Top Tech Jobs & Startup Jobs in Chicago, IL

Designs and facilitates interactive sales training, onboarding, certifications, coaching, and ongoing seller development. Creates instructor-led and digital learning content, identifies skill gaps, supports AI and sales technology adoption, and partners with sales leaders and subject matter experts. Evaluates training effectiveness and manages enablement initiatives from development through delivery.

Own the post-sale lifecycle for approximately 60 mid-market OnitX customers. Serve as a trusted advisor, monitor account health, conduct business reviews, support renewals, identify expansion opportunities, and collaborate with Implementation, Support, Product, Marketing, and Account Management. The role requires managing complex stakeholder environments, improving customer outcomes, and sharing best practices across the Customer Success organization.

Manage a portfolio of SMB customers by driving adoption, engagement, retention, and growth. Monitor customer health and usage trends, identify risks and opportunities, and provide proactive guidance. Build relationships with Legal Ops, Finance, and IT stakeholders while serving as a trusted advisor. Lead scalable engagement programs, resolve customer challenges, and collaborate with Implementation, Support, Marketing, Product, and Account Management teams.

Manage strategic LegalFiles customer accounts, drive adoption and value realization, guide onboarding and workflow optimization, triage escalations, conduct business reviews, and advocate for product improvements. Partner with legal operations users and technical teams to translate pain points into solutions involving matter management, eBilling, integrations, and automation.

Leads cybersecurity engineering and operations across AWS, SaaS products, corporate infrastructure, Microsoft 365, and AI-enabled applications. Owns security architecture, cloud controls, incident response, vulnerability management, application security, identity protection, automation, and security operations. Manages cybersecurity leaders and technical teams, oversees vendors and testing, and advises engineering, IT, product, compliance, and executives on risk reduction and secure growth.

Assistant Controller will lead monthly, quarterly, and annual close processes; oversee general ledger, accounts payable, payroll, fixed assets, and expense reporting; ensure U.S. GAAP compliance; coordinate audits and tax requirements; improve accounting systems and processes; and supervise accounting staff or outsourced partners. The role supports financial reporting, internal controls, ERP enhancements, and operational scaling in a fast-growing SaaS environment.