Top Tech Jobs & Startup Jobs in Chicago, IL

Own the enterprise pre-sales technical sales cycle, including discovery, demos, solution architecture, proofs of concept, and implementation support. Partner with Account Executives, Sales Leadership, Customer Success, Product, and onboarding teams to drive technical wins and adoption. Develop scalable technical assets, playbooks, lab environments, and sales processes while advising on RFPs, customer requirements, product gaps, and enterprise IT operations.

Design new features and enhancements for PSA and Service Desk software products from discovery through delivery. Create user flows, wireframes, and high-fidelity UI designs; conduct user research and usability testing; collaborate with Product Managers, Engineers, Marketing, and other designers; maintain and expand the design system; and deliver intuitive, polished customer experiences in an agile, remote environment.

Own the full technical pre-sales cycle for enterprise partners, channel customers, MSPs, and B2B SaaS accounts. Responsibilities include discovery, demonstrations, architecture, proofs of concept, technical RFP/RFI support, customer engagements, and implementation guidance. Partner with account executives, product, training, and customer success teams; represent the company at industry events; surface product feedback; and build scalable technical assets, playbooks, tools, and processes. The role requires strong enterprise IT operations expertise, technical communication, and approximately 50% travel.