Top Tech Jobs & Startup Jobs in Chicago, IL

Conduct hands-on manual testing, reproduce customer-reported bugs, assess feature quality, coordinate testing for major launches, and write Playwright end-to-end tests. Collaborate closely with engineers and stakeholders, determine appropriate test coverage, expand automation, and develop strong product judgment while learning Ashby’s product and technical architecture.

Own and scale Ashby's global Total Rewards function across compensation, equity, benefits, and perks. Build compensation infrastructure, leveling, bands, benchmarking, review processes, equity administration, benefits strategy, vendor management, and scalable systems. Partner with Finance, Talent Acquisition, Legal, People Operations, and leaders on workforce planning, offers, promotions, and complex rewards decisions. The role begins as a hands-on individual contributor and is expected to evolve into people management.

Own Ashby’s overarching company and brand narrative, messaging framework, and annual keynote. Conduct customer, market, and sales research; translate insights into differentiated messaging; create startup and lower mid-market content and enablement; align narratives across segments; and partner closely with the CEO, product marketing, sales, partnerships, product, and engineering teams. Initially an individual contributor, the role will later build and lead a team.

Lead and scale a Support Engineering function for Ashby across the Americas. Own vision, operating model, escalation/triage standards, reporting, tooling, and cross-functional feedback with Product and Engineering. Manage a Support Engineering Manager, drive hiring and career paths, and use data to reduce recurring technical friction while balancing immediate customer resolution with durable product improvements.

Own marketing operations for a multi-product portfolio: implement tracking and attribution in HubSpot, build dashboards and reports, design marketing automation, manage data governance and compliance (GDPR/CCPA), collaborate cross-functionally with RevOps, and recommend/evaluate marketing technologies.

Own Ashby’s marketing operations foundation across campaign tracking, attribution, automation, dashboards, reporting, data governance, segmentation, privacy compliance, and marketing technology. Partner with Marketing, Revenue Operations, and Business Systems to implement initiatives, improve pipeline and CAC measurement, maintain data integrity, document processes, train users, and evaluate tools. This is a hands-on individual contributor role requiring technical systems ownership, analytical problem-solving, and strategic KPI development.

Lead Ashby's AMER community-led growth efforts through curated customer and partner events, TA leader relationship building, product education, demos, advocacy programs, and industry engagement. The role requires deep talent acquisition expertise, Ashby product knowledge, strong writing and facilitation skills, hospitality, travel, and the ability to experiment with community formats and enablement programs.

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 ~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 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.