Engineering Manager, AI Conversation Platform

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.

Location: Toronto, Canada with 1 day a week in office Note: travel to Quebec required up to 20% of time  Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. Toast is driven by building a platform that helps our customers adapt, take control, and get back to what they do best: building the businesses they love. International expansion is a critical growth engine for Toast's future. Outside the US, we currently operate in Canada, UK, Ireland, and Australia and are actively growing our product platform in these markets. We are seeking a Senior Product Manager to own the Canadian product roadmap including depth & differentiation in our current customer base and expansion into new regions like Quebec. You will work closely with engineering, design, sales, finance, operations, and marketing partners to deliver a product that helps our customers thrive. In this unique and highly visible role, you will be the primary advocate for the Canadian restaurant ecosystem and have a direct impact on how Toast serves customers in Canada. A day in the life (Responsibilities)  * Define, prioritize, and deliver strategic roadmap initiatives that improve the value proposition of Toast for our customer base * Champion field research & validation: Spend time with customers in Canada to understand how the existing product must evolve to meet their unique customer needs and operational requirements. * Plan and execute discovery, rapid prototyping, and in-restaurant pilots; iterate based on operational feedback and scale successful experiments. * Collaborate with localization and international teams to lead our launch into Quebec  * Define pricing, packaging, and go-to-market strategy with Product Marketing, Sales, and Operations; identify commercial models that fit restaurants of different sizes. What you'll need to thrive (Requirements) * ~6+ years shipping complex software or payments products with demonstrated ownership of multi-team programs or a major product portfolio * Proven track record taking a product from discovery through prototype and pilot to scale. * Experience conducting on-site discovery and validating prototypes in operational environments (restaurant or other physical venues). * Exemplary stakeholder management and ability to align senior partners across sales,, engineering, ops, and GTM, especially on high-visibility initiatives. * Communication & influence. Clear, persuasive written and verbal communication; able to synthesize technical tradeoffs and business value for executives and partners. * Experience launching or running Quebec programs, including French language skills 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. 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 $140,000—$190,000 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.