Base Pay Range
$180,000.00/yr - $235,000.00/yr
About Gruntwork
Gruntwork, the company behind Terragrunt, is on a mission to transform the way DevOps is done. Designing, launching, and managing infrastructure is still a terrible experience for most organizations, but it doesn’t have to be that way! We are globally recognized both for our open source tools (Terragrunt, Terratest, cloud-nuke) used by thousands of companies from startups to Fortