Top Tech Jobs & Startup Jobs in Chicago, IL

Advise as an outbound Playbook Architect: design multi-channel, intent-driven outbound sequences, write copy frameworks and AI prompt logic, and deliver ready-to-launch playbooks that maximize replies and booked meetings. Work asynchronously as an equity-bearing advisor while keeping a full-time job.

Develop and define Retool’s brand voice across websites, campaigns, content, events, and in-product experiences. Partner with design, marketing, product, engineering, and external agencies to translate complex technical concepts into clear, compelling copy. Establish voice and tone systems, maintain brand consistency, experiment with new language, provide creative feedback, and independently manage multiple projects in a fast-paced startup environment.

Lead administration of Microsoft 365, Google Workspace, SaaS applications, Azure identity, and cloud infrastructure in a fully cloud-based organization. Provide Level 2/3 service desk escalation, execute migrations and cybersecurity projects, establish IT service processes, manage assets and vendors, and support onboarding, offboarding, incident response, change management, and M&A initiatives. The role partners with IT leadership and may help build and manage a growing internal technical team.

Own strategy and roadmap for trading APIs or new product initiatives. Use customer feedback, onchain and internal data, and personal DeFi expertise to identify opportunities. Partner with engineering on technical tradeoffs, collaborate with go-to-market teams to drive adoption, and work with the CEO and leadership on product direction. The role requires shipping B2B, API, or infrastructure products with measurable adoption and revenue in a hands-on individual contributor capacity.

Generate qualified top-of-funnel pipeline through inbound lead follow-up and outbound prospecting. Research prospects, identify companies subject to packaging regulations, conduct outreach by phone, email, and LinkedIn, maintain accurate HubSpot CRM records using ZoomInfo data, refine messaging, share sales best practices, and represent the company at industry events. The role is remote with a preference for New York or East Coast candidates, while the location section requests three days per week in the New York City office.

Own a named portfolio of 25–50 Fortune 500 accounts across prospecting, enterprise sales, onboarding, enrollment adoption, expansion, and renewal. Build strategic account plans, manage complex stakeholder relationships, lead RFPs and negotiations, forecast multiple pipelines, and partner with implementation, customer success, marketing, product, and finance teams. Maintain executive-level relationships while driving durable, multi-year revenue growth.

Administers and develops Oracle EPM Cloud and Hyperion financial planning systems. Responsibilities include managing security and user access, maintaining nightly and close processes, troubleshooting integrations, developing enhancements with Groovy and EPM Automate, coordinating patching and regression testing, writing technical specifications and test plans, supporting data governance, analyzing issues, and creating stakeholder training materials. The role collaborates with IT and business teams to deliver reliable, scalable financial systems.

Provide phone, email, and chat support to healthcare clinics using Verse Medical. Resolve ordering, product, shipping, and documentation issues; coordinate escalations with operations, billing, and customer success teams; guide product selection and order workflows; maintain accurate ticket records; update knowledge resources; and advocate for clinics and patients through empathetic, timely communication.

Develop and maintain proposal graphics, templates, layouts, icons, and visual systems for U.S. Government proposals. Translate complex technical concepts into compelling information design, provide rapid support during proposal deadlines, establish visual standards, update branding guidelines, and recommend improvements to corporate materials. Collaborate with proposal managers, writers, subject-matter experts, and leadership while explaining design decisions and ensuring visual consistency.

Manage approximately 15 digital banking clients across the Western U.S., driving retention, renewals, revenue growth, and product expansion. Build executive relationships, conduct business reviews, align digital strategies with client outcomes, present proposals, negotiate contracts, and promote multi-product adoption. Collaborate with sales, marketing, product, and implementation teams to support client success. Represent the company at trade shows, conferences, and client events.