Top Tech Jobs & Startup Jobs in Chicago, IL

Own the end-to-end product strategy, roadmap, monetization, analytics, and experimentation for a consumer VPN business. Grow subscription revenue through pricing, paywalls, trials, retention, and billing improvements while launching a free ad-supported tier. Manage hybrid monetization, app-store compliance, acquisition economics, P&L performance, and cross-functional delivery across engineering, design, data, monetization, legal, and user acquisition.

Own a portfolio of mobile apps across wellness, budgeting, and future categories. Lead discovery, validation, experimentation, monetization, pricing, subscriptions, advertising, data-sharing experiences, and product lifecycle decisions. Allocate investment across apps, lead a cross-functional squad, collaborate with design and engineering, use analytics and user research, and determine whether products should scale, enter maintenance, or sunset. Apply AI tools to accelerate research, prototyping, specifications, and analysis.

Lead hands-on development of user-facing Android and iOS applications, taking ownership from design through production release. Build maintainable, well-tested features, optimize performance, debug unfamiliar systems, and manage app-store publishing. Collaborate with product, design, backend, and users in an agile, remote environment. Use AI coding agents responsibly to accelerate implementation, testing, reviews, infrastructure work, and incident investigation.

Build, test, release, and maintain native Android and iOS applications across a portfolio of consumer mobile products. Use Kotlin, Swift, modern mobile frameworks, automated testing, analytics, experimentation, and AI coding agents to deliver high-quality software. Collaborate with product, design, marketing, operations, and engineering teams, measure user impact, manage app-store releases, and adapt across codebases and product pods.

Lead engineering ownership of an acquired consumer VPN product from due diligence through integration, stabilization, and growth. Manage and coach engineers while remaining hands-on with Kotlin, Swift, Go, architecture, operations, security, and production incidents. Establish testing, CI/CD, infrastructure, documentation, and compliance practices; partner with product, corporate development, marketing, and operations; and create a repeatable engineering playbook for future acquisitions.

Own and scale production backend systems using Ruby on Rails, PostgreSQL, Sidekiq, APIs, microservices, queues, and distributed architectures. Diagnose and improve reliability, security, performance, observability, testing, and deployment practices. Integrate third-party services, collaborate with product, data, design, and frontend teams, and modernize inherited systems while maintaining delivery speed. The role requires strong production ownership, pragmatic technical judgment, and comfort working remotely in a fast-moving startup.

Own and operate a globally distributed VPN network, AWS control plane, backend infrastructure, and infrastructure-as-code tooling. Improve reliability, security, automation, observability, CI/CD, deployment safety, and cost efficiency across multiple providers. Troubleshoot production incidents, participate in 24/7 on-call, manage networking and VPN technologies, and replace manual operational processes with tested automation. Partner with engineering and product teams while ensuring high uptime, connection success, performance, and compliance.

Own and evolve the backend and Go networking engine for a consumer VPN product. Responsibilities include stabilizing production systems, developing account, subscription, server-selection, and WireGuard APIs, integrating payment and analytics platforms, improving security, testing, observability, documentation, and CI/CD, and collaborating with mobile, infrastructure, product, and operations teams.

Own Android and iOS mobile development for a large consumer VPN product. Inherit and modernize existing codebases, integrate native VPN networking libraries, improve security, testing, CI/CD, release management, and app-store compliance. Collaborate with product, design, backend, DevOps, and marketing teams to deliver reliable user-facing features. Diagnose networking issues across mobile and Go components, optimize connection performance, and use AI coding agents responsibly.

Own and optimize ad monetization and yield strategy across Mode’s mobile app portfolio. Responsibilities include managing mediation, waterfalls, pricing floors, ad placements, demand partners, creative quality, and user segmentation; analyzing ARPDAU, eCPM, fill rate, and LTV; conducting experiments; and partnering with product, engineering, data, growth, and advertising teams to increase revenue.