Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end product design for Ashby92s desktop SaaS: own features, consult with engineers and PMs, craft interactions and visuals, write design specs, and build/maintain the design system using heuristics and occasional user research.

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.

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.

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.

Manage a book of ~20 strategic enterprise customers to drive product adoption, retention, and customer health. Become a product and domain expert, tailor configurations and training, multi-thread across stakeholders, and partner with Sales, Product, Marketing, and Ops to scale playbooks and outcomes.

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 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 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 and grow a Support Engineering team that resolves complex product issues, integrations, and data workflows. Define escalation and triage practices, build scalable diagnostics and internal tools, collaborate closely with Engineering and Product, mentor engineers on debugging, logs, and database querying, and create repeatable processes to improve customer outcomes and support efficiency.

Provide technical troubleshooting for customer issues, focusing on API integrations, data flow, and automation via scripting. Collaborate with engineering to escalate and resolve bugs, identify patterns to drive product improvements, maintain support documentation, and enable the Support team through knowledge sharing and process improvements.