Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and develop a global team managing SaaS renewals and complex contract negotiations. Build scalable renewal processes, improve forecasting and CRM hygiene, partner cross-functionally with Sales, RevOps, Legal, Finance and Product, and translate negotiation outcomes into playbooks to drive retention and commercial growth.

Own and scale Ashby’s paid marketing program across LinkedIn, Meta, Google Search, YouTube, and other channels. Build campaign strategy, creative testing, landing-page experiments, AI-enabled workflows, measurement systems, and budget allocation processes. Partner with sales, lifecycle, ABM, design, content, product marketing, and RevOps to generate qualified pipeline while strengthening the brand. This is a hands-on role requiring deep channel expertise, analytical rigor, creative judgment, and experience in sales-led B2B SaaS.

Lead Ashby’s Americas Mid-Market sales organization, initially managing three sales managers and expanding to four. Responsibilities include hiring and developing managers and account executives, owning regional revenue performance, executing sales plans, building sustainable pipeline coverage, shaping go-to-market strategy, and identifying new market opportunities. The role partners closely with Revenue Operations and Marketing to support significant net ARR growth and expansion of the company’s serviceable market.

Own go-to-market planning and execution for product and feature releases across multiple product lines. Develop messaging, value propositions, demos, videos, blog posts, one-pagers, launch documentation, enablement materials, and customer newsletters. Partner with Product, Engineering, Sales, Solutions Engineering, Customer Success, Support, and RevOps to translate technical features into clear customer value, coordinate launches, and maintain release velocity through scalable systems and automation.

Own product strategy, roadmap, customer research, prioritization, and execution for Ashby’s outbound sourcing, product platform, or AI platform. Partner closely with engineering, customers, and go-to-market teams to deliver high-quality, reusable product capabilities. Drive product vision across a six- to 18-month horizon, manage tradeoffs and technical risks, and improve customer experience through deep research and sound judgment.

Own product strategy, roadmap, customer research, prioritization, and execution for Ashby’s outbound sourcing, product platform, or AI platform. Partner closely with engineering and go-to-market teams to deliver high-quality, reusable product capabilities. The role requires strong product judgment, technical thinking, written communication, business sense, and sustained ownership of impactful customer outcomes.

Own the enterprise product marketing narrative, messaging, content, sales enablement, and go-to-market materials. Research enterprise buying committees, develop segment-specific positioning, support ABM campaigns, create case studies and sales assets, produce ROI and TCO content, and train sales teams. Partner closely with Sales, Solutions Engineering, Customer Success, Marketing, Analyst Relations, and other cross-functional teams to align messaging and support complex enterprise deals.

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.

Drive strategy and operations for the Customer Success organization by improving workflows, onboarding, lifecycle management, reporting, customer health metrics, capacity planning, and renewal processes. Partner with Finance, Sales, Product, RevOps, and Enablement to implement scalable systems, define KPIs, provide data-driven recommendations, and lead adoption of new processes across a fast-growing SaaS business.

Lead Ashby’s Knowledge Management function by setting strategy, governance, quality standards, and success metrics. Manage and develop Knowledge Managers, expand into digital support and localization, and partner cross-functionally with Support, Product, Engineering, Marketing, and Enablement. Co-own the AI Assistant’s structured and generative self-service experiences, establish localization processes, and use analytics, customer feedback, and support trends to prioritize content and improve customer outcomes.