Top Tech Jobs & Startup Jobs in Chicago, IL

Design, build, and own AWS infrastructure and automation for a 24/7 SaaS platform. Implement scalable, secure, highly available systems, partner with developers to improve reliability and performance, maintain critical infrastructure, build tooling and processes to reduce toil, participate in weekly on-call rotation and lead RCA and durable fixes.

Acquire and expand regional hotel brands and ownership groups across North America by building executive relationships, leading complex multi-stakeholder sales cycles, creating predictable pipeline through outbound prospecting and events, and collaborating with Marketing, Product, Customer Success, and Enterprise teams to drive new logo ARR and account expansion.

The VP Accounting leads global accounting, focusing on transformation and automation, ensuring compliance with US GAAP, and overseeing financial close processes.

Own full-cycle enterprise sales for Duetto and HotStats, building pipeline, running deals end-to-end with ownership groups and brand stakeholders, delivering tailored demos and proposals, negotiating to close, and partnering with Marketing and Customer Success to grow pipeline and win rates.

Lead and build Duetto's legal function: implement AI-enabled legal tooling, advise on AI/ML product and data/privacy issues, architect scalable commercial contracting and governance, support PE-driven exit readiness and M&A, manage global employment and external counsel, and integrate legal with cross-functional leadership to reduce risk and enable growth.

As a Staff Software Engineer, you’ll lead the design and reliability of Duetto's data lakehouse, evolving data systems using Python and AWS, ensuring data quality, and implementing AI-driven solutions.

Execute product-focused content across channels by turning roadmap updates and feature releases into social-first, creative narratives. Own concepting, briefing, production, and publishing of video and short-form content, manage external agencies, activate user-generated content, and leverage AI-enabled tools to scale output while collaborating closely with product and marketing teams.

Lead enterprise account strategy and ABM to win new logos and expand existing accounts. Build multi-channel programs blending digital and field marketing, design demand funnels and routing processes, enable sales with enterprise assets, and use AI to scale personalization and performance. Deliver measurable pipeline and expansion outcomes.