Senior HR Operations Leader Role at AI Startup Leena

Senior HR Operations Leader Role at AI Startup Leena — Remote This is a senior individual contributor / practice leader role at a well-funded AI startup (Leena AI has raised over $30M), reporting directly to a co-founder — a strong green flag for visibility, speed of impact, and equity upside. The role sits at a genuinely rare intersection of deep HR domain expertise and AI product development. Compensation context: No salary is listed, but roles of this seniority (12+ years, enterprise HR leadership, techno-functional, pre-sales credibility) in US enterprise AI/SaaS typically range from $180K–$250K+ OTE in total compensation, with meaningful equity at this stage of company growth. Candidates should negotiate aggressively given the breadth of responsibilities. AI agent design and product ownership — a highly marketable, forward-looking skill set Enterprise SaaS go-to-market (pre-sales, RFPs, analyst relations) without a quota Cross-functional influence at the C-suite level (CHROs, CPOs) Green flags: Broad ownership, founder proximity, no sales quota, ability to grow a team, and your domain expertise literally becoming the product. Watch-outs: The role spans build, delivery, and sales support — that's a wide remit for one person at 50/25/25. Early-stage prioritization pressure is real. Candidates should probe how the team will scale to support these three tracks. The absence of listed benefits is also worth clarifying during interviews. About Leena AI Leena AI is an enterprise agentic AI platform for HR, IT, and Finance. Our AI Colleagues don't just answer employee questions — they run the work behind them: case handling, approvals, and transactions across systems like Workday, SAP SuccessFactors, and ServiceNow. We've built the platform. Now we're going deeper into the HR operations problems that cost enterprises the most — payroll issues, time card exceptions, benefits enrollment and life events, and job and compensation changes. These are the transactions where errors cost real money, employees feel the impact directly, and HR operations teams lose hours fixing them. Building agents for them takes someone who has lived those problems. The Role We're hiring a techno-functional HR leader who has run HR operations at scale — payroll, time, benefits and employee changes — and wants to turn that experience into AI Colleagues that solve real HR operations problems, not just answer questions. You'll report directly to a co-founder of Leena AI. You'll wear three hats, in this order of priority: Build — own the domain for our high-value HR operations agents. Make sure they get transactions right, follow each customer's policies, and hand off to humans at the right moments. Deliver — join customer implementations when an agent needs to be tailored to a customer's policies, pay and time rules, or system setup. Represent — join pre-sales conversations with CHROs, payroll and HR operations leaders, so buyers see that Leena AI brings industry expertise, not only technology. There is no sales quota. What You’ll Do Build high-value HR agents (approx. 50% of your time) Own the domain for agents that handle high-stakes HR operations work: payroll issues, time card exceptions, benefits enrollment and life events, and job and compensation changes. Follow the chain across systems. A promotion, transfer, or status change has to land correctly in pay, time rules, and benefits eligibility. The agents you build won't replace the system of record — they'll make sure each change lands right everywhere, and catch it when it doesn't. Design how agents catch problems early — missing punches, unapproved timecards, late pay-rate changes, benefit deduction mismatches, eligibility gaps — and who they chase to fix each one before it reaches an employee. Design how agents resolve issues end to end — "my pay is wrong", "my benefits didn't start", "my promotion isn't showing": investigate across systems, find the root cause, route the fix for approval, and explain the outcome to the employee. Define the edge cases engineers won't know exist: retro pay, overtime and shift rules, multi-state taxes, mid-year life events, retroactive job changes, mid-period terminations. Find where issues and cost concentrate at each customer — volume, rework hours, cost per error — and build the business case for each agent. Build realistic test scenarios and review agent behavior for domain correctness before it reaches customers. Co‑owner the roadmap with Product. Measure what buyers care about: errors caught before they reach employees, rework hours saved, time to resolve an employee issue. Tailor agents for customers (approx. 