Head of People Technology

About Toast and the Role

Toast is an all-in-one platform designed specifically for restaurants, integrating point-of-sale, payments, marketing, payroll, and more to streamline restaurant operations, boost revenue, and enhance guest experiences. Committed to fostering an inclusive, high-performing work environment, Toast is scaling its People Technology ecosystem to improve experiences for employees, managers, candidates, and People teams.

The Head of People Technology will lead a team dedicated to evolving and expanding Toast's People Technology framework, focusing heavily on Workday along with recruiting technologies and integrations. This role includes managing Workday configuration, administration, security, reporting, and business processes, plus overseeing recruiting technology such as Greenhouse. The position requires building strategic vendor partnerships, reducing technical debt, enhancing self-service capabilities, and using AI and automation responsibly to optimize workflows and efficiency.

Key Responsibilities

• Lead and mentor a high-performing People Technology team responsible for Workday and recruiting tech configuration, administration, reporting, security, and integrations.
• Own Workday strategy including HCM configuration, permissions, security, business processes, governance, and system optimization.
• Manage the roadmap and strategy for Greenhouse and the broader talent acquisition technology stack, ensuring seamless integration and user alignment.
• Collaborate closely with Talent Acquisition Operations to translate recruiting needs into technology strategies, prioritize roadmaps, design systems, and drive adoption.
• Develop a clear, balanced roadmap for Workday and recruiting technology that meets compliance, scalability, and business priorities.
• Reduce technical debt by streamlining processes, improving governance, and simplifying system design.
• Enhance self-service options for employees, managers, candidates, and People teams through scalable workflows, automation, and user-friendly documentation.
• Simplify and strengthen permissions, access governance, security, data integrity, and SOX compliance across all People systems.
• Oversee integrations and data exchanges between Workday, Greenhouse, and related systems to minimize manual effort and increase accuracy.
• Leverage AI, automation, and workflow intelligence to responsibly boost operational efficiency and user experience.
• Partner with cross-functional teams including IT, Security, Legal, Finance, Payroll, and People analytics to align tech decisions with business and risk needs.
• Implement formal processes for intake, prioritization, releases, documentation, and change management in a fast-paced environment.
• Establish and nurture strategic vendor relationships to maximize platform value and innovation adoption.
• Serve as the escalation point for complex system issues, leading root cause analysis and remediation efforts.

Experience and Skills Required

• Over 15 years of experience in HR technology, HRIS, People systems, or related fields.
• Proven leadership with experience coaching and developing high-performing teams.
• Extensive expertise in Workday including HCM configuration, security, permissions, reporting, and governance.
• Track record of managing Workday roadmaps in demanding, complex environments.
• Strong knowledge of HR systems integrations, data flows, access controls, and compliance practices.
• Experience reducing technical debt and simplifying business processes in HR systems.
• Familiarity with compliance requirements including audit and SOX controls within HR platforms.
• Knowledge of recruiting technologies, preferably hands-on with Greenhouse ATS.
• Experience managing strategic vendor relationships for HR and People Technology platforms.
• Ability to evaluate vendor products including AI features, balancing business value, compliance, and user experience.
• Excellent communication and stakeholder engagement skills, capable of translating tech concepts into business impact.
• Strong judgment in prioritizing tasks balancing urgency, risk, and long-term system health.

Preferred Qualifications

• Workday certifications (HCM, Security, Reporting, Recruiting, Compensation).
• Direct administration or roadmap responsibility with Greenhouse.
• Experience driving technology transformations in high-growth or complex environments.
• Expertise in simplifying role-based permissions and audit governance in Workday.
• Working knowledge of Workday integrations, Workday Extend, Prism, and People Analytics tools.
• Background implementing AI and automation to optimize SaaS enterprise platforms.
• Familiarity with additional recruiting tools like GoodTime, BrightHire, assessment platforms, or background checks.
• Experience leading major system configuration, consolidation, or optimization projects.
• Comfort working with distributed or offshore technology teams.

Additional Information

This position prioritizes candidates located near the Boston, MA or Toronto, ON hubs. The role offers an opportunity to influence a pivotal part of Toast's growth and transformation by enhancing People Technology capabilities and experiences.

Toast embraces a hybrid work culture valuing in-person collaboration and individual flexibility. Diversity, equity, and inclusion are core to the company culture, reflecting the diverse restaurant industry they serve.

Toast is committed to accessible and inclusive hiring processes, providing accommodations for candidates with disabilities upon request.

Note on Employment Law: In the U.S., particularly Massachusetts, lie detector tests cannot be mandated as a condition of employment.

Compensation

Salary ranges are subdivided into geographic zones and depend on experience and location:

• Zone A: $186,000 to $298,000 USD
• Zone B: $162,000 to $259,000 USD
• Zone C: $145,000 to $232,000 USD

This compensation includes base pay, potential bonuses, equity, and benefits that support wellbeing and work-life flexibility.

AI at Toast

Toast values continuous learning and employs AI tools throughout the company to accelerate building and customer impact. AI is also used responsibly in the hiring process to assist recruiters and interviewers with administrative tasks without replacing human decision making.