Top Tech Jobs & Startup Jobs in Chicago, IL

Lead technical project success for enterprise AI infrastructure engagements. Collaborate with engineers, clients, and account leaders to capture requirements, decisions, dependencies, risks, and tradeoffs. Track constraints involving security, compliance, data sovereignty, procurement, and restricted environments. Maintain project visibility, align deliverables with business objectives, resolve issues, support implementation-to-operations handoffs, and identify expansion and renewal opportunities. Translate complex technical concepts for engineering, business, and executive stakeholders.

Design compact connected hardware from concept through prototyping and validation for IoT devices. Optimize for connectivity, energy efficiency, durability, usability, and manufacturability. Collaborate with software and engineering teams, participate in design reviews, and apply current hardware design trends and tools.

Own the full enterprise sales cycle, from prospecting through close, while building executive relationships and creating pipeline. Develop strategic account plans, navigate complex multi-stakeholder deals, translate technical use cases into business outcomes, and close significant opportunities. Partner with founders, product, and engineering teams to shape messaging, pricing, ideal customer profiles, and go-to-market strategy. Help convert early customer wins into repeatable sales motions in a remote, ambiguous, high-growth environment.

Leads company strategy and operations directly with the CEO at an early-stage payments fintech. Owns planning, goals, operating cadence, executive and board materials, cross-functional execution, operational team management, service levels, staffing, escalations, and decision analysis including pricing, corridor economics, partnerships, and market entry. Partners with product on prioritization and market strategy while managing support, product operations, and compliance operations.

Serve as the CEO's strategic and operational right hand at an AI LegalTech startup: prepare executive/board/investor materials, build financial models and decks, contribute litigation expertise to product content, validate LLM-generated analyses, drive cross-functional execution, manage company operations (recruiting, vendor administration, OKRs), represent the CEO, and handle special projects across finance, legal, and partnerships.

Lead product and brand design on a freelance basis: produce developer-ready UX/UI in Figma, build and maintain design systems, craft intuitive user flows, conduct design research, collaborate with PMs and developers, and ensure on-brand visual assets across product and marketing.

Provide bilingual English and Spanish customer support by phone for top-tier client brands. Assist customers, resolve concerns, guide users toward answers, and de-escalate challenging interactions. The role requires a professional demeanor, a quiet workspace, dedicated Windows computer, quality headset, and installation of company security software and a 2FA app. Commitment is 10 hours weekly for approximately 90 days, with flexible scheduling across weekday and weekend project hours.

Lead strategic development for creative briefs and campaigns: uncover audience insights, translate business objectives into briefs, support concept development, assist pitches and new-business strategy, collaborate with creatives and clients, and conduct research to convert data into actionable insights.

Own post-sale customer success for high-impact SaaS accounts, including onboarding, implementation, adoption, renewals, relationship management, issue resolution, QBRs, and customer advocacy. Partner cross-functionally with Sales, Product, Engineering, and Business Operations while developing scalable customer success playbooks, processes, tooling, and engagement strategies. The role requires strategic account management, technical fluency, executive communication, and comfort operating in an early-stage startup.

Onboard new brand customers, coordinate kickoffs, prepare materials, lead platform setup and training, monitor account health, handle support questions and escalations, document customer feedback, and contribute to customer-success playbooks. Build expertise in eCommerce, DTC brand operations, and martech while helping customers adopt OuterSignal and turn data into action.