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.
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.
- 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.
- 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.
- 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.
Skills Required
- J.D. from an ABA-accredited law school
- Minimum 10 years of relevant commercial or corporate legal experience
- Substantial experience supporting BPaaS and SaaS businesses
- Experience leading complex, high-value enterprise technology transactions, including SaaS and BPaaS licensing agreements
- Significant experience with data protection, privacy, and AI-related laws, including GDPR, CCPA, and EU AI Act
- Experience with information security contract terms
- Outstanding drafting, negotiation, communication, and interpersonal skills
- Ability to independently manage complex, business-critical matters and competing priorities
- Exceptional legal and business judgment in a fast-paced, high-growth environment
- Ability to improve legal processes and develop scalable contracting resources
- Active bar license in state of residence
OneSource Virtual Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about OneSource Virtual and has not been reviewed or approved by OneSource Virtual.
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Healthcare Strength — Healthcare coverage is presented as comprehensive, including medical, dental, vision, life/disability, and mental-health support, with both copay and HDHP/HSA-style options. Domestic-partner eligibility and standard support services like an EAP are also described as available.
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Leave & Time Off Breadth — Time-off and flexibility are portrayed as comparatively strong, with PTO/“unlimited” or flexible time-off framing and paid volunteer time referenced. Remote work is repeatedly positioned as a valued part of the overall rewards experience tied to work–life balance.
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Wellbeing & Lifestyle Benefits — Financial-wellbeing and lifestyle add-ons are highlighted through earned-wage access and wallet-style tools (e.g., myFlexPay/myFlexWallet) alongside mentions of items like a fitness stipend and company-sponsored events. These extras are framed as modern perks that can improve day-to-day benefits usefulness beyond core insurance.
OneSource Virtual Insights
What We Do
OneSource Virtual (OSV) is the Workday partner that has helped more than 1,300 companies with everything from deployment to maintenance to payroll and more—all to make the day more doable. Founded in 2008, OSV pioneered Business Process as a Service (BPaaS) and has become the leading provider of automated solutions for organizations of all sizes using Workday, delivering services with unparalleled choices, unwavering commitment, and uncompromising care.
