Top Tech Jobs & Startup Jobs in Chicago, IL

Lead Ashby’s global B2B SaaS Support organization, currently comprising two Heads, five Managers, and approximately 60 technical contributors, with plans to nearly double the team. Own global support strategy, 24/7 coverage, automation, SLAs, queue management, escalations, training, and continuous improvement. Partner with Customer Success, Sales, Product, Engineering, and Operations to improve customer outcomes, resolve recurring issues, and scale support processes, quality, and efficiency.

Manage a pooled book of SMB customers as their primary contact, providing onboarding assistance, email and call support, troubleshooting, and long-term success guidance. Create onboarding materials, documentation, webinars, and retention practices. Own cross-functional projects that improve customer engagement and internal operations while becoming a product expert and solving complex customer challenges.

Lead and coach a team of enterprise Customer Success Managers serving complex B2B SaaS customers. Improve customer journey processes, adoption, optimization, retention, and team performance while balancing scalable systems with bespoke enterprise experiences. Partner cross-functionally with Product, Support, Sales, RevOps, Implementation, and Contract Management. Act as a technical resource, advocate for the team, and voice of the customer while driving data-informed operational improvements.

Own and scale Ashby’s demo environment system by customizing templates, generating realistic data, creating vertical-specific demos, and standing up trial and sandbox environments. Ensure new releases are demo-ready, document system usage, and enable go-to-market teams. The role requires hands-on work with JSON, APIs, data preparation, automation, internal tooling, and close collaboration with Engineering, Product, and Solutions Engineering.

Manage annual renewals and month-to-month subscriptions for startup customers across the Americas. Lead pricing and contract negotiations, answer contract questions, generate order forms, maintain CRM records, and build customer trust. Collaborate with Sales and Customer Success to drive retention, expansion, and customer satisfaction while identifying growth opportunities. The role requires strong communication, empathy, attention to detail, autonomy, adaptability, and comfort managing a high volume of accounts remotely.

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.

Lead customer-facing technical engagements implementing Ashby integrations with enterprise HCM platforms. Define requirements, design and troubleshoot integration solutions, manage project plans and milestones, advise customers on best practices, support change management, and coordinate with Product, Engineering, Customer Success, Sales, and Implementation teams. The role also contributes to process improvement, pre-sales support, customer coaching, and scalable solutions for strategic customers.

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.

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.

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.