Top Tech Jobs & Startup Jobs in Chicago, IL

Design, deliver, and evolve role-based training and change management programs for transit agency customers. Lead remote and onsite training, create scalable learning content (videos, KB articles, webinars), enable internal teams, leverage AI tools for content, and measure impact via adoption and training satisfaction metrics.

Lead end-to-end SaaS implementation projects for transit agencies, manage timelines and stakeholders, perform data migration and integrations (GTFS, AVL, GPS), conduct testing and training, drive adoption, provide technical troubleshooting, and identify process improvements while collaborating with Sales, Product, Engineering, and Support.

Design and maintain real-time vehicle-tracking, map-matching, ETA prediction, and disruption-detection systems. Build and scale real-time data pipelines, cloud backend services, and APIs. Develop infrastructure for algorithm validation and shadow testing, collaborate across product and design to prototype and deliver end-to-end features, and apply modern engineering practices through code reviews, pairing, and documentation to ensure reliable production systems.

Build and maintain scalable, cloud-native full‑stack features and services. Collaborate with Product and Design to prototype, deliver, and document solutions. Work across backend and frontend, apply modern engineering practices, mentor teammates, and own product domains to improve transit operations.

Lead and scale Swiftly's communications function across brand, content, PR, social, proposals, and executive comms. Build narrative systems, measurement, crisis and investor communications, stakeholder engagement with transit agencies and public sector partners, and partner closely with sales, product, and demand generation to drive reputation and revenue.

The Senior Software Engineer will design, build, and maintain solutions for transit agencies, focusing on IoT devices and cloud services, ensuring reliable communication and device management.

Lead a cross-functional product team to develop real-time operational tools for transit agencies, ensuring technical guidance and team support towards impactful solutions.

This posting builds a talent community for a future Senior Account Manager role. Candidates should have account management experience (ideally in SaaS, public sector, or transit tech), be mission-driven about mobility/sustainability, and be willing to join a distributed team and attend occasional in-person offsites. Submitting interest puts you first in line when a role opens.

Lead and develop a team of 5 SMB Account Executives selling Swiftly's transit SaaS platform to small and mid-size public transit agencies. Own hiring, coaching, pipeline strategy, forecasting in Salesforce, and enforce SPICED methodology. Support discovery, demos, procurement navigation, and cross-functional alignment while driving team quota attainment and attending conferences/offsites.