Head of People

Numeral is building the automation backbone for internet commerce — starting with the painful world of sales tax compliance. We handle everything from registration to remittance, delivering a white-glove service so e-commerce businesses can stay laser-focused on what they do best: growing their products, customers, and teams.

We’re one of the fastest-growing companies from Y Combinator’s W23 batch, backed by top-tier investors including Benchmark Capital. Our team has deep roots from the early days at Stripe, Airbnb, Notion, and other breakout companies — and now we’re bringing that same level of craft, speed, and ambition to a space that’s long overdue for reinvention.

Numeral is small but mighty. Growth is already borderline unmanageable — which means every hire we make now will directly shape the trajectory of the company. If you’re excited about joining as an early team member and want the kind of ownership that defines careers, we want to meet you.

Running an online business today means wearing a thousand hats — most of them not the reason founders started their company. Our mission is to eliminate the administrative and accounting burdens that distract businesses from doing what they love.

We’ve already helped hundreds of merchants avoid the headache of building giant finance teams just to manage tax compliance. Tomorrow, we’re scaling that impact even further: building the automation layer that lets internet businesses stay nimble, compliant, and future-proof.

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.

• 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.

• 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.

• 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.

• 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.

• 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).

• 10+ 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.

• 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.

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.