Top Tech Jobs & Startup Jobs in Chicago, IL

Lead marketing strategy, analytics, and GTM operations for Twilio.org’s Social Impact team. Build investment proposals, ROI models, attribution frameworks, account-tiering logic, automated marketing triggers, executive scorecards, and pipeline-generation programs. Partner with marketing and data science leaders to optimize budgets, campaigns, routing, and commercial performance. Maintain Looker, Tableau, Salesforce, and analytics infrastructure while modernizing SQL-based reporting and data quality processes.

Gather and translate Talent Acquisition requirements into technical specifications, configure and implement recruiting technology solutions, and lead system, integration, and UAT testing. Support platforms including Workday, Eightfold, Greenhouse, LinkedIn, HireRight, and HackerRank. Analyze workflows, troubleshoot issues, manage defects, support audits and SOX controls, document solutions, and provide training and post-implementation support to global TA stakeholders.

Leads Twilio’s external public relations and corporate communications across employer branding, executive communications, customer and partner storytelling, social impact, financial announcements, and media relations. Advises C-suite leaders, develops strategic narratives, secures media coverage, manages executive LinkedIn presence, and collaborates with cross-functional teams and agencies. The role is remote with approximately 20% travel.

Architect and prototype scalable solutions for Twilio’s emerging technologies experimentation team. Lead AI, machine learning, and LLM-driven initiatives; guide technical direction; mentor engineers across the US and India; align prototypes with business goals; and ensure enterprise architecture, scalability, extensibility, and production readiness. The role requires extensive architecture or principal engineering experience, cloud expertise across AWS and Azure, full-stack development knowledge, database expertise, and strong technical leadership.

Lead pricing strategy and execution for enterprise monetization initiatives. Build price optimization models, design dashboards (Tableau/Looker), analyze complex sales and usage data with SQL, and partner with Deal Desk, Sales, and Finance to protect margins and improve revenue realization.

Manage and expand strategic regulated-vertical customer accounts, driving revenue, gross margin, and gross profit growth. Develop account strategies, identify cross-sell and upsell opportunities, lead consultative sales cycles, maintain accurate Salesforce pipelines and forecasts, and present guidance to executives. Partner cross-functionally with product, finance, support, and services teams while building relationships with business and technical leaders.

Lead the CEO’s external communications strategy, including executive messaging, thought leadership, media relations, speaking opportunities, and LinkedIn presence. Partner with PR, social media, marketing, investor relations, legal, brand, and corporate communications teams to align the CEO’s voice with Twilio’s business strategy. The role requires exceptional writing, storytelling, executive judgment, media outreach, cross-functional influence, and the ability to manage high-stakes priorities in a fast-paced environment.

Architects and validates complex, multi-product Twilio solutions for enterprise customers, specializing in trust, identity, security, fraud, and compliance. Leads technical discovery, workshops, demos, proofs of concept, executive presentations, and solution validation. Partners with sales, solutions engineering, product, R&D, and marketing teams to influence roadmaps, create repeatable architecture patterns, communicate customer trends, and serve as a regional technical authority and thought leader.

Provides technical account management and support for strategic Twilio customers. Troubleshoots complex application, network, cloud, and API issues; collaborates with developers, architects, Product, and Engineering teams; files reproducible bug reports; analyzes customer trends; and recommends improvements to reduce downtime and enhance support processes. The role supports Eastern Time hours, manages dedicated accounts, and may require occasional travel and holiday coverage.

Manage Twilio Marketing’s global OPEX budget, including headcount modeling, program spend tracking, forecasting, budget pacing, and fund redeployment. Partner with Accounting, Procurement, and senior Marketing leaders on accruals, purchase orders, financial planning, ROI analysis, and strategic decisions. Modernize FP&A workflows through automation, analytics, and enterprise planning systems while supporting profitable growth.