Top Tech Jobs & Startup Jobs in Chicago, IL

Leads enterprise AI, data, application, and product strategy; oversees AI adoption, governance, architecture, software development, enterprise applications, and data strategy. Partners with executives to prioritize technology investments, deliver measurable business outcomes, establish standards, manage portfolios, and guide organizational change. Leads teams through coaching, hiring, budgeting, performance management, and workforce planning.

Leads UDig’s Strategy and Design practice, shaping client business and product strategy, experience strategy, research, and design delivery. The role oversees key accounts, develops a large distributed team, grows offerings and client relationships, and establishes AI-first methods. Responsibilities include executive client engagement, product roadmaps, operating model modernization, quality oversight, hiring and coaching, utilization management, proposals, pricing, pitches, and practice reputation-building. Regular client travel is expected.

Drive client adoption, implementation, and delivery of Shibumi SaaS solutions. Configure applications to meet business requirements, translate client artifacts into solution structures, coach and train customers and partners, support pre-sales demonstrations and RFX responses, and manage multiple engagements. Use AI tools responsibly for analysis and productivity while protecting confidential client data.

Coordinate and confirm appointments between clients and security professionals; answer calls, emails, and messages; manage scheduling software and availability; send reminders and follow-ups; maintain accurate records; protect confidential client information; provide professional customer service.

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.