages initiative gating and investment decisions, coordinates clinical, operational, financial, vendor, compliance, and technology stakeholders, and drives measurable transformation outcomes. The role also leads AI talent development, organizational adoption, vendor discipline, clinical safety, regulatory readiness, and continuous improvement of the governance operating model.

Leads cybersecurity solutions engineering for government and education customers across managed security, network monitoring, cloud security, and related services. Provides technical discovery, solution design, demonstrations, proofs of concept, onboarding, deployment guidance, escalations, and post-sales support. Partners with sales and technical account teams, mentors engineers, develops enablement materials, informs product strategy, identifies expansion opportunities, and manages customer activity in Salesforce.

Manages a financial planning and analytics team supporting hospital executives and departments with business plans, forecasts, budgets, proformas, variance analyses, statistical reporting, and decision support. Oversees data validation, metrics, budget cycles, system integration, onboarding, reporting platforms, and continuous improvement initiatives. Partners with executive leadership, accounting, IT, Epic, Strategic Analytics, and Strata teams while guiding complex analyses and special projects.

Leads enterprise software sales across a SLED territory, acquiring new logos and managing the full sales cycle from prospecting through contract close. Builds relationships with C-level business and IT executives, qualifies technical and business requirements, presents ROI and TCO value, negotiates contracts, and achieves territory quotas. Develops regional sales strategies and partners with system integrators, channel partners, and alliances to expand new and existing revenue.