Top Tech Jobs & Startup Jobs in Chicago, IL

Configure and demonstrate Legion’s workforce management platform to prospective enterprise customers. Lead presales discovery, product demonstrations, proof-of-concept engagements, RFP responses, and business justification. Partner with Enterprise Sales to understand customer business and technical needs, communicate platform value, identify risks, and overcome implementation obstacles. Maintain demo environments, contribute to competitive differentiation, and attend field events as needed.

Prospect into strategic accounts, qualify marketing and partner-generated leads, schedule sales meetings, generate opportunities, and achieve activity quotas. The representative researches contacts, conducts cold calls and email outreach, communicates the platform’s value proposition, supports virtual and in-person event attendance, maintains product knowledge, and accurately records lead and activity history in Salesforce. The role requires strong communication, organization, collaboration, business acumen, and experience selling SaaS to large organizations.

Lead the end-to-end development of agentic AI products for workforce management, from operational research and agent definition through prototyping, evaluation, enterprise deployment, and commercialization. Define human-in-the-loop controls, tools, escalation rules, specifications, and release criteria. Build prototypes, prompts, evaluation sets, and code contributions while diagnosing model and system failures. Partner with enterprise design customers, engineering, AI Lab, executives, and go-to-market teams to deliver reliable, compliant products.

Configure and demonstrate workforce management software for prospective customers in a presales capacity. Support enterprise sales through discovery meetings, product demonstrations, proof-of-concept presentations, technical RFP responses, and business justification. Diagnose customer labor-management challenges, tailor solution presentations, identify risks, and address technical obstacles. Maintain demo environments, participate in competitive differentiation, and attend occasional field events. Requires strong software presales, technical, communication, presentation, project management, and customer-facing skills.

Sources, develops, and closes new enterprise business across North America. The role develops go-to-market and account strategies, builds executive relationships, manages the full sales lifecycle, creates ROI-based business cases, exceeds revenue quotas, and maintains accurate Salesforce pipeline and forecast data. Candidates need enterprise SaaS sales experience, a record of closing large new-business deals, strong negotiation and communication skills, and preferably experience selling workforce management or human capital management solutions.

The Chief Architect will lead the technical direction for Legion's Workforce Management platform, focusing on architecture decisions, AI systems, and scalable software solutions. Responsibilities include hands-on coding, technical leadership, and ensuring systems meet enterprise standards for performance and security.

Provide broad corporate legal support: draft, review, and negotiate commercial and SaaS agreements; advise cross-functional teams on compliance; develop policies; conduct legal research; coordinate with outside counsel; assist with corporate governance, entity matters, and special projects to mitigate risk and support business objectives.