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 drafting/review assistants) to increase efficiency across a high-volume contract pipeline.

Qualifications

• J.D. from an ABA-accredited law school.
• Minimum of 10 years of relevant commercial/corporate legal experience, including substantial experience supporting BPaaS and SaaS businesses.
• Outstanding drafting, negotiation, communication, and interpersonal skills, with a proven ability to build trusted advisor relationships across the organization.
• Proven ability to independently manage numerous complex, business-critical matters and competing priorities.
• Demonstrated experience leading complex, high-value enterprise technology transactions, including SaaS and BPaaS licensing agreements with Fortune 500 and other sophisticated enterprise customers.
• Significant experience with data protection, privacy, and AI-related laws (e.g., GDPR, CCPA, EU AI Act) and information security contract terms.
• Exceptional judgment with the ability to balance legal risk and business objectives in a fast-paced, high-growth environment.
• Demonstrated ability to improve legal processes, develop scalable contracting resources, and drive operational excellence.

Licensing Requirements

• Must have an active bar license in state of residence.

#LI-REMOTE

You are encouraged to learn and share ideas when you join the OneSource Virtual team. We reward innovative thinking, fresh perspectives, creative collaboration, and hard work. As an organization experiencing routine strategic growth, we are always on the lookout for intelligent, talented, and forward-thinking professionals to join our team. OSV employees enjoy a values-based culture, upward mobility, and professional development with opportunities of all kinds.