Top Tech Jobs & Startup Jobs in Chicago, IL

Leads and scales Omilia’s regional or global pre-sales function, managing Solution Consultants and Demo Engineers while driving technical quality and revenue outcomes. Oversees solution architecture, demonstrations, RFPs, technical handoffs, forecasting, enablement, recruiting, and team development. Personally supports strategic enterprise opportunities, executive presentations, and complex integrations involving conversational AI, CCaaS, SaaS platforms, and APIs. Partners with Sales, Product, and Delivery leadership to manage risk, improve methodology, and translate customer insights into roadmap priorities.

Own the SentinelAgent clinical trial AI platform from early pilots through validated, multi-sponsor deployment. Responsibilities include product requirements, backlog and roadmap management, engineering coordination, regulated integrations, GxP validation, AI governance, privacy and security controls, release gates, auditability, and performance instrumentation. The role requires extensive eClinical product management experience, clinical systems integration literacy, knowledge of global regulations, and experience shipping locked-model AI products in validated environments.

Lead sa.global’s North American country operations, translating global strategy into local execution. Own shared P&L performance, revenue growth, delivery quality, client outcomes, regulatory compliance, workforce planning, and cross-functional alignment. Champion AI-enabled offerings and ways of working, represent the company with clients and partners, and serve as the senior in-country leader connecting global functions with local commercial and operational realities.

Monitor systems and networks in a global 24/7 security operations environment, investigate and respond to cyber incidents, analyze post-event activity, assess vulnerabilities, and deploy countermeasures. The role requires familiarity with cloud security controls, threat intelligence, operating systems, network and web technologies, scripting, penetration testing tools, and vulnerability management. Strong analytical, communication, collaboration, and problem-solving skills are essential.

Leads FP&A, budgeting, forecasting, long-range planning, SaaS metrics, management and board reporting, cash flow analysis, and financial business partnering. The role improves finance systems, automation, data governance, and AI-enabled workflows while mentoring the finance team and supporting strategic decisions, operational excellence, and organizational growth.

Owns a named territory of community and regional health systems, developing executive relationships and leading consultative, multi-stakeholder enterprise sales. Responsibilities include conducting site visits, building system-specific business cases, presenting financial, operational, and clinical value to C-suite buyers, managing 6–12-month sales cycles in Salesforce, coordinating subject-matter experts, and contributing to the regional sales playbook. The role requires extensive territory travel and frequent engagement with healthcare executives.

Leads FP&A, budgeting, forecasting, long-range planning, SaaS metrics, management and board reporting, cash flow analysis, and financial systems improvement. Partners with executives and functional leaders on strategic decisions, investments, and accountability. The role also drives automation and AI-enabled finance workflows, improves data governance and operational efficiency, and mentors the finance team while scaling processes in a high-growth B2B SaaS company.

Own the B2B product experience from enterprise enrollment through renewal and expansion. Lead customer discovery, intake, roadmap prioritization, enterprise integrations, onboarding, engagement, analytics, and AI-powered learning insights. Partner closely with sales, customer success, engineering, legal, and enterprise customers to deliver admin tools, reporting, LMS and SSO integrations, measurable learning outcomes, and improved activation, retention, and expansion.

Own retention, renewals, churn prevention, and expansion for a high-volume, low-touch B2B SaaS customer segment. Handle cancellation and commercial requests, respond to automated outreach, identify expansion opportunities, maintain Salesforce records and forecasts, and monitor performance metrics. Partner with CX, Billing, and RevOps while improving automation, messaging, and customer engagement processes.

Build and grow the insurance business by creating demand, sourcing and qualifying enterprise opportunities, developing quantified value cases, and leading complex multimillion-dollar technology sales through close. The role coordinates product, engineering, deployment, legal, security, and procurement stakeholders; informs product strategy through customer insights; and develops repeatable sales processes. Candidates need deep insurance domain expertise, enterprise sales experience, technical AI fluency, and a record of independently closing complex engagements.