Top Tech Jobs & Startup Jobs in Chicago, IL

Leads insightsoftware’s global disputes and litigation function, overseeing commercial, IP, contract, regulatory, vendor, and employment matters across 40+ countries. Manages litigation strategy, outside counsel, budgets, settlements, discovery, legal holds, risk processes, and reporting. Serves as principal employment law advisor to HR and business leaders on workforce issues, compliance, policies, investigations, and cross-border matters. Directly manages and develops a legal team while advising senior leadership.

Leads the strategy, governance, operations, and continuous improvement of a global, multi-brand web ecosystem. Oversees web development, UX/UI, CMS operations, publishing, infrastructure, agencies, and multidisciplinary teams. Develops technical roadmaps, operating models, governance frameworks, and scalable delivery processes while partnering with SEO, analytics, marketing, IT, and product teams. Directs migrations, platform consolidations, rebrands, and digital transformation initiatives, ensuring accessible, secure, high-performing websites that support engagement, conversion, and business growth.

Own the AI Services product strategy, roadmap, and execution for agentic workflows, MCP tools, connectors, and AI quality infrastructure. Define agent behavior, evaluation frameworks, integrations, metrics, and risk controls while partnering closely with engineering, architecture, security, legal, and consuming product teams. Drive adoption across the portfolio, make technical trade-offs, communicate outcomes to leadership, and deliver reliable AI capabilities for enterprise finance and accounting users.

Leads global engineering teams and multiple EPM product lines through legacy modernization, SaaS and multi-tenant development, AI-enabled software delivery, customer-facing AI feature development, and operational excellence. Owns engineering strategy, quality, reliability, DORA outcomes, security, budgets, vendors, staffing, and organizational transformation while delivering reliable finance applications and cloud migrations.

Serves as the equity compensation subject matter expert for product and engineering teams. Translates equity plan rules, tax requirements, ASC 718 standards, and reporting needs into functional specifications, workflows, acceptance criteria, and test cases. Partners in Agile planning, validates technical designs, advises on data structures and integrations, monitors regulatory changes, and trains cross-functional teams on equity concepts and compliance.

Own financial and administrative equity reconciliations during customer migrations to the NextGen platform. Reconcile ASC 718 expense, tax, disclosures, diluted EPS, participant data, grants, and transaction histories. Analyze discrepancies, perform root-cause analysis, create comparison reports and audit documentation, and coordinate resolutions across data, product, and reconciliation teams. Serve as a senior customer contact, manage deliverables and SLAs, lead customer conversations, and mentor junior contributors.

Provides technical support to corporate and broker clients by analyzing data, managing file feeds, auditing relational databases, writing reports, and troubleshooting interfaces. Tests and escalates product defects and data issues to engineering and product teams, supports sprint prioritization, manages Salesforce cases, responds to customer inquiries, and documents knowledgebase solutions. Requires SQL, FTP, data management, advanced Excel, strong communication, and problem-solving skills; finance, equity compensation, and ASC 718 knowledge are preferred.

Leads commercial and revenue operations for a high-volume B2B SaaS sales model. Consolidates pipeline and forecasts, analyzes bookings and sales metrics, identifies at-risk deals, removes cross-functional blockers, drives sales play adoption, and provides leadership with accurate, real-time execution visibility across regions and channels.

Leads retention operations for a high-volume B2B SaaS customer base, tracking GRR, NRR, churn, cohort health, expansion opportunities, and performance forecasts. Consolidates customer health signals, identifies at-risk cohorts, conducts root-cause analysis, and partners with customer success, product, and marketing on scalable retention and expansion initiatives. Maintains dashboards, tracks interventions, improves renewal processes, and reports actionable insights to senior leadership.

Serves as a strategic finance advisor, owning P&L analysis, financial modeling, budgeting, forecasting, cash flow analysis, variance reporting, and performance management. Partners with business leaders on pricing, deal structuring, cost optimization, headcount planning, M&A support, and strategic initiatives. Prepares executive and board-ready reporting, maintains financial controls and data integrity, and improves analytical processes using financial platforms and AI tools.