Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Perform outbound B2B cold calls to qualify leads and set demo appointments for Account Executives. Follow and adapt outreach scripts, log activity in the CRM, and collaborate with Sales and Marketing to improve outreach. Work EST hours remotely, meet quotas, and support expansion into multiple international markets.

Leads integrated global go-to-market strategy and marketing planning for Marathon releases, seasons, and franchise moments. Develops audience-led acquisition, reactivation, retention, and engagement plans; coordinates cross-functional and regional teams; manages GTM operating rhythms, risks, budgets, agencies, and paid media. Establishes KPIs and measurement plans, evaluates campaign performance, and uses player, market, and business insights to optimize marketing investments and future initiatives.