Director of Payroll Tax Training

OSV

81d

About The Position

The Director of Tax Training will provide strategic leadership for OneSource Virtual's comprehensive customer training organization, overseeing the development and delivery of world-class training programs for the tax compliance platform. This executive role requires a visionary leader who can build and execute communication plans, handle critical conversations with staff and clients, and drive innovation in training methodologies. The Director will clearly identify and mentor successors, prepare materials for executive presentations, develop measurable goals aligned with company objectives, and effectively negotiate training delivery with multiple stakeholder groups. This position combines deep expertise in instructional design and adult learning with executive leadership capabilities to ensure customers achieve maximum value from the tax compliance platform through exceptional training experiences.

Requirements

• Bachelor's degree in Education, Instructional Design, Business Administration, or related field; Master's degree strongly preferred.
• 8+ years of training and development experience with demonstrated progression through increasing levels of responsibility and strategic impact.
• 6+ years of leadership experience managing training organizations, with responsibility for strategic planning, team development, and organizational design.
• 5+ years of experience in customer-facing training roles, preferably in SaaS, technology, or financial services environments.
• Proven track record of building training organizations from concept to implementation with measurable business impact and customer success outcomes.
• Executive presentation and communication experience with ability to represent the organization at industry events and deliver strategic information to senior leadership.
• Advanced experience with AI and educational technology including strategic implementation of learning management systems and innovative training platforms.
• Understanding of payroll tax compliance sufficient to guide training strategy and ensure alignment with regulatory requirements.

Nice To Haves

• Advanced certifications in training and development (CPTD, CPLP, Ph.D. in Education) demonstrating commitment to professional excellence.
• Experience in enterprise software or financial services training with understanding of complex regulatory environments and compliance requirements.
• Thought leadership experience including publications, speaking engagements, and industry association leadership in training and development fields.
• International training experience with ability to design programs for global audiences and multi-cultural learning environments.
• Advanced AI and machine learning expertise for educational applications including personalized learning systems and automated content generation platforms.
• Budget management and P&L responsibility for training organizations with understanding of training ROI measurement and optimization.
• Merger and acquisition experience with integration of training programs and organizational culture alignment during periods of change.
• Partnership development experience with educational institutions, certification bodies, and industry training organizations.
• Digital transformation experience leading organizations through technology adoption and process modernization initiatives.
• Executive coaching and leadership development expertise with track record of developing next-generation training leaders and organizational capabilities.

Responsibilities

• Build and execute comprehensive communication plans for training initiatives across customer success, product development, sales, and executive teams to ensure alignment and optimal training outcomes.
• Handle critical conversations with staff, peers, and clients regarding training effectiveness, customer satisfaction issues, and complex implementation challenges.
• Clearly identify and actively mentor successors within the training organization, developing leadership capabilities and ensuring knowledge transfer continuity.
• Prepare basic materials for new business presentations and deliver training-focused content to support sales efforts and customer acquisition initiatives.
• Prepare and deliver information for business and technology audits related to training programs, customer satisfaction metrics, and educational compliance standards.
• Develop measurable goals for the training organization that align with company objectives and drive customer success, platform adoption, and revenue growth.
• Effectively negotiate and coordinate delivery with customer success, product development, and sales teams to ensure training programs support broader organizational initiatives.
• Take decisive action to achieve group and individual goals, making strategic decisions that optimize training effectiveness and customer outcomes.
• Support accountability for training work fully or partially produced by the team, ensuring quality standards and customer satisfaction metrics are consistently met.
• Lead strategic development of training curriculum, methodologies, and delivery platforms to ensure customers receive world-class educational experiences that maximize platform value and compliance success.
• Drive AI integration strategy for training operations, implementing advanced technologies for personalized learning, automated content creation, and intelligent assessment systems.
• Establish and maintain strategic partnerships with industry training organizations, certification bodies, and educational technology providers to enhance training capabilities.
• Oversee development of certification programs and competency frameworks that create clear value propositions for customers and differentiate OneSource Virtual's training offerings.
• Lead cross-functional collaboration with product development teams to ensure training considerations are integrated into platform design and new feature development.
• Establish training metrics and KPIs that demonstrate business impact, customer satisfaction, and ROI on training investments while driving continuous improvement.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: Master's degree
• Number of Employees: 501-1,000 employees