Top Tech Jobs & Startup Jobs in Chicago, IL

Leads FreshBooks’ Payments and Financial Services business, owning operating cadence, TPV and revenue forecasting, P&L impact, pricing, partner relationships, payment operations, risk, compliance, and strategic initiatives. Drives execution across Product, Engineering, Marketing, Sales, Operations, Support, and Risk while managing processors, networks, BNPL partners, payouts, reconciliation, PayFac controls, and customer pricing. Develops near-term strategy, supports annual planning, and delivers executive recommendations and measurable commercial outcomes.

Own and grow Trek, Electra, and Bontrager sales across a designated territory by managing retailer relationships, forecasting, prospecting, and pipeline activity. Advise dealers on merchandising, inventory, staffing, profitability, and continuous improvement. Recruit and onboard new retail partners, deliver product and sales training, monitor market trends, enforce brand standards, and represent Trek at events. The role requires regular in-person travel around the Hartford/Boston area, including occasional overnight trips.

Own the full sales cycle for new healthcare provider accounts, including prospecting, discovery, product demonstrations, negotiation, and closing. Build and manage pipeline, maintain accurate forecasts, meet revenue targets, and develop business cases for complex healthcare purchases. Collaborate with marketing, sales development, and product teams, attend industry events, and provide market feedback. The role is remote and focuses on selling to musculoskeletal provider groups and specialty clinics.

Lead product-focused data science and machine learning initiatives, including exploratory analysis, production model development, evaluation frameworks, generative AI, graph-based machine learning, recommendation systems, and personalization. Collaborate with engineering, product, and business teams to deliver high-impact solutions, influence strategy, and communicate insights to technical and non-technical stakeholders. The hybrid role requires four days per week in the Greater Boston area.

Coordinates influencer relations programs, including creator identification, outreach, gifting, contracts, campaign logistics, reporting, database maintenance, and payment administration. Builds relationships with creators, stylists, agents, and internal partners while supporting global campaigns, retailer activations, and community engagement. Requires strong organization, communication, writing, social media interest, and 1–3 years of relevant experience.

Own daily social media for Pitchbox’s SaaS products across X, Facebook, Instagram, LinkedIn, and Reddit. Create and publish copy, short-form videos, and repurposed content; manage comments, replies, and DMs; participate in industry conversations; test formats and hooks; monitor trends; and report on reach, engagement, traffic, and signups using analytics and UTM links.

Own Civic Marketplace’s commercial and operational engine as a hands-on, near-cofounder-level leader. Responsibilities include connecting product, operations, and commercial teams; managing dashboards, reporting, and performance; owning P&L and business outcomes; developing the business model; setting priorities; building public-sector customer trust; and hiring and coaching leaders. The role requires strong quantitative judgment, early-stage operating experience, pragmatism, and comfort with ambiguity.

General application for future opportunities at a remote open-source consulting company. Potential work includes software engineering, scientific computing, AI/ML, data engineering, DevOps, developer tooling, frontend development, technical writing, design, and community engagement. Quansight welcomes professional, research, educational, personal-project, and open-source experience, including early-career and internship interest.

Lead complex, multi-phase enterprise SaaS implementations for strategic customers. Manage project scope, schedules, budgets, resources, risks, change control, stakeholder communication, and executive reporting. Partner with solution architects, engineering, and technical consultants on integrations, configurations, technical risks, and deployment readiness. Mentor project managers and improve professional services delivery methodologies, tools, and technical playbooks.

Lead the architecture and evolution of a Flutter app across iOS and Android. Build interactive trading features, design systems, performance improvements, automated testing, analytics, feature flags, and resilient API integrations. Mentor engineers, contribute to code reviews and design documentation, support release and QA processes, and participate in mobile on-call rotations. The role partners closely with Product, Growth, Design, Backend, and Platform teams.