VP, Technology 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. 

Position Summary/Objective

The VP of Technology Operations is responsible for promoting operational discipline, structured planning, and accountability. This role reports directly to the CTO and operates cross-functionally across Engineering, Product, QA, and R&D to ensure continuity of process and performance.

Essential Functions/Duties/Responsibilities

• Define and own the organizational standard for technology planning.
• Work with Product Management and Operations leadership to ensure every platform delivers on the development plan with measurable outcomes in production.
• Maintain a consolidated cross-platform view of plans and delivery status for CTO review.

• Serve as the permanent owner of IT operational processes through their complete maturity lifecycle.
• Continuously assess the maturity of owned processes and drive continuous improvement.
• Proactively identify emerging operational gaps and work with the appropriate resources to develop strategies for addressing them.
• Act as an early warning system for the CTO: surface operational drift, quality degradation, and process gaps before they require executive mandates to correct.

• Own the end-to-end incident management lifecycle across departments and departmental groups including process definition, role execution, stakeholder communication, and post-incident review.
• Ensure Triage and Communication Lead roles are assigned and performed on every qualifying incident. Train and develop the people filling these roles so they can execute with confidence, not just compliance.
• Build and maintain stakeholder communication templates and distribution standards — who receives what communication, in what format, at what point in the incident lifecycle, for each severity level.
• Own the customer impact matching process during incidents, including driving access to and maintenance of customer service and operational contact lists in partnership with Operations, Sales, and Account Management.

Qualifications and Experience

• 10+ years of technology leadership experience, with at least 5 years in a senior role within a high-volume enterprise environment — financial services, payments, payroll, or comparable regulated industry strongly preferred.
• Demonstrated experience owning and maturing operational processes across incident management, RCA, and technology planning in organizations of 75+ engineering staff.
• Experience driving quality culture changes in engineering organizations — not as a QA practitioner, but as a leader who makes quality outcomes visible, consequential, and structurally unavoidable.
• Proven ability to influence peers at the VP level without direct authority, and to escalate constructively when collaboration stalls.
• Experience building communication frameworks and stakeholder notification standards for production incidents in regulated or customer-facing environments.
• Track record of building planning cadences that persist and evolve after initial rollout.
• Strong communication skills. This role produces frameworks, templates, and reports that must be clear to audiences ranging from support staff to executive leadership.

Preferred Qualifications

• Fintech, payroll, or payments domain experience. Understanding of the regulatory and penalty environment around tax and payroll processing is a meaningful advantage.
• Experience managing or closely partnering with Tier 1 / Tier 2 support organizations in a production software environment.
• Familiarity with high scale and high growth rate platforms and enterprise IT maturity efforts.
• Experience building trust with long-tenured, deeply knowledgeable staff during organizational transitions.
• Exposure to distributed engineering teams across inside and outside of the US

Other Duties

Please note that this job description is not intended to provide a complete list of all activities, duties, or responsibilities required of the employee for this position. Duties, responsibilities, and activities may change at any time with or without notice.

#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.