About Gumroad
Gumroad is an e-commerce platform that empowers creators to sell digital products directly to their audience, from art and ebooks to courses and communities. Founded in 2011, Gumroad has facilitated over $1 billion in creator earnings. Operating with a lean, highly efficient team, the company embraces a minimalist and transparent approach to both product and culture. In 2025, Gumroad made headlines by open-sourcing its entire codebase, which exemplifies its commitment to decentralization and community collaboration.
Flexile is a product from the Gumroad team that allows companies to process compensation and dividend payments in a single platform.
Gumroad Values
- Empowerment Through Autonomy: Minimal meetings and deadlines. The team is managed by results.
- Transparency: Gumroad openly shares its roadmap, decisions, and even financials with the public.
- Creator-First: Every product decision serves the mission of maximizing how much creators earn.
- Remote-First: Team members work globally, on their own schedules, with minimal management overhead.
- Sustainability: Lean, profitable, and purpose-driven. The company values long-term impact over flashy growth.
About the Role
We’re looking for a Senior Fullstack Engineer to join the small but mighty engineering team at Gumroad and Flexile. In this role, you’ll work closely with Ershad Kunnakkadan (Staff SWE) and address the needs of Gumroad and Flexile’s product initiatives, including open-source platform improvements and community-first feature rollouts.
You’ll be entrusted with owning major technical initiatives across the backend and frontend — from evolving a mature Ruby on Rails application to building scalable APIs, integrating with AWS, and working collaboratively across a lean, async-first organization.
About You
You thrive in highly autonomous environments and enjoy solving complex backend challenges and frontend projects. You take initiative, ship high-quality code, and enjoy the craft of engineering. You may have strong opinions about code structure, but you’re not dogmatic; pragmatism and impact matter most.
You’re someone who can collaborate effectively with peers across different time zones, without needing hand-holding or micromanagement.
Skills
Required Hard Skills:
- English (C1+ proficiency)
- 7+ years of experience in Ruby on Rails
- 2+ years of experience in React
- Proficient in building and maintaining APIs
- Experience with AWS infrastructure
- Ability to work asynchronously with GitHub-based workflows
Great to have:
- Strong command of databases (PostgreSQL)
- Modern frontend tooling: Vercel, Next.js, Tailwind, TypeScript
- Contributions to open-source projects
- Experience working on or with creator-focused platforms
Nice to have:
- Exposure to DevOps workflows and infrastructure scaling
- Strong UI/UX intuition despite backend focus
- Demonstrated product taste the ability to think through the user impact of engineering decisions
Required Soft Skills:
- Highly self-directed and accountable
- Highly motivated to be a top producer
- Comfortable working without traditional management layers
- Product thinking and performance sensitivity
Role Responsibilities
- Collaborate with Ershad and the broader team on backend initiatives
- Write clean, scalable Ruby code that powers mission-critical workflows
- Improve and evolve the open-source Gumroad platform
- Maintain and optimize AWS-based infrastructure
- Contribute to the performance and reliability of payment and community features
- Participate in async code reviews, GitHub issues, and documentation
Compensation & Benefits
- $84,000 – $96,000 per year
- Stock options in Gumroad
- Fully remote role with flexible hours
- Minimal meetings
- Work with a globally distributed, high-performing team
- Opportunity to build for millions of users in the creator economy
- Quarterly offsites
- Keepers perks:
- MacBook Pro provided
- Premium tools (Grammarly, Masterclass, etc.)
- Bi-monthly payments
- Legal + accounting setup advisory for CNPJ
- Dedicated Team Success Manager for ongoing support
Selective Process
- Apply (closed)
- Interview with Keepers
- 2-3hr Technical deep dive with Ershad Kunnakkadan (Staff SWE)
- Optional: Have a faster Technical Deep Dive interview by contributing to open source projects: Gumroad, Flexile, or Helper at github.com/antiwork
- Final conversation with Sahil Lavingia (Founder & CEO)