Senior Commercial Counsel

OneSource Virtual (OSV) has worked exclusively with Workday customers since 2008 to deliver compliant, in\-tenant technology and expert services to automate the administrative, transactional tasks of payroll, taxes, earned wage access, accounts payable, and benefits. With over 1,500 customers, 92% retention, and $225\+ billion in treasury movement annually, OSV helps organizations maximize their Workday investment and operate it with confidence. Payroll, benefits, and finance solutions — all in one place. **Position Summary** ==================== OneSource Virtual (OSV) is seeking a Senior Commercial Counsel to join its legal team as a senior, strategic business partner. This role will lead the negotiation and execution of complex, high\-value commercial transactions across OSV’s offerings, partnering closely with Sales, Customer Success, and other business leaders to structure, negotiate, and close complex enterprise agreements. The ideal candidate is a creative, analytical thinker with exceptional legal and business judgment and executive presence. Success in this role is a pragmatic, business\-first legal advisor who is comfortable serving as a trusted partner across the organization while helping the legal team scale and operate more efficiently. **Key Responsibilities** ======================== * Lead strategy, negotiation, and execution of complex, high\-value enterprise agreements, including SaaS, BPaaS, enterprise agreements, data processing agreements (GDPR, CCPA), business associate agreements (DPA, BPA), information security agreements, professional services agreements, and channel/reseller partner agreements. * Draft, review, and negotiate technology and licensing agreements across a high\-volume contract pipeline, including with Fortune 500 and other sophisticated enterprise customers, frequently negotiating on customer paper. * Serve as a strategic legal partner to Sales, Customer Success, and business leadership on deal structuring, risk assessment, and negotiation strategy to accelerate revenue while protecting the business. * Partner cross\-functionally with Finance, Security, Product, and Support to resolve complex commercial and operational issues and support new go\-to\-market models and programs. * Develop, maintain, and continuously improve form agreements, commercial legal templates, and negotiation playbooks to drive consistency and scalability. * Advise on intellectual property licensing, open\-source software usage, and data rights/ownership issues, including AI/ML\-specific considerations such as training data rights, model outputs, algorithmic bias, and ownership of AI\-generated content. * Contribute to workflows and processes that enable the legal team to scale effectively, including contract negotiation, execution, and tracking of contractual obligations. * Create and deliver training to business teams on legal best practices. * Leverage AI\-powered legal tools (e.g., contract analytics platforms, generative AI