25% of your time) Join implementation calls when a customer's HR policies or processes need the agent designed around them. Translate a customer's HR policies, pay rules, union agreements, and system setup into agent behavior the delivery team can configure. Advise customer HR leaders on process redesign, rollout, and change management. Step in on escalations where the question is "is the agent doing the HR process right?" Bring field learnings back into the product so the next customer gets them by default. Represent Leena AI in the market (approx. 25% of your time) Join discovery and demo calls with CHROs, payroll, HR operations and HRIS leaders, and speak their language. Run process deep-dive workshops with prospects and build the ROI case for each agent. Own the functional HR answers in RFPs. Be an external voice: webinars, customer advisory boards, analyst briefings, and content on where AI changes HR operations. Requirements What you bring: 12+ years in HR, including 5+ years leading HR operations, HR shared services, or payroll in a large enterprise (5,000+ employees), or leading HR operations and payroll transformations for such enterprises at a consulting firm, payroll provider, or HCM implementation partner. Hands‑on ownership of high-volume HR transactions — payroll accuracy, time and attendance, benefits enrollment and life events, job and compensation changes. You know where they break and what that costs. Systems know-how across the HR stack: how HR, time, benefits, and payroll systems feed each other, and where data breaks between them. Functional depth in platforms such as Workday, SAP SuccessFactors, Oracle HCM, UKG, or ADP. You've led at least one HR technology implementation or HR transformation from design through go‑live. Techno-functional comfort: you can read a process flow or an API spec at a conceptual level, write structured requirements, and test whether a system does what it should. No coding required. Business sense: you can size a process by volume, rework hours, and error cost, and make the case for automating it. Working knowledge of US HR compliance — FLSA and overtime, multi‑state wage, hour and tax rules, FMLA, ACA, and ERISA. Executive presence with CHRO‑level audiences: you can run a workshop, present a vision, and handle skeptical questions. Curiosity about AI — you've used generative AI tools and have a view on where they help and where they don't. Nice to have: Experience with organizations running several HR, time, benefits, and payroll vendors side by side. Global HR operations or payroll experience across multiple countries. Time at a payroll provider, benefits administrator, HCM implementation partner, or an HR transformation practice at a consulting firm. Hands‑on with HR automation: ServiceNow HR Service Delivery, Workday Extend or Studio, RPA, or workflow tools. Certifications such as CPP (Certified Payroll Professional), CEBS, SHRM‑SCP, or Workday Pro. Exposure to where HR meets IT and Finance — access changes on job moves, payroll‑to‑general‑ledger posting. Why This Role Build a new practice. You'll define how Leena AI's HR agents handle payroll, time, benefits, and job changes, and grow a team as the practice scales. Your experience becomes the product. The edge cases you've fixed by hand become the rules our agents follow at enterprise customers. Work across the whole company. Product, Engineering, customers, and Sales all rely on your judgment, and you report directly to a co‑founder. Is this role fully remote or office-based? The job posting does not specify an office location, and the location hint indicates the United States broadly. Given the customer‑facing and implementation responsibilities, candidates should confirm remote work expectations during the interview process. Is there a sales quota attached to the pre‑sales responsibilities? No — the posting explicitly states "there is no sales quota." The pre‑sales involvement is about bringing HR domain credibility to buyer conversations, not closing deals. What HR systems experience is required for this role? Functional depth in platforms such as Workday, SAP SuccessFactors, Oracle HCM, UKG, or ADP is required. You need to understand their processes, data, and integrations, though hands‑on configuration is not necessary. Does this role require coding or technical development skills? No coding is required. The role calls for "techno‑functional comfort" — the ability to read process flows or API specs conceptually, write structured requirements, and test system behavior. What is the seniority level and reporting structure for this role? This is a senior leadership role requiring 12+ years of HR experience, including 5+ years in HR operations leadership at large enterprises. You will report directly to a co‑founder of Leena AI. Remote work & career advice that actually works. #J-18808-Ljbffr Leena AI