Top Tech Jobs & Startup Jobs in Chicago, IL

As Director of Product and Engineering, you will lead the Long Stays product segment, driving strategy, product development, and technical direction, while managing a small team to achieve key commercial metrics and enhance customer experiences.

Serve as senior product counsel embedded with Product, Engineering, Commercial and Compliance to advise on SaaS and regulated fintech products, payments, licensing, AML/BSA/KYC matters, negotiate commercial and partner agreements, support audits and regulatory scrutiny, and build playbooks to enable faster, compliant product delivery.

Senior individual contributor who builds and maintains a division-level design substrate: design system, cross-tribe agents/skills, research engines, and architectural standards. Partners with Staff Designers and the VP on complex cross-tribe problems, encodes design judgment into reusable components/patterns/agents, and drives multi-year design strategy to scale consistent design practice across the company.

Provide senior in-house product and regulatory legal counsel for SaaS and fintech products. Embed with Product and Engineering to advise on payments, embedded finance, licensing, AML/BSA compliance, contracts, supervisory interactions, and cross-border regulatory issues. Draft and negotiate partner, commercial and regulated-services agreements, build playbooks and templates, and support licensing, audits, and scale-up of regulated offerings.

As a Customer Support Analyst, you'll assist clients with technical issues, provide support, and improve usage of Mews solutions, ensuring customer satisfaction in a global environment.

Lead and grow engineering teams for Mews' Front of House products, partnering with Product, Design, and Data to deliver guest recognition, personalization, automation, and connected guest journeys. Set technical direction, improve engineering excellence and operational health, drive cross-tribe collaboration, coach leaders, and translate strategy into measurable business outcomes like increased guest engagement and reduced time-to-serve.

Own net-new mid-market hotel group growth across the Southeast US. Manage full sales cycle from outbound prospecting to close, run high-volume outreach (120+ activities/week), maintain 8-10 active opportunities, multi-thread deals across stakeholders, forecast pipeline, partner with Customer Success for expansion, attend regional industry events, and close 3-4 deals/month averaging €3-5k MRR.