Head of People

Location: New York City | Full-time | In-office (Mon–Fri)

About RepRally:

Across the U.S., there are more than 500,000 independent stores—gas stations, convenience stores, bodegas, local markets—that each generate $1-3M in annual sales yet operate without modern tools or data.

RepRally is building the next-generation distribution network for this market. We help brands reach these stores and help store owners buy smarter. Our platform maps and analyzes every store in the country, identifies what products fit local demand, and connects them directly to the right brands and sales reps.

Brands gain clear CAC-to-LTV visibility and efficient access to thousands of retail points. Stores get intelligent assortment recommendations powered by insights from thousands of similar locations, turning raw data into real decisions on what to stock and sell.

We've already won with thousands of stores, 500 brands, hundreds of reps nationwide, are backed by Greylock, and built by founders and marketplace operators from top startups. We're scaling rapidly and preparing for our next stage of growth.

The Role:

We’re looking for a Head of People who loves to build, someone who gets excited by blank-slate environments and thrives on turning ambiguity into structure.

In this role, you’ll architect the systems that define how talent is attracted, hired, onboarded, developed, retained, and separated. You will lead Talent Acquisition and People Operations, shaping the entire employee lifecycle and building the recruiting function from the ground up.

You will partner closely with founders and leaders to understand evolving business priorities, diagnose talent gaps, and design scalable people frameworks that drive performance, culture, and accountability.

This role is ideal for a strategic operator and talent leader who can zoom out on org design and talent strategy while rolling up their sleeves to build foundational systems.

What You’ll Do:

• Talent Strategy & Leadership: Own talent acquisition end-to-end: defining hiring priorities, building a recruiting engine, partnering with leaders on org design and capability gaps, and scaling a hiring team to deliver a differentiated candidate experience.
• People Operations Architecture: Design and operationalize scalable people systems across onboarding, HRIS, benefits, performance, and employee experience, owning the tools and workflows that enable discipline and future team expansion.
• Employee Lifecycle Ownership: Architect the full employee journey - from offer and onboarding through development, recognition, and transition/offboarding - building frameworks, feedback loops, and cultural programs that drive growth and productivity.
• Compliance & People Risk Management: Ensure compliant hiring, employment practices, payroll, benefits, and documentation across multi-state W-2 and contractor populations by partnering with Legal and Finance to manage risk and governance.
• People Insights & Accountability: Use people metrics and reporting to drive decision-making and leader performance, coaching teams to improve efficiency, feedback quality, and equitable talent outcomes.
• Team Building: Build and eventually lead a high-performing People team - including recruiting, people operations, and EA/support roles - to scale the function as the company grows.

What You Bring

• 4–6 years of experience in People Ops or Talent Acquisition in a fast-paced startup environment
• Track record of building and scaling talent systems, not just maintaining them.
• Skilled in diagnosing organizational needs, designing processes, and operationalizing change.
• Strong understanding of employment compliance and multi-state workforce dynamics (W-2 and 1099 mixed models a plus).
• Experience leading high-impact recruiting efforts or talent teams.
• A builder: comfortable in ambiguity, decisive in structure, excellent at execution.
• A cultural connector: empathetic, trusted, and comfortable with accountability and high standards.
• Based in NYC (Mon-Fri) and energized by an in-office culture.

Bonus experience:

• Experience with gig or distributed workforces
• Familiarity with workflow automation tools (n8n, Zapier) or HRIS integrations
• Background in culture architecture, leadership enablement, or internal communications.

Why Join RepRally:

• Build the People & Talent foundation at a fast-growing, venture-backed startup
• Build and own the systems that power our culture, performance, and employee experience
• Partner directly with founders and leaders to design how we attract, onboard, and grow top talent
• Create scalable processes for a hybrid, multi-state team of full-time employees and contractors
• Join a team that moves fast, values transparency, and invests deeply in its people
• Backed by Greylock, Infinity, and Indicator Ventures, with strong momentum heading into Series B
• High-visibility role in the heart of NYC, working cross-functionally across every part of the company