Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and build Fleetio's product marketing and GTM commercialization function. Create repeatable launch frameworks, positioning, messaging, pricing, sales plays, and enablement. Align Product, Sales, Marketing, Customer Success, and Partners; hire and grow a commercialization team; establish operating rhythms, templates, and metrics to drive adoption, pipeline, and revenue.

Manage end-to-end settlement payment operations including creating and distributing payments per court orders, performing compliance reviews and audits, processing replacements/wires/deposits, preparing tax forms, investigating payment discrepancies with vendors and banks, and safeguarding confidential financial data.

Manage a Mid-Market portfolio (~120 small business accounts, $40-100k ARR), drive renewals and retention, log activities in Salesforce, prepare business reviews, handle contracts/invoicing/quotes, identify upsell opportunities, lead trainings, resolve escalations, and collaborate with internal teams to improve customer adoption and satisfaction.

Lead federal business development for health, readiness, and workforce support: build and manage pipeline, qualify opportunities, support capture and proposals, mentor BD staff, develop account strategies, and present strategic insights to leadership to drive revenue growth.

Lead and execute cross-functional strategic initiatives and M&A integration, translate AI vision into operational deployments, build business cases and ROI tracking, mitigate execution risks, and prepare executive and board-level presentations to report progress and outcomes.

Manage and lead implementations of TeamDynamix ITSM and PPM tools for multiple clients, handling planning, configuration, testing, training, issue resolution, status reporting, and ensuring client satisfaction throughout project lifecycles.

Lead and mentor the platform engineering team to design, build, and maintain scalable infrastructure and tools. Collaborate with product and engineering leadership on technical roadmaps, implement Dev(Sec)Ops best practices (CI/CD, PR reviews, cloud platform management), debug complex issues, and drive hiring and process improvements to support web application infrastructure at scale.

Drive new client acquisition and revenue growth across North America by hunting, full sales-cycle management, upselling existing clients, and closing mid-to-large B2B and venture-backed accounts. Collaborate with product, engineering, marketing, and customer success to improve the platform and sales materials, track and exceed quota, and engage senior stakeholders (CFOs, partners, business owners).

Support co-founders and VP of People with executive logistics, meeting operations, travel coordination, interview and People-team support, culture programming, and ad hoc operational projects. Drive process improvements, vendor coordination, and documentation across a fast-growing healthtech startup.

Support day-to-day follow-up, tracking and documentation of grants, co-investments and programme resources across partners and SNV-led activities. Verify disbursement documentation, monitor budget utilisation, support compliance and audits, track co-investment contributions, strengthen partner capacity, and produce analyses and reports to inform adaptive management and decision-making.