Director, Workday Delivery

Summary

Join Twilio as the next Director, Workday Delivery, a strategic and hands-on role leading the Workday Services function and serving as a pivotal member of the HR Technology leadership team. Contribute to and execute the vision, strategy, and multi-year roadmap for the entire HR technology function, ensuring platforms are scalable, secure, and intuitive while delivering a world-class employee experience. Guide a high-performing Workday team, partnering with key stakeholders (HR, IT, Security, Compliance, Finance) to optimize Twilio’s Workday ecosystem. Build tools that enhance the Workday platform, focusing on employee experience. Lead change management, training, and knowledge sharing to drive user adoption. Establish robust change-control, security, and data-governance practices. Define Workday support KPIs and manage the Workday operating budget and vendor relationships. Serve as a trusted advisor to stakeholders, translating business needs into tech-enabled solutions.

Requirements

• 10+ years of progressive HR-technology experience with hands-on Workday expertise across Core HCM, Benefits, Payroll, Talent, Recruiting, Studio integrations, and reporting
• Demonstrated success architecting and supporting integrations between Workday and large-enterprise platforms such as ServiceNow, Cornerstone, and Eightfold
• Proven track record managing enterprise-wide technology programs (>$5 M portfolios) using Agile/SAFe delivery methods
• Leadership of Workday release management and test-automation pipelines
• Documented success introducing AI-powered HR capabilities (chatbots, predictive insights, RPA) in a regulated environment
• Proven vendor-contract negotiation skills and ownership of HRIS budgets
• Workday Pro certification(s) and/or formal Agile credentials (PMP, CSM, SAFe SPC)
• Exceptional communication, stakeholder-influence, and change-leadership skills
• Experience operating in a fast-paced, global technology environment

Responsibilities

• Help shape, contribute to, and execute the HR Technology vision, strategy, and end-to-end roadmap
• Translate long-range vision into quarterly, value-based delivery plans and OKRs that actually move the needle
• Lead with empathy, clarity, and commitment to helping your team grow
• Coach and develop high-performing team responsible for Workday configuration, integrations, reporting, and tier-3 support
• Mentor HRIS managers/leads and cultivate a growth mindset across the team
• Own the bi-annual Workday release cycle—impact analysis, regression testing, cut-over, and phased enablement of new features
• Establish end-to-end QA frameworks (test plans, UAT playbooks) to ensure performance, security, and data integrity for every change
• Design and maintain robust, secure integrations that connect Workday with Twilio’s broader HR technology stack (e.g., ServiceNow EC Pro/Now Assist, Cornerstone Learning Hub, Eightfold AI, Qualtrics, Visier) using Workday Studio, EIBs, REST/SOAP APIs, and iPaaS middleware
• Champion Workday Extend and other Employee Experience Applications (e.g Eightfold, ServiceNow) to close experience gaps and automate manual work
• Pilot AI-powered capabilities—while embedding governance for privacy, bias, and accuracy
• You’ll have space to explore new ideas and help define how we use AI, automation, and new tools to drive real employee value
• Lead change-management, training content, knowledge articles, and workshops to drive sustained user adoption and ROI
• Establish robust change-control, security, and data-governance practices; run scheduled audits and remediation sprints to keep master data pristine and audit-ready
• Define Workday support KPIs (SLA compliance, MTTR), root-cause analysis, and post-mortem cadences to reduce repeat incidents
• Lead the management of the Workday operating budget; negotiate contracts and oversee AMS/implementation partners to hit cost and value targets
• Serve as a trusted advisor to HR COEs, HRBPs, IT, Finance, and Security—translating business needs into elegant, tech-enabled solutions

Preferred Qualifications

3+ years leading managers or technical leads

Benefits

• Competitive pay
• Generous time off
• Ample parental and wellness leave
• Healthcare
• A retirement savings program
• Health care insurance
• 401(k) retirement account
• Paid sick time
• Paid personal time off
• Paid parental leave