Rollstack is creating a new category in the modern data stack: Report Automation. We connect BI tools to slide decks and documents, automating their generation and updates, and effectively solving the last-mile problem of data presentation.

About the Company

At Rollstack, we are revolutionizing the way businesses share and communicate data and insights. Organizations worldwide rely on slide decks and documents to make informed decisions, whether for leadership, clients, or partners. Yet, preparing these materials often consumes countless hours. Rollstack fully automates that.

We help some of the world's leading organizations—from mid-sized to public companies like SoFi, Zillow and Whirlpool—in automating their slide decks and documents. Headquartered in New York, we offer a remote-friendly workplace and are backed by Insight Partners and Y Combinator, the most successful startup incubator in the world that produced the likes of Airbnb, Twitch, Instacart, Dropbox, Reddit, Doordash, Stripe, Coinbase, etc.

Our team operates with speed and focus to deliver outsized impacts for our customers. We approach every challenge with first principles, never assuming things have to be done a certain way. We are a diverse team that believes intelligence and kindness go hand in hand, welcoming individuals from all backgrounds. Our persistence and rapid execution define us as a category leader and a future generational company.

About the Role

We're looking for a hands-on Head of Talent & People Ops to help us scale Rollstack's world-class team across Engineering, Product, and Go-To-Market. You’ll lead both talent acquisition and people operations at a critical growth stage of the company. This is a foundational role for someone who knows how to operate in fast-paced, early-stage environments and understands what it takes to attract and retain top talent including world-class engineers.

What You Will Do

• Own and scale the entire recruiting process, from job definition and sourcing to closing across all functions
• Lead mid to senior-level hiring across Engineering, Product, Design, and GTM
• Design and manage structured interview processes to ensure speed, fairness, and high signal
• Build a repeatable hiring engine that attracts exceptional talent and supports hypergrowth
• Partner with the leadership team on headcount planning, compensation strategy, and team org design
• Lead People Ops initiatives including onboarding, performance frameworks, remote culture, and compliance
• Implement and manage the HR tech stack and processes that support a remote-first team
• Serve as a strategic thought partner on team structure, culture, and scaling challenges

Who We Are Looking For

• 5–8+ years of experience in talent recruiting or people leadership roles at high-growth startups
• A track record of hiring exceptional engineers, and GTM talent
• Experience with state-of-the-art tools and hiring stack
• Strong familiarity with early-stage hiring playbooks and fast-paced environments
• Fluency in startup org structures, compensation strategy, and equity norms
• Strong project management and communication skills
• Passion for building and scaling inclusive, high-performance cultures

Why Join Us

• Join a Y Combinator-backed company that’s transforming how people — from your friends and family to teams worldwide — work more efficiently.
• Collaborate with an exceptional team, including alums of companies like Amazon, Pinterest, Tesla, Nvidia, and AiFi.
• Enjoy a fully remote and diverse workplace.
• Join a world-class product and engineering team with a product that sells itself.
• Participate in bi-annual team offsites at dream destinations from your travel bucket list.
• Earn a competitive pay and life-changing equity at a fast-growing, high-efficiency startup.