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Director, Workday Delivery

Remote - Alberta, Canada; Remote - British Columbia, Canada; Remote - Ontario, Canada

Who we are 

At Twilio, we’re shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to hundreds of thousands of businesses and 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 strategic‑yet‑hands‑on 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 multi‑year roadmap for the entire HR technology function, ensuring our platforms are scalable, secure, and intuitive while delivering a world‑class employee experience. Guiding a high‑performing 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 end‑to‑end roadmap.
  • Translate long‑range vision into quarterly, value‑based 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 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.

Delivery & Release Excellence:

  • 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.

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 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.

End‑User Enablement:

  • Lead change‑management, training content, knowledge articles, and workshops to drive sustained user adoption and ROI.Governance, Compliance & Data Quality
  • Establish robust change‑control, security, and data‑governance practices; run scheduled audits and remediation sprints to keep master data pristine and audit‑ready.

Service Operations & Incident Management:

  • Define Workday support KPIs (SLA compliance, MTTR), root‑cause analysis, and post‑mortem 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, tech‑enabled 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 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.

Desired:

  • 3+ years leading managers or technical leads.

Location

This role will be remote, and based in Ontario, Alberta or BC.

Travel 

We prioritize connection and opportunities to build relationships with our customers and each other. For this role, you may be required to travel occasionally to participate in project or team in-person meetings.

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.

The estimated pay ranges for this role are as follows:

  • Based in British Columbia. : CAD 142,800 - CAD 178,500

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

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.

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