Top Tech Jobs & Startup Jobs in Chicago, IL

Own and optimize sales tech stack and CRM, manage pricing sheets and deal pricing accuracy, ensure correct billing handoffs, maintain data hygiene, build operational reporting and dashboards, monitor pipeline health, and improve sales processes in partnership with Sales, Finance, and Customer Success.

The Senior AI Engineer at RegScale designs and operates AI systems, ensuring reliability and performance while overseeing the data pipeline and compliance integration, alongside improving AI capabilities across the engineering organization.

Design, build, and own AWS infrastructure and automation for a 24/7 SaaS platform. Implement scalable, secure, highly available systems, partner with developers to improve reliability and performance, maintain critical infrastructure, build tooling and processes to reduce toil, participate in weekly on-call rotation and lead RCA and durable fixes.

Serve as the compliance SME for HSA, FSA, and HRA products: review marketing and customer content, lead compliance risk assessments (including AI tools), advise product and ops teams on transaction and regulatory issues, monitor regulatory changes, support escalations and audits, and recommend controls and remediation for identified risks.

Lead and scale a unified Revenue Operations function across Sales, Marketing, and Customer Success. Own GTM strategy, forecasting, territory design, quota and compensation, deal desk, GTM systems (Salesforce/HubSpot), quote-to-cash automation, and cross-functional enablement. Build and mentor a global ops team, deliver pipeline and performance insights, and drive change management to improve revenue growth, productivity, and commercial execution.

Manage and grow client relationships in the eClinical market, drive new business and revenue, prospect and penetrate pharma/biotech/MedTech accounts, develop territory and account strategies, collaborate with service delivery and cross-functional teams, use CRM (Salesforce) for pipeline management, and travel 40–60% to meet clients.

Support Bantam Communications' public affairs teams by conducting research, drafting and editing communications, coordinating with clients and partners, tracking tasks and timelines, and using AI tools to draft and polish materials while learning across campaign, advocacy, research, and communications work.

Senior Strategy & Ops generalist focused initially on Billing: optimize collections and cash conversion, build predictive analytics and underwriting, vet AI vendor solutions, redesign payment conversion processes, and potentially manage Billing Account Managers to improve profitability while preserving customer experience.

Lead a small team to design, run, and measure scaled GTM customer programs. Own sprint cadence, telemetry/scoreboard, productized GTM assets, cross-functional coordination, and coaching to drive adoption and revenue impact.

Lead Program Management for K12 domestic group travel: manage Program Managers, ensure pricing, itineraries, and operational readiness; drive cross-functional collaboration, process improvement, automation, reporting, and profitability while supporting workforce planning and customer/stakeholder satisfaction.