Top Tech Jobs & Startup Jobs in Chicago, IL

Lead the vision, strategy, roadmap, and execution of a compliance platform encoding more than 200 statutory leave and accommodation laws. Manage product managers and compliance experts, translate regulations into scalable features, maintain content accuracy, and apply AI and automation responsibly. Partner with Legal, Engineering, Design, Sales, and Customer Experience to deliver compliant products, support go-to-market readiness, measure outcomes, represent customer needs, and identify regulatory risks and opportunities.

Lead and scale the mid-market sales organization for a high-growth SaaS HR platform. Develop and execute sales strategies, manage and coach account executives and sales leaders, drive pipeline management and forecasting, partner cross-functionally to expand accounts, and represent the company at industry events to meet revenue targets.

Design, build, and deploy scalable AI/ML models (especially NLP and predictive models), implement MLOps and data pipelines, optimize model performance, research prototypes, ensure ethical and compliant AI, and collaborate with product, engineering, and data teams to embed AI into the leave management platform.

Design, develop, and run sales enablement programs: own Highspot content, build/playbook and onboarding, analyze Gong calls to create coaching materials, run trainings, track ramp and certifications, partner with sales leaders, and support kickoffs and QBRs while maintaining compliance.

Executive leader owning sales operations strategy, systems, and processes: forecasting, territory and compensation design, sales technology, analytics, team building, and cross-functional alignment to improve revenue predictability, sales productivity, and reduce time-to-close.

Lead and scale Account Management to drive renewals, upsell, cross-sell, and account expansion across Mid Market, enterprise, and TPA customers. Set quotas and KPIs, manage forecasting and CRM hygiene, coach on MEDDPICC, negotiate high-stakes renewals, and partner with Customer Success, Product, and Marketing to convert adoption into measurable growth revenue.

Own a core product area end-to-end: set strategy and roadmap, lead discovery and specs, partner with engineering and design to ship, instrument and track post-launch metrics, translate customer insights into prioritized product work, and present outcomes to executive leadership while maintaining security/compliance.

Lead and develop a team of Enterprise Account Executives to hit revenue targets in a B2B SaaS environment. Manage pipeline, forecasting, deal coaching, hiring, and sales process adoption (MEDDPICC). Partner with Marketing, Sales Ops, Customer Success, and Product to optimize GTM strategy and maintain CRM and compliance controls.