Toast is the all-in-one platform built for restaurants of all sizes. We combine point-of-sale, payments, marketing, payroll, and

more into a single platform that helps restaurants simplify operations, increase revenue, and delight guests. At Toast, we are

committed to creating an inclusive, high-performing culture where every Toaster can do the best work of their career. As we

continue to scale, our People Technology ecosystem plays a critical role in enabling a seamless employee, manager, candidate, and

People team experience.

Toast is looking for a Head of People Technology to lead the team responsible for evolving and scaling our People Technology

ecosystem, with a primary focus on Workday and a connected focus on recruiting technology, integrations, governance, and

experience. You will lead a team responsible for Workday configuration, administration, reporting, security, permissions, business

process design, integrations, and support, while also owning the strategy for Greenhouse and the broader TA technology stack in

close partnership with Talent Acquisition. This leader will build a clear Workday and TA technology roadmap, reduce tech debt,

improve self-service, simplify permissions, strengthen compliance, and create scalable experiences for employees, managers,

candidates, and People teams. You will also identify responsible opportunities to use in-platform AI, automation, and workflow

intelligence to improve efficiency and reduce manual work. A critical part of this role will be building strategic partnerships

with vendors including Workday, Greenhouse, and other People Technology providers to ensure Toast is using its platforms in

best-in-class ways for our size, complexity, and scale.

Note: We are prioritizing candidates located near our hubs in Boston, MA and Toronto, ON.

A day in the life (Responsibilities)

Lead, coach, and develop a high-performing People Technology team responsible for Workday and recruiting technology

configuration, administration, security, integrations, reporting, and support

Serve as the strategic owner of Workday, including HCM configuration, business process design, reporting, permissions,

security, governance, and ongoing optimization

Own the strategy for Greenhouse and the broader TA technology stack, ensuring the ecosystem is scalable, integrated,

well-governed, and aligned to candidate, recruiter, interviewer, and hiring manager needs

Partner closely with Talent Acquisition Operations to translate recruiting process needs into technology strategy, roadmap

priorities, system design, integrations, and adoption plans

Build and manage a clear Workday and TA technology roadmap that balances business priorities, compliance needs, tech debt

reduction, stakeholder demand, team capacity, and scalability

Reduce tech debt by simplifying processes, improving governance, retiring unnecessary complexity, and driving sustainable

system design

Improve employee, manager, candidate, and People team self-service through scalable workflows, automation, documentation,

intuitive experiences, and change management

Simplify and strengthen permissioning, security, access governance, data integrity, SOX readiness, auditability, and controls

across Workday, Greenhouse, and connected systems

Drive integrations and data flows between Workday, Greenhouse, and adjacent People systems to reduce manual work and improve

accuracy

Use in-platform AI, automation, and workflow intelligence to responsibly improve efficiency, decision support, case deflection,

routing, reporting, and user experience

Partner with IT, Security, Legal, Finance, Payroll, TA, People Operations, People Analytics, and People leadership to align

technology decisions with business needs and risk requirements

Establish intake, prioritization, release, documentation, and change management practices that bring transparency and

discipline to a high-demand environment

Build strategic vendor partnerships with Workday, Greenhouse, and other People Technology providers to maximize platform value,

adopt relevant innovation, and influence vendor roadmaps where appropriate

Serve as an escalation point for complex system issues, root cause analysis, and long-term remediation

What you'll need to thrive (Requirements)

12+ years of experience in HR technology, People systems, People operations, HRIS, or a related systems-focused role
3+ years of people management experience, with a track record of coaching, developing, and leading high-performing teams
Deep Workday experience, including HCM configuration, business processes, reporting, security, permissions, and system

governance

Experience building or owning a Workday roadmap in a complex, high-demand environment
Strong understanding of HR systems integrations, data flows, access controls, reporting, and data integrity practices
Experience reducing tech debt, simplifying processes, improving governance, and prioritizing competing stakeholder requests
Experience supporting compliance, audit, SOX, or other control requirements within HR systems
Familiarity with applicant tracking systems and recruiting technology; Greenhouse experience strongly preferred
Experience managing strategic vendor relationships for enterprise HR, Workday, recruiting, or People Technology platforms
Ability to evaluate vendor capabilities, platform releases, AI-enabled features, and best-practice recommendations through the

lens of business value, compliance, scalability, and user experience

Excellent communication and stakeholder management skills, including the ability to translate technical concepts into business

impact

Strong judgment and prioritization skills, with the ability to balance urgency, risk, capacity, and long-term platform health

Nice-to-Have Skills:

Workday certifications in HCM, Security, Reporting, Recruiting, Compensation, or related areas
Direct Greenhouse administration, configuration, integration, or roadmap experience
Experience leading Workday or People Technology transformation efforts in a high-growth technology company or similarly complex

environment

Experience simplifying role-based permissions, security groups, access governance, or audit controls in Workday
Experience with Workday integrations, Workday Extend, Prism, People Analytics, or adjacent reporting tools
Experience implementing AI-enabled features, automation, or workflow intelligence within enterprise SaaS systems
Familiarity with recruiting tools such as GoodTime, BrightHire, sourcing tools, assessment platforms, or background check

providers

Experience leading major configuration, implementation, optimization, platform consolidation, or tech debt reduction

initiatives

Experience working with distributed or offshore support teams

Why Toast?

This is a meaningful opportunity to shape the future of People Technology at Toast during an important phase of growth and

transformation. You will inherit a talented team and a critical platform ecosystem, with the opportunity to bring clarity,

structure, innovation, and scale to how Toast supports employees, managers, candidates, and People teams.

In this role, you will lead a mission-critical function, build a strategic roadmap, reduce tech debt, simplify systems

experiences, strengthen vendor partnerships, and help Toast get the most value from its People Technology investments.

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build

for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from

Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The

people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and

brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a

healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at

https://careers.toasttab.com/toast-benefits.

#LI-HYBRID

The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and

geographic location. In addition to base salary, our total rewards components include cash compensation (overtime,

bonus/commissions if eligible), equity, and benefits.

Pay Range

$150,000—$200,000 CAD

How Toast Uses AI in its Hiring Process

Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with

tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation.

All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring

Our Approach to Hybrid Working

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong

culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations

page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast

Diversity, Equity, and Inclusion is Baked into our Recipe for Success

At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse,

and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our

culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences.

We Thrive Together

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong

culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and

regionally, check out: https://careers.toasttab.com/locations-toast.

Apply today!

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide

reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation

to access the job application or interview process, please contact candidateaccommodations@toasttab.com.

------

For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of

employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Role

Head of People Technology

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Zone A $155,000—$248,000 USD Zone B $135,000—$216,000 USD Zone C $122,000—$195,000 USD How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring Our Approach to Hybrid Working We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast Diversity, Equity, and Inclusion is Baked into our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences. We Thrive Together We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast. Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com. ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.