Top Tech Jobs & Startup Jobs in Chicago, IL

Own relationships with employee benefits brokers and consultants to expand BetterHelp’s Enterprise business. Build engagement strategies, generate partner-sourced pipeline, support sales opportunities, deliver enablement and presentations, and provide market insights. Collaborate with Sales, Partnerships, Marketing, Product, and Operations to strengthen partner relationships, improve go-to-market execution, and drive qualified business opportunities.

Own the full new-business sales cycle across an SMB and Mid-Market territory, including prospecting, pipeline development, discovery, presentations, negotiations, contracting, and closing. Build relationships with employers, brokers, consultants, and partners in the HR and Benefits ecosystem. Deliver quota, maintain forecast accuracy, develop territory strategy, and collaborate cross-functionally to expand BetterHelp’s enterprise sales business.

Build and maintain scalable full-stack web applications using PHP, Laravel, React, Next.js, SQL, and related technologies. Own features from design through deployment and monitoring, develop APIs, optimize databases and legacy systems, troubleshoot performance issues, and contribute to code quality, security, and engineering practices. Collaborate cross-functionally in an agile, continuous-deployment environment while using AI-assisted tools responsibly.

Associate Director and Corporate Counsel will lead international legal support for BetterHelp’s expansion across Europe and other markets. Responsibilities include advising on contracts, privacy and GDPR, telehealth regulation, marketing and consumer protection, employment matters, litigation, compliance, government inquiries, and market launches. The role negotiates agreements, manages outside counsel, supports privacy operations, and partners with product, marketing, and business teams. Remote work is available, with travel to San Jose up to three times annually plus one company-wide offsite.

Design, deploy, and maintain reliable production and corporate systems; manage configuration, security, and core infrastructure; participate in on-call incident response; build automation, CI/CD pipelines, and Infrastructure-as-Code; monitor systems and develop tools to improve reliability and availability.

Design, productionize, and scale machine learning and optimization models, pipelines, libraries, and deployment platforms. Partner with data scientists, engineers, product managers, and business stakeholders to deliver ML capabilities, personalization systems, and reusable end-to-end workflows. Establish ML engineering best practices, troubleshoot data pipelines, mentor junior professionals, and help define BetterHelp’s ML platform strategy.

Lead BetterHelp’s organic brand and distribution strategy across social, creators, partnerships, community, long-form content, PR amplification, and emerging channels. Build audience-first channel strategies, creator relationships, cultural activations, international distribution, measurement frameworks, compliance systems, and AI-assisted workflows. Manage and mentor a growing team, budgets, agencies, and partners while connecting organic, earned, and paid distribution to expand brand relevance and reach.

Provides corporate legal counsel for BetterHelp’s B2B and direct-to-consumer operations. Drafts and negotiates enterprise, partnership, marketing, affiliate, reseller, referral, vendor, and healthcare agreements. Advises on HIPAA, FTC, privacy, information security, telehealth, healthcare, and advertising regulations. Partners with sales, product, marketing, engineering, compliance, and operations to operationalize agreements and support digital health partnerships.

The Staff ML/AI Platform Engineer will design, prototype and deploy AI/ML models, optimize pipelines, mentor junior engineers, and collaborate closely with other teams to develop machine learning solutions.

Lead analytics and insights for the CFO and exec team: produce executive-ready analyses, design scalable analytics infrastructure, leverage AI to accelerate workflows, partner cross-functionally to drive strategy and execution, and manage multiple high-impact initiatives.