Top Tech Jobs & Startup Jobs in Chicago, IL

Lead technical pre-sales for Twilio.org: qualify opportunities, design architectures, run demos and POCs, produce technical proposals, mentor peers, and drive customer adoption across public sector, healthcare, and non-profit customers.

Lead strategy and roadmap for Twilio’s developer and commerce platforms, turning platform engineering into a proactive, self‑service product. Drive developer experience, APIs/SDKs, deployment tooling, observability, and billing/commerce capabilities. Partner with engineering, architecture, security, and stakeholders to prioritize roadmap, measure adoption and reliability, and reduce support burden through developer portals, golden paths, and data-driven KPIs.

Lead and manage a personalized support team for Twilio customers in a remote-first environment. Build customer relationships, drive personalized customer experiences, coordinate occasional in-person meetings, and collaborate across teams while supporting hiring and team development.

Lead strategy and execution for Twilios internal communications, owning high-stakes, sensitive employee messaging, crisis and change communications, and cross-functional counsel with Legal, HR, Security, and Finance. Serve as a strategic partner to communications leadership, ghostwrite for executives, and support broader IC programs, all while ensuring confidentiality, cultural alignment, and clear, empathetic narratives for a global workforce.

Build, operate, and maintain scalable backend services and Kubernetes clusters across AWS and Azure. Contribute production code, Terraform IaC, CI/CD/GitOps workflows, observability, and testing while learning from senior engineers.

The Software Engineer will design, implement, and maintain real-time services for Twilio's Voice Trust team, ensuring robust and high-throughput communication solutions. Responsibilities include gathering requirements, coding, testing, and on-call support in a distributed production environment using Agile methodologies.

Design, build, deploy, and operate resilient, large-scale backend services and Kubernetes clusters across AWS and Azure. Implement GitOps/CI-CD, automate infrastructure with Terraform, ensure observability and reliability, identify technical debt, and mentor junior engineers.

Join Twilio as a Staff Software Engineer to design and build scalable, reliable communication systems. Collaborate with cross-functional teams, mentor engineers, drive technical direction, perform architecture and code reviews, and deliver high-quality production services in a remote-first environment.

Design and deliver partner-focused enablement programs to improve partner-led revenue. Build curricula, lead virtual/in-person training, collaborate cross-functionally, measure enablement impact, and drive partner GTM integration and roadmap alignment.

Lead technical pre-sales activities for Twilio's Digital Sales segment: qualify opportunities, design architectures, run demos and POCs, produce RFP/design docs, and act as trusted technical advisor to customers and account teams. Contribute reusable demos and enablement, solve customer technical challenges, and drive improvements across the solutions engineering community.