Head of People at Numeral

ABOUT NUMERAL - Numeral is transforming how taxes get done. Digital businesses are currently bogged down by a painful web of regulations across 47 states and 50+ countries. We’re eliminating this burden so teams can focus on their core mission. - We’re the largest and fastest growing AI-native tax solution. Started in 2023, Numeral has raised over $57M from Benchmark, Mayfield, Y-Combinator, and many others. We now serve over 2,500 paying customers and have more than tripled our revenue every year in our history. - We’re primarily hiring in our SF and NY offices, but do hire remotely in some cases ABOUT THE ROLE We’re hiring a Founding Head of People to design, build, and lead the People function at Numeral. This is a true 0→1 and 1→N role. You’ll inherit a company that has grown very quickly with extremely strong talent and momentum, but without many of the formal people systems that are required at our current scale: compensation frameworks, performance management, calibration, career paths, manager enablement, and global workforce infrastructure. You will partner closely with the executive team and functional leaders to professionalize how we hire, pay, develop, and retain talent, while preserving the speed, ownership, and high bar that got us here. This role is equal parts strategic architect and hands‑on operator. You will set direction, but you will also personally build the early programs, policies, and muscle memory that define Numeral for years to come. WHAT YOU’LL OWN PEOPLE STRATEGY & LEADERSHIP - Serve as the senior People leader and trusted advisor to the executive team. - Translate company strategy, growth plans, and ARR targets into a clear People roadmap. - Build a scalable People org over time (recruiting, people ops, total rewards, L&D), starting lean and hands‑on. - Establish strong operating cadence around headcount planning, workforce mix (FTE vs contractor), and organizational design. RECRUITING & TALENT SCALING - Own recruiting strategy end‑to‑end across engineering, product, GTM, and operations. - Partner with executives and hiring managers on workforce planning, role design, leveling, and hiring bar. - Build durable recruiting infrastructure: ATS, interviewer training, structured interviews, calibration, and closing discipline. - Develop sourcing strategies and employer branding appropriate for a fast‑growing Series B company. - Ensure hiring quality scales with volume — not at the expense of speed or standards. COMPENSATION, PERFORMANCE & CAREER FRAMEWORKS - Design and implement Numeral’s first formal compensation philosophy and pay bands. - Build performance management from scratch: goal‑setting, reviews, calibration, and feedback loops. - Introduce clear role definitions, leveling, and career paths across functions. - Partner with Finance on budgeting, headcount modeling, equity planning, and compensation tradeoffs. - Ensure fairness, consistency, and defensibility as the company grows. MANAGER ENABLEMENT & CULTURE - Help first‑time and experienced managers scale effectively through rapid growth. - Build core manager expectations around hiring, feedback, performance, and development. - Establish cultural operating principles that reinforce accountability, ownership, and trust. - Support execs and managers through sensitive people situations with sound judgment and discretion. PEOPLE OPERATIONS, POLICIES & COMPLIANCE - Professionalize People Ops for a global workforce (U.S. + international contractors today, with evolving models over time). - Own HR policies, handbooks, and internal documentation. - Partner with Legal and Finance on compliance, risk management, and employee relations. - Improve onboarding, offboarding, and lifecycle experiences so they scale smoothly. - Implement and optimize People systems (HRIS, payroll, benefits, performance tools). WHAT YOU'LL BRING - 7+ years of People leadership experience, with significant time in high‑growth startups. - Prior experience as a first or early Head of People, or a senior People leader who has built functions from scratch. - Deep experience scaling teams rapidly (2–4x headcount) at the Series A–C stage. - Strong command of recruiting, compensation, performance management, and People Ops — not just one area. - Proven ability to partner with executives and influence without bureaucracy. - Comfort operating in ambiguity, with high judgment and bias toward action. - Exceptional communicator: clear, direct, pragmatic, and credible with senior leaders. - Startup mindset: Not scared of ambiguity and hungry for rapid growth - Intensity & Ownership: This is not a 9-5 — we’re scaling rapidly and have a massive opportunity ahead of us. - Customer Obsession: You deeply care about the user experience and solving their problems EVEN BETTER - Experience supporting global teams or mixed FTE/contractor models. - Familiarity with modern People tooling (Ashby, Rippling, Pave, Lattice, etc.). - Prior partnership with Finance on headcount planning and compensation modeling. - Background in companies that value craft, operational rigor, and high standards. WHY THIS ROLE MATTERS This is a foundational leadership role at a true inflection point. The systems, standards, and cultural norms you put in place will directly shape: - Who we hire - How we reward performance - How managers lead - How fairly and clearly people experience Numeral as we scale If you’re excited by high‑growth, high‑ownership environments — and want to build a People function that’s respected as a core business partner — we’d love to talk. WHAT WE OFFER - Competitive salary and equity - you'll share directly in the company's success - Full medical, dental, and vision coverage - Wellness perks like Headspace and the Peloton One App - 401(k) to help you build long-term financial security - Lunch and snacks when you're in the office - Regular team off-sites and company events as we grow - A culture built on ownership - your work matters and people will see it!