Director of Engineering, HRIS Core Flows

Rippling•San Francisco, CA

6d•Onsite

About The Position

Rippling HRIS is the system of record for employee and organization data and the control plane for the workflows that change it. We’re looking for an Engineering Director to lead the teams responsible for employee transitions, employee terminations, and a new AI-assisted HR workflow charter. In this role, you will lead a 15-person organization focused on making high-stakes employee lifecycle workflows faster, more reliable, and easier to operate at enterprise scale. You will define the product and technical strategy for AI-assisted workflows that help customers understand employee-change requests, gather missing information, coordinate approvals, and execute approved changes with transparency, human oversight, and auditability. Why this role exists: Manual to agentic: Employee lifecycle workflows should do more of the work. Today, many processes still depend on an admin knowing the right sequence, collecting context, coordinating stakeholders, and following through manually. The opportunity is to make the product an intelligent partner while preserving human judgment, transparency, and control. High-stakes product surface: Transition and termination flows touch some of the most consequential employee changes and have downstream effects across HR, payroll, benefits, IT, and finance. The product must make complex cases feel simple without hiding the underlying controls. Enterprise readiness: Large enterprises bring deeper hierarchies, more policies, fine-grained permissions, global variation, larger bulk operations, and more integrations. The system needs predictable performance, reliability, correctness, and auditability as those dimensions compound. Unified leadership: A combined 15-person team needs one leader accountable for the product strategy, technical direction, org design, talent bar, and cross-functional operating model across the full charter.

Requirements

Experience as an Engineering Director or equivalent leader overseeing a multi-team product engineering organization.
Experience leading through managers and senior technical leaders, with a track record of developing leadership capacity rather than becoming the decision bottleneck.
Experience owning high-stakes, workflow-heavy products or platforms where correctness, permissions, policy, auditability, and integrations matter.
Experience scaling products for complex enterprise customers, including operational edge cases and cross-functional dependencies.
Strong product judgment and technical depth, including the ability to evaluate architecture, sequencing, migration risk, and platform investment trade-offs.
Experience delivering a major product or system transformation while continuing to ship customer-facing improvements.
Experience with AI agents, AI-assisted workflows, decision automation, workflow orchestration, or intelligent enterprise products.
Experience with HR, payroll, benefits, IT, identity, finance, compliance, or other employee-system domains.
Experience with global products that must support country-specific policies, permissions, localization, and audit requirements.
Experience building platforms for bulk operations, asynchronous workflows, observability, and recovery.

Responsibilities

Transform employee lifecycle workflows from manual to agentic: Define the product and technical strategy for an Agentic HRBP that helps customers reason about, prepare, approve, and execute employee changes. Move beyond a conversational front end: connect agents to durable workflow execution, company policy, employee context, permissions, approvals, and observable outcomes. Establish the trust model for high-stakes actions, including clear user intent, human checkpoints where appropriate, explainability, safe failure modes, and complete audit trails. Create a reusable approach that accelerates new agentic use cases instead of producing one-off demos or brittle automations.
Reach enterprise scale: Make Transition & Termination dependable for large, complex companies across organization structures, employment types, countries, policies, and connected systems. Raise the bar for performance, availability, correctness, bulk operations, observability, and recovery across synchronous and asynchronous work. Partner directly with enterprise customers and go-to-market teams to identify the cases that break at scale and translate them into a durable product and platform roadmap. Modernize the underlying architecture while continuing to deliver customer-facing improvements; sequence the work so the transformation creates leverage rather than a prolonged rewrite.
Build a durable organization: Lead and develop a combined 15-person team, including managers, senior ICs, and emerging leaders as the organization evolves. Clarify ownership, decision rights, quality bars, and operating rhythms across the Transition & Termination and Agentic HRBP charters. Hire and retain exceptional talent, raise the leadership bench, and create an environment where product, design, data, AI, and engineering operate as one team. Represent the charter in company-level planning and make clear trade-offs across near-term customer commitments, foundational investments, and long-term bets.