Manager, People Systems Engineering (Remote Eligible)

Smartsheet

2d•$122,000 - $175,000•Remote

About The Position

Smartsheet's Corporate Systems Engineering team builds and operates software platforms, integrations, and automations that power the company's core business functions. The People Systems Engineering team specifically focuses on the technology platforms that support the entire employee lifecycle, including systems like Workday, Docebo, and Greenhouse. This role is responsible for the technical strategy and long-term architecture of this ecosystem, going beyond individual application management to shape the overall architecture, engineering practices, data strategy, automation, and AI capabilities. The position aims to fundamentally improve employee technology by simplifying processes, reducing manual administration, enhancing employee and manager experiences, and strengthening system architecture through configuration, software engineering, automation, and AI. This role involves leading the engineering team responsible for Smartsheet’s People technology, defining its future technical direction. It requires a strong technical understanding of Workday and the ability to architect a cohesive technology ecosystem that includes various People platforms, integrations, employee data, automation, and AI. The Manager will challenge existing approaches, identify opportunities for simplification and improvement, and define architectural boundaries and data strategies. A key focus will be on evolving towards an API-first, event-driven ecosystem and defining an AI strategy for employee technology. The role also emphasizes introducing modern software engineering practices, improving system observability, and ensuring the technical health of the People Systems portfolio. Collaboration with other engineering teams is crucial to ensure People technology is integrated into the broader enterprise architecture. The Manager will also be responsible for recruiting, mentoring, and developing the engineering team.

Requirements

Bachelor’s degree in Computer Science, Information Systems, Engineering, or a related field — or equivalent practical experience
8+ years of experience across enterprise application engineering, software engineering, HR technology, systems architecture, or related technical disciplines
2+ years of experience managing or formally leading technical teams, with demonstrated ability to develop both people and technical capability
Strong hands-on technical understanding of Workday, including its architecture, data model, security model, business processes, integrations, reporting, and extensibility capabilities
Demonstrated experience defining technical strategy or architecture, rather than solely managing application delivery, configuration, or support
Strong systems thinking and the ability to reason across applications, integrations, APIs, data, identity, automation, infrastructure, and employee experiences as a connected architecture
Experience determining appropriate boundaries between SaaS configuration, platform extensibility, integrations, automation, and custom software development
Experience designing or evolving enterprise data architecture, including systems of record, data models, interfaces, data contracts, quality, governance, and downstream consumption
Experience introducing modern software engineering practices into enterprise SaaS or business systems environments
Experience with testing strategy and automation, CI/CD, observability, release engineering, or other practices that improve the reliability and velocity of enterprise application development
Understanding of modern AI capabilities and the ability to identify practical applications of agents, LLMs, and intelligent automation within enterprise workflows
Experience partnering with Product Managers to combine product strategy, customer needs, and technical strategy into coherent roadmaps and investment decisions
Demonstrated ability to challenge legacy processes and architectures constructively and develop pragmatic modernization strategies rather than simply maintaining the existing environment
Ability to operate across both strategic architecture and detailed technical discussions, including the credibility to challenge engineers, vendors, implementation partners, and business stakeholders
Strong understanding of security, privacy, access control, auditability, and data protection considerations associated with sensitive employee data
Excellent analytical, verbal, and written communication skills, with the ability to communicate complex technical strategies and tradeoffs to technical and non-technical audiences

Nice To Haves

Experience with adjacent People platforms such as Docebo, Greenhouse, or similar technologies is a plus
Experience with Workday Studio, Workday Extend, Workday APIs, cloud platforms, event-driven architectures, AI/agent platforms, or modern automation frameworks is a strong plus

Responsibilities

Own the technical strategy and long-term architecture for the People technology ecosystem, establishing a clear future state across Workday, Docebo, Greenhouse, integrations, employee data, automation, AI, and emerging capabilities
Lead, coach, and develop the engineering team responsible for Smartsheet’s People platforms, creating a culture of technical ownership, experimentation, engineering rigor, and continuous improvement
Serve as a technical leader for Workday, ensuring the platform remains well architected, maintainable, secure, scalable, and appropriately leveraged as a foundational system of record within the broader employee technology architecture
Partner with the Product Manager for People Systems to translate employee and business problems into product and technical strategies, jointly shaping roadmaps while maintaining clear engineering ownership of architecture and implementation
Continually evaluate the People technology landscape and challenge existing assumptions about how employee workflows should operate, identifying opportunities to simplify, consolidate, redesign, automate, or eliminate processes
Define architectural boundaries across People platforms, determining which capabilities should live within Workday or other SaaS applications and where APIs, integrations, custom applications, automation, or AI provide better solutions
Develop the technical strategy for People data, including authoritative sources, data models, system boundaries, data contracts, quality, lineage, access, lifecycle management, and reliable consumption by downstream systems
Drive the evolution of People Systems toward an API-first and event-driven ecosystem where appropriate, reducing unnecessary point-to-point dependencies, manual data movement, and fragile integrations
Define an AI and agentification strategy for employee technology, partnering with AI & Automation Engineering to identify where agents, conversational experiences, intelligent workflows, and AI-assisted processes can meaningfully improve employee and manager experiences
Identify opportunities to move employee interactions away from navigating individual systems and toward simpler, intelligent experiences that orchestrate capabilities across the underlying People technology stack
Establish a deliberate automation strategy across the employee lifecycle, reducing repetitive administration and manual handoffs across recruiting, onboarding, employee changes, compensation, learning, talent, and offboarding
Introduce stronger software engineering practices into the People technology stack, including source control, peer review, CI/CD, environment management, observability, reusable components, documentation, and disciplined release practices where supported by the underlying platforms
Establish a strategy for automated testing across People Systems, progressively reducing dependence on manual regression testing and improving confidence and speed as Workday and connected platforms change
Define engineering standards for Workday configuration and extensibility, including when to use native configuration, Workday Studio, Workday Extend, APIs, integrations, automation, or external services
Improve observability across critical employee workflows, integrations, scheduled processes, and data flows so failures and degradation can be identified proactively rather than through employee or business escalation
Own the technical health of the People Systems portfolio, establishing mechanisms to identify and address architectural debt, fragile integrations, unnecessary customization, obsolete processes, platform limitations, and recurring operational issues
Partner with Integration Engineering, AI & Automation, Data, Identity, Security, and other engineering teams to ensure People technology operates as part of a coherent enterprise architecture rather than as an isolated HR technology stack
Evaluate emerging technologies and platform capabilities, separating meaningful opportunities from technology hype and developing pragmatic paths from experimentation to production
Balance roadmap delivery with architectural modernization, platform reliability, technical debt, security, operational sustainability, and longer-term engineering investments
Establish architecture reviews, technical standards, engineering metrics, and other mechanisms that raise the maturity of People Systems Engineering over time
Communicate technical strategy, architecture decisions, investment needs, risks, and tradeoffs clearly to People & Culture, Product, Engineering, and senior leadership
Recruit, onboard, mentor, and develop engineers with a combination of enterprise platform expertise, software engineering capability, systems thinking, and curiosity about the future of employee technology

Benefits

Employer subsidized medical/vision and dental coverage for full-time employees
401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay)
Monthly stipend to support your work and productivity
Flexible Time Away Program, plus Sick Time Off
US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans
US employees receive 12 paid holidays per year
Up to 24 weeks of Parental Leave
Personal paid Volunteer Day to support our community
Opportunities for professional growth and development including access to Udemy online courses
Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account
Teleworking options from any registered location in the U.S. (role specific)