Top Tech Jobs & Startup Jobs in Chicago, IL

Lead strategy and execution for AI-powered Customer Success Services, overseeing Gainsight and related platforms, customer community strategy, customer intelligence, automation, digital engagement, platform governance, and a team to scale adoption, retention, and operational efficiency across the customer lifecycle.

Lead and scale Recast's Customer Enablement Program: design curriculum, deliver trainings and webinars, build enablement content libraries, deploy enablement platform, and collaborate with Customer Success, Support, and Product to improve product adoption and resolve recurring customer issues.

Develop and execute a data-driven SEO strategy to increase organic, local visibility and generate qualified client inquiries across Virginia. Perform technical audits, keyword and intent research, on-page and local SEO, Google Business Profile management, link building, AI-driven SEO optimization, CRO-focused content and landing pages, and track performance using GA4, Search Console, Looker Studio, and SEO tools. Collaborate with marketing and web development to implement Webflow optimizations and report on acquisition and ROI.

Lead end-to-end enterprise sales to state and local agencies: build pipeline, manage long (12–24 month) deals, navigate procurement/RFPs and federal funding, design pricing and packaging, and scale a sales motion while personally closing initial statewide engagements.

Design and open-source LLM observability libraries, pipelines, and APIs; collaborate with the OSS community; prototype LLM techniques; integrate tooling into Arize's platform to improve debugging, evaluation, and metrics; and produce docs, tutorials, and evangelism to grow the LLM evaluation community.

Own end-to-end payroll and benefits operations across multiple entities, ensuring compliance, data integrity, reconciliations, and audit readiness. Design controls and scalable automated processes, document workflows, and partner with Finance, People, and Legal to align compensation, benefits, and equity accounting during monthly and quarterly closes.

Owns post-sale relationships for enterprise customers, leading onboarding, driving adoption and renewals, coordinating cross-functional teams, identifying risk, and translating customer feedback into product and commercial outcomes.

Lead and manage a large software engineering team building a cloud-based platform. Provide technical coaching, oversee Agile delivery, participate in architecture, ensure project schedules, promote best practices, assess risks, and drive scalable solutions while collaborating cross-functionally and fostering continuous improvement.

Take ownership of end-to-end product and marketing design across web, native apps, print, and patient-facing materials. Build and maintain a scalable Figma design system, partner with product and engineering from problem definition through launch, ensure implementation quality, and iterate using data and customer feedback to drive measurable outcomes.

Build, run, and improve AI-driven automations for FP&A, tax, and finance operations. Connect ERP, spend, equity, HRIS, and CRM systems to LLM-powered agents, maintain auditable workflows, and expand the finance team's AI capabilities while supporting forecasting, budgeting, reporting, and month-end close.