Top Tech Jobs & Startup Jobs in Chicago, IL

Manage renewals and subscriptions for startup (≤100 employees) customers across the Americas. Lead pricing and negotiation discussions, execute renewal processes, maintain contracts and CRM records, generate order forms, collaborate with Sales and Customer Success, and identify expansion opportunities to drive retention and growth.

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 and build HR operations and systems at an early-stage company: manage HR systems, reporting and dashboards, process improvement, performance management, compliance, automation/AI initiatives, partner with Product and customers, and document/communicate change across the organization.

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.

Sell Ashby’s talent acquisition platform to high-growth startups (≤100 employees). Manage inbound and outbound pipeline, run demos, source meetings via outbound prospecting, hit stretch quotas, and maintain detailed CRM and sales operations.

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.