Top Tech Jobs & Startup Jobs in Chicago, IL

Prospect for new compliance customers and expand existing accounts through upgrades, cross-sell, and upsell opportunities. Sell Skillsoft’s legal, ethics, safety, and OSHA compliance solutions to complex organizations and senior decision-makers. Manage the full sales cycle, build pipeline through outbound prospecting, negotiate value-based deals, prepare tailored presentations, collaborate cross-functionally, and report on pipeline health and growth objectives.

Provide global employment law counsel to Skillsoft’s People Team and business leaders. Advise on employee relations, workplace investigations, employment agreements, policies, compliance, litigation, disputes, and workforce transitions. Develop scalable legal tools, playbooks, and compliance processes; monitor global legal developments; manage external and local counsel; and support enterprise risk management, ESG, audit, and regulatory compliance programs.

Design and lead end-to-end workforce transformation solutions for enterprise customers. Conduct strategic and technical discovery, advise executives, architect integrated HR and learning technology solutions, build business cases and transformation roadmaps, define implementation and value realization strategies, and oversee delivery alignment. Collaborate with sales, professional services, product, customer success, marketing, and technical teams to improve solution quality, customer outcomes, adoption, and expansion opportunities.

Supports SaaS revenue recognition and royalty accounting under U.S. GAAP and ASC 606. Reviews contracts, prepares revenue schedules and roll-forwards, reconciles billing and general ledger data, manages royalty and reseller reporting, supports audits and SOX controls, and improves accounting processes and systems. Partners cross-functionally to resolve discrepancies and maintain accurate revenue, billing, and ERP data.

Leads North American Market Solutions teams, owning customer experience, ARR growth, retention, expansion, renewals, and platform adoption. Manages and coaches regional leaders, drives solutioning excellence, oversees customer lifecycle execution, and leads organizational transformation. Partners with Sales, Customer Success, Professional Services, Product, Marketing, and Enablement to standardize operating models, improve forecasting and pipeline discipline, develop channel capabilities, and deliver executive-level customer outcomes.

Lead Skillsoft’s analyst relations strategy, building relationships with Gartner, IDC, Forrester, and other industry analysts. Plan briefings and engagement programs, develop messaging and executive materials, coordinate cross-functional stakeholders, manage inquiries and RFPs, monitor analyst coverage and sentiment, and use competitive intelligence to guide product, marketing, and go-to-market strategy. Drive positioning in analyst evaluations, amplify endorsements across marketing and sales channels, and track program KPIs.

Build and operate Skillsoft’s commercial operations function across pricing, deal desk, contract negotiation, RFP support, CPQ, approval workflows, and contract lifecycle systems. The role will redesign end-to-end commercial processes, develop analytics and policies, support implementation and pilots, own exception handling, and drive continuous improvement. It will also lead pricing, discount, conversion, and deal data evaluations while serving as a commercial process owner and subject-matter expert.

Leads the design and operation of an integrated renewals and commercial operations function covering pricing, deal desk, contract negotiation, discount governance, and RFP resources. Redesigns processes using AI and automation, defines CPQ and contract lifecycle requirements, improves ARR and productivity, establishes commercial policies, monitors KPIs, and builds a high-performing team while partnering with Sales, Legal, and Finance.

Administer global equity plans, including RSUs, PSUs, options, vesting, releases, tax withholding, and terminations. Maintain equity data, reconcile Workday integrations, coordinate transfer-agent and payroll activities, and support Forms 3 and 4, Section 16, EDGAR Next, S-8 tracking, proxy calculations, and SOX controls. Partner with Legal, HR, Payroll, Tax, Finance, vendors, and employees while managing international reporting, audits, compliance updates, and process improvements.