Director, Workday Delivery

MedStar Health; United States; Remote; USD 167,000 - 247,000; Full time

Job summary

A leading healthcare organization is looking for a Director of Workday Delivery to join their HR Technology leadership team. This pivotal role will optimize the Workday platform through strategic oversight, innovation, and robust team management. The successful candidate will have a strong background in HR technology with significant Workday experience, guiding the implementation and continuous improvement of the platform for a world-class employee experience.

Benefits

Generous vacation policy

Healthcare benefits

401(k) retirement plan

Qualifications

• 10+ years in HR technology with hands-on Workday expertise.
• Experience managing enterprise-wide tech programs (> $5M).
• Documented success with AI-powered HR capabilities.

Responsibilities

• Lead the execution of HR Technology vision, strategy, and roadmap.
• Manage the Workday release cycle and perform biannual analysis.
• Establish governance and compliance practices for data quality.

Skills

Leadership

Integration management

Agile methodologies

Communication

Stakeholder management

Education

Workday Pro certification

PMP or CSM certification

Tools

Workday

ServiceNow

Job description

Who we are

At Twilio, we're shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions tohundreds of thousands of businessesand empower millions of developers worldwide to craft personalized customer experiences.

Our dedication to remote-first work, and strong culture of connection and global inclusion means that no matter your location, you're part of a vibrant team with diverse experiences making a global impact each day. As we continue to revolutionize how the world interacts, we're acquiring new skills and experiences that make work feel truly rewarding. Your career at Twilio is in your hands.

See yourself at Twilio

Join the team as Twilio's next Director, Workday Delivery

About the job

Twilio is seeking a strategicyethandson Director of Workday Delivery to lead our Workday Services function and serve as a pivotal member of the HR Technology leadership team. This leader will contribute to-and own the execution of-the vision, strategy, and multiyear roadmap for the entire HR technology function, ensuring our platforms are scalable, secure, and intuitive while delivering a worldclass employee experience. Guiding a highperforming Workday team, they will partner with key stakeholder groups (e.g. HR, IT, Security, Compliance, Finance) to fully optimize Twilio's Workday ecosystem for our global organization. We're building tools that make work better for everyone-and we need someone who can enhance our Workday platform with that goal in mind.

Responsibilities

In this role, you'll be responsible for

Strategic Leadership:

• Help shape, contribute to, and execute the HR Technology vision, strategy, and endtoend roadmap.


• Translate longrange vision into quarterly, valuebased delivery plans and OKRs that actually move the needle.


• Sophisticated people leadership capabilities across

Team Management:

• Lead with empathy, clarity, and commitment to helping your team grow.


• Coach and develop highperforming team responsible for Workday configuration, integrations, reporting, and tier3 support.


• Mentor HRIS managers/leads and cultivate a growth mindset across the team.

Delivery & Release Excellence:

• Own the biannual Workday release cycle-impact analysis, regression testing, cutover, and phased enablement of new features.


• Establish endtoend QA frameworks (test plans, UAT playbooks) to ensure performance, security, and data integrity for every change.

Integration Architecture & Ecosystem Management:

• 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.

Innovation & Platform Expansion:

• Champion Workday Extend and other Employee Experience Applications (e.g Eightfold, ServiceNow) to close experience gaps and automate manual work.


• Pilot AIpowered 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.

EndUser Enablement:

• Lead changemanagement, training content, knowledge articles, and workshops to drive sustained user adoption and ROI.Governance, Compliance & Data Quality


• Establish robust changecontrol, security, and datagovernance practices; run scheduled audits and remediation sprints to keep master data pristine and auditready.

Service Operations & Incident Management:

• Define Workday support KPIs (SLA compliance, MTTR), rootcause analysis, and postmortem cadences to reduce repeat incidents.


• Vendor & Budget Management


• Lead the management of the Workday operating budget; negotiate contracts and oversee AMS/implementation partners to hit cost and value targets.

Stakeholder Partnership: Serve as a trusted advisor to HR COEs, HRBPs, IT, Finance, and Security-translating business needs into elegant, techenabled solutions. We want someone who will be the kind of partner our stakeholders look forward to working with - pragmatic, curious, and solution-oriented.

Qualifications

Twilio values diverse experiences from all kinds of industries, and we encourage everyone who meets the required qualifications to apply. If your career is just starting or hasn't followed a traditional path, don't let that stop you from considering Twilio. We are always looking for people who will bring something new to the table!

*Required:

• 10+ years of progressive HRtechnology experience with handson Workday expertise across Core HCM, Benefits, Payroll, Talent, Recruiting, Studio integrations, and reporting.


• Demonstrated success architecting and supporting integrations between Workday and largeenterprise platforms such as ServiceNow, Cornerstone, and Eightfold.


• Proven track record managing enterprisewide technology programs (>$5 M portfolios) using Agile/SAFe delivery methods.


• Leadership of Workday release management and testautomation pipelines.


• Documented success introducing AIpowered HR capabilities (chatbots, predictive insights, RPA) in a regulated environment.


• Proven vendorcontract negotiation skills and ownership of HRIS budgets.


• Workday Pro certification(s) and/or formal Agile credentials (PMP, CSM, SAFe SPC).


• Exceptional communication, stakeholderinfluence, and changeleadership skills.


• Experience operating in a fastpaced, global technology environment.

Desired:

• 3+ years leading managers or technical leads.

Location:

This role will be remote and based in the US

Travel

We prioritize connection and opportunities to build relationships with our customers and each other. For this role, approximately 10% travel is anticipated to help you connect in-person in a meaningful way.

What We Offer

Working at Twilio offers many benefits, including competitive pay, generous time off, ample parental and wellness leave, healthcare, a retirement savings program, and much more. Offerings vary by location.

Compensation

*Please note this role is open to candidates outside of California, Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, New Jersey, New York, Vermont, Washington D.C., and Washington State. The information below is provided for candidates hired in those locations only.

The estimated pay ranges for this role are as follows:

• Based in Colorado, Hawaii, Illinois, Maryland, Massachusetts, Minnesota, Vermont or Washington D.C. : $167,800 - $209,700.


• Based in New York, New Jersey, Washington State, or California (outside of the San Francisco Bay area): $177,700 - $222,100.


• Based in the San Francisco Bay area, California: $197,400 - $246,700


• This role may be eligible to participate in Twilio's equity plan and corporate bonus plan. All roles are generally eligible for the following benefits: health care insurance, 401(k) retirement account, paid sick time, paid personal time off, paid parental leave.

The successful candidate's starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.

Applications for this role are intended to be accepted until July 7, but may change based on business needs.

Twilio thinks big. Do you?

We like to solve problems, take initiative, pitch in when needed, and are always up for trying new things. That's why we seek out colleagues who embody our values - something we call Twilio Magic. Additionally, we empower employees to build positive change in their communities by supporting their volunteering and donation efforts.

So, if you're ready to unleash your full potential, do your best work, and be the best version of yourself, apply now! If this role isn't what you're looking for, please consider other open positions.

Twilio is proud to be an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law. Qualified applicants with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act. Additionally, Twilio participates in the E-Verify program in certain locations, as required by law.