Top Tech Jobs & Startup Jobs in Chicago, IL

Leads Year 15 LIHTC investment dispositions, investor exits, partnership restructurings, and ownership transfers. Analyzes partnership agreements, entity structures, tax impacts, valuations, waterfalls, NPV, and financial models. Coordinates due diligence and negotiations with investors, developers, syndicators, legal counsel, and internal teams while managing transaction risks and supporting affordable housing preservation. Prepares investment committee materials and recommendations for senior leadership.

Leads the development, standardization, delivery, and continuous improvement of sUAS training programs. Oversees instructional designers and curriculum developers, establishes training architecture and standards, evaluates instructors, manages curriculum lifecycle, supports product training launches, conducts audits and validations, and delivers technical and operational instruction across classroom, manufacturing, flight-line, customer, and field environments.

The Volunteer Digital Marketing Manager will manage SEO, AEO, content strategy, email marketing, and analytics to enhance the online presence of the Humane Choices Foundation, aiming to improve discoverability and engagement.

Lead end-to-end product design for DubClub’s mobile marketplace serving sports betting creators and fans. Own discovery, information architecture, user flows, prototyping, visual design, research, usability testing, and implementation review. Shape fan subscription and engagement journeys, build creator business tools, establish consistent design patterns, and influence product priorities. Collaborate closely with Product, Engineering, Creator Success, users, and leadership while remaining hands-on and guiding overall product quality.

Six-month engineering internship building production backend services and AI pipelines. Design SQL schemas (PostgreSQL), implement SaaS integrations (REST APIs, webhooks), work with embeddings, transformer models and vector databases, build end-to-end data processing pipelines, and contribute to code reviews and architecture discussions.

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.

Supports compensation programs, salary structures, job leveling, market pricing, pay equity, incentive plans, and regulatory compliance. Partners with HRBPs, Recruiting, and business leaders on pay recommendations, job classifications, salary surveys, and compensation analytics. Leads compensation technology improvements, prepares reports and dashboards, and contributes to broader Total Rewards and HR operations initiatives.

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.