Top Tech Jobs & Startup Jobs in Chicago, IL

Partner with R&D product leaders to prioritize investments, build ROI-driven financial frameworks, lead forecasting and scenario planning, develop flexible financial models for portfolio optimization and M&A analysis, synthesize insights for executives, and manage a team of 3–4 financial analysts supporting Engagement and Channel products.

Lead the strategic design vision for Twilio Email and SendGrid, defining end-to-end workflows, cross-channel UX harmonization, observability and telemetry patterns, scalable design system primitives, and mentoring designers while partnering with product and engineering leaders to shape long-term platform roadmaps.

As a Staff Machine Learning Engineer at Twilio, you will build and maintain data pipelines and ML infrastructure, ensuring high-quality data and model performance while collaborating with product and security teams.

Lead Trust Hub (KYC) product initiatives end-to-end: define vision and roadmap, drive cross-functional delivery, translate customer needs into requirements, set success metrics, run data-driven reviews, and mentor junior PMs to ensure compliant, developer-friendly onboarding experiences.

Partner with R&D, Product, and Engineering as the autonomous finance lead for cloud infrastructure costs. Build dynamic driver-based forecasts and financial models, perform deep-dive variance analyses, identify cost-containment opportunities, track vendor and cloud spend, ensure correct accounting classifications, drive automation and process simplification, and communicate complex cloud cost structures to non-financial stakeholders.

As a Software Engineer on the Segment team, you'll design, build, and scale APIs for customer data solutions, collaborate with cross-functional teams, and improve system reliability through coding and troubleshooting.

Lead and grow enterprise Communications platform accounts (Financial Services and Health & Life Sciences). Develop account strategy, run consultative sales cycles, manage forecasts and pipeline in Salesforce, collaborate cross-functionally, and deliver revenue and gross profit results.

Drive net-new customer acquisition and close deals within self-service accounts. Understand customers' business and technical needs, design Twilio API-based communications solutions, collaborate cross-functionally, prioritize multiple deals, and help build processes and playbooks to grow revenue and ensure customer satisfaction.

Qualify leads, acquire new self-service customers across nonprofit and social-impact sectors, design technical solutions using Twilio's communications APIs, manage full sales cycles and pipeline in Salesforce, execute automation strategies to scale customers while preventing churn, collaborate cross-functionally, and communicate technical and financial details clearly to drive revenue and customer satisfaction.

This role involves owning PLG analytics, translating business needs into technical solutions, building strategic partnerships, and synthesizing complex data for insights.