Head of People Operations

The Company

Outrider is a software company that is automating distribution yards with electric, self-driving trucks. Our system eliminates manual tasks that are hazardous and repetitive while it improves safety and efficiency. Outrider’s mission is to drive the rapid adoption of sustainable freight transportation. We are a private company founded in 2018 and backed by NEA, 8VC, Koch Disruptive Technologies, NVIDIA, and other top-tier investors. Our customers are Fortune 200 companies and our autonomous trucks are already running in distribution yards. For more information, visit www.outrider.ai

At Outrider, you'll develop, improve upon, and ship cutting-edge software that drives next-generation freight transportation. Your work will directly contribute to autonomous systems that move millions of tons of freight across shipping & logistics centers, revolutionizing the way goods are transported globally. Over time, your contributions will enhance efficiency, safety, precision, and sustainability across the supply chain. Throughout your time at Outrider, you'll collaborate across teams and functions to build and maintain robust systems that keep the global economy moving.

The Role

Outrider looking for a Head of People Operations who can help transition an exciting robotics company from development stage to full commercial scale-up. The ideal candidate will reimagine HR from the ground up using AI, automation, and smart systems -- not as a support function, but as an intelligent, productized, employee-service focused platform. 

Duties and Responsibilities

• Automate everything: Streamline and eliminate manual workflows across recruiting, onboarding, performance, and employee support. Leverage AI agents, no-code automation tools, and off-the-shelf LLMs to collapse the traditional HR stack into lean, intelligent processes.
• Build a self-service people platform: Architect an HR experience that functions like a smart internal product — complete with AI-powered FAQs, dynamic onboarding, and frictionless performance management.
• Use AI as a force multiplier: Design scalable systems that reduce dependency on headcount. Replace repetitive tasks with tools, templates, and agents that grow with the company.
• Operate like a product manager: Work cross-functionally with tech, ops, and finance to launch HR systems that are data-driven, measurable, and aligned to KPIs like time-to-hire, time-to-ramp, engagement feedback, and retention. Measure outcomes with quantifiable metrics and work to improve upon those metrics every month/quarter/year.
• Deliver with an ‘HR-as-a-service’ mindset: Treat People Ops as a core service layer — with internal SLAs, repeatable workflows, and performance dashboards that make the team’s impact transparent and measurable.
• Start clean, build smart: This is a clean-sheet opportunity to reimagine the future of HR with no legacy constraints — an ideal setup for someone who thrives in zero-to-one environments.

Required Qualifications

• AI-native & tool-savvy: You’re comfortable building with modern tools like GPT-4, Notion AI, Zapier, and workflow automation platforms. You’re curious and experimental with how emerging tech can scale team operations.
• People systems expertise: You know your way around platforms like BambooHR, Deel, Rippling, 15Five, Lattice, Ashby, Greenhouse, and other simple/sophisticated HR tools — and you know how to extend their capabilities through integration and automation.
• KPI-driven execution: You think in metrics, OKRs, and dashboards. You run People Ops with the same rigor as product or finance teams.
• Builder mentality: You’re energized by first builds, lean teams, and systems that scale. You prefer creating scalable solutions over adding layers of process.
• Executive presence + operator’s mindset: You can think strategically, execute independently, and communicate clearly across teams — while staying hands-on and iterative.
• Background with sensitive and complex HR matters: you navigate expectations and culture across an employee base that includes on-site, remote, and international; white collar/blue collar; technical and business; and execs/managers/ICs.
• Player/coach with experience managing a team through change: you can be a team of 1 where you’re a productive individual contributor and also enable a team of highly productive players to deliver standout performances, all through rapid change and growth in the function, organization, and company overall.  

Ideal Qualifications

• Experience building or deploying internal tools/AI agents
• A background in product management or systems design
• A track record of driving down cost-per-hire or time-to-hire via automation
• A perspective on what modern HR should look like in an AI-native workplace
• Comfort navigating hybrid work environments and distributed tooling

Compensation & Benefits

• Salary: $135,000 - $160,000
• Equity: Significant equity package commensurate on experience and skills
• Benefits: Full health benefits
• Hybrid (4 days onsite)
• Home office stipend up to $500 to help you create a comfortable and productive workspace.
• Actual compensation is based on several factors, including but not limited to job-related skills, qualifications, experience, and specific work location due to differences in the cost of labor