Top Tech Jobs & Startup Jobs in Chicago, IL

Manage a ~60-account mid-market book to drive adoption, retention, and expansion of Ashby. Deliver product trainings, strategic guidance, and partnership reviews; become a product and domain expert; collaborate cross-functionally to advocate for customers and improve workflows, integrations, and long-term value realization.

Lead Ashby’s GTM Systems & Tools team to architect and manage the revenue tech stack. Own systems strategy, data governance, integrations, and process automation. Mentor a small technical team, run UAT and deployment cycles, partner cross-functionally with Finance, Data, and Engineering, and optimize workflows to scale revenue operations for $100M+ ARR.

Lead end-to-end implementations for mid-market and smaller enterprise customers, managing ~15 concurrent 4–8 week SaaS onboarding projects. Develop and execute implementation plans, align stakeholders, configure multi-module systems, drive change management, advise on best practices, and collaborate across CS, Sales, Product, Engineering, and Ops to ensure rapid time-to-value and strong customer outcomes.

Manage end-to-end implementations for strategic (enterprise) customers, develop and execute implementation plans, configure complex B2B SaaS workflows and integrations, drive change management, advise on best practices, measure outcomes with data, and collaborate cross-functionally to ensure timely, successful onboarding and customer value realization.

Provide day-to-day technical support for a complex B2B SaaS product: troubleshoot integrations and configurations, resolve tickets end-to-end, communicate clearly with varied audiences, escalate appropriately, and contribute to projects that improve support workflows and automation. Participate in a rotating schedule requiring one weekend day.

Build and own Ashby’s Workforce Management function: forecast demand, model capacity scenarios, design global schedules, create dashboards and insights, and partner cross-functionally to balance SLAs, team flexibility, and strategic initiatives. Influence hiring and regional strategy while enabling a tenured, technical Support team to contribute beyond ticket work.

Lead strategy and tactical operations for Customer Success by designing processes, reporting, and tooling to improve customer health, retention, and revenue. Partner cross-functionally to support planning, capacity modeling, onboarding, lifecycle mapping, and change management. Deliver analysis of NRR/GRR, churn, adoption, and health scores to inform CS strategy and operational improvements.

Lead pre-sales scoping and design for enterprise implementations, create and negotiate Statements of Work, ensure smooth Sales-to-Professional Services handoffs, participate in early lifecycle kickoff, refine PS go-to-market motions, and partner with Sales and Solutions Engineering to increase win rates and accelerate time-to-value for enterprise customers.

Lead pre-sales scoping and design for enterprise customers, create Statements of Work, align sales and post-sales teams, participate in handoffs and kickoffs, and improve Professional Services GTM through playbooks and process refinements to increase win rates and speed time-to-value.