Sr. Director - Product Operations

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. 

The Sr. Director of Product Operations is responsible for designing, scaling, and continuously improving the company's Product Operating Model. This executive serves as a force multiplier for Product leadership, ensuring teams have the clarity, systems, insights, governance, and capabilities required to deliver measurable outcomes. Partnering closely with Product Management, Engineering, Design, Customer Success, Marketing, Sales, Operations, and Executive Leadership, this leader creates the environment in which empowered product teams can thrive. The role focuses on organizational effectiveness, portfolio visibility, decision quality, commercialization readiness, and execution excellence rather than direct ownership of product strategy or roadmap decisions.

Key Responsibilities

Product Operating Model Leadership

• Define and evolve the company's Product Operating Model.
• Establish consistent practices for strategy, discovery, planning, delivery, measurement, and portfolio management.
• Create clarity around decision rights, accountability, operating rhythms, and governance.

Strategy Execution and Portfolio Management

• Connect company strategy to product investments, priorities, and outcomes.
• Lead annual and quarterly planning processes and drive outcome-based planning through OKRs.
• Provide visibility into portfolio performance, investment allocation, risks, and dependencies.

Product Commercialization and Market Readiness

• Establish and lead the company's commercialization framework from launch through adoption.
• Ensure cross-functional readiness across Product, Sales, Marketing, Customer Success, and Operations.
• Drive consistent launch planning, stakeholder reviews, training, and customer communications.
• Measure adoption, business impact, and post-launch success to continuously improve outcomes.

Customer Insight and Product Discovery

• Build organizational capabilities for continuous discovery and evidence-based decision making.
• Establish repeatable practices for customer research, feedback collection, and market learning.
• Ensure product teams incorporate customer insights into strategic and tactical decisions.

Product Metrics and Business Insights

• Define product health, adoption, engagement, retention, and business impact metrics.
• Develop executive dashboards and reporting frameworks that enable informed decision making.
• Promote a culture focused on outcomes over outputs.

Product Team Enablement and Operations

• Develop onboarding, training, playbooks, standards, and best practices that increase team effectiveness.
• Optimize product tooling, workflows, and operating rhythms.
• Leverage AI, automation, and emerging technologies to improve organizational productivity.

Cross-Functional Leadership

• Foster alignment across Product, Engineering, Design, Sales, Marketing, Customer Success, and Operations.
• Improve transparency, communication, and organizational effectiveness.
• Eliminate friction that slows decision making, customer value delivery, and business outcomes.

Qualifications and Success Measures

Qualifications

• 10+ years of progressive leadership experience in Product Management, Product Operations, or Product Strategy.
• Proven success building and scaling high-performing product organizations.
• Deep knowledge of modern product operating models, product management practices, and outcome-based planning.
• Strong analytical, organizational, and executive communication skills.
• Demonstrated ability to lead through influence and drive organizational transformation.
• Experience implementing product metrics, portfolio management, governance, and planning frameworks.
• Passion for customer-centric product development and continuous improvement.

Success Measures

• Increased effectiveness of product teams.
• Improved product delivery predictability and execution quality.
• Strong adoption of customer discovery and insight-driven decisions.
• Achievement of product and business outcomes through OKRs.
• Enhanced portfolio visibility and investment decision quality.
• Faster and higher-quality decision making.
• Commercialization readiness, launch execution quality, and post-launch adoption.
• Strong cross-functional alignment and collaboration.

#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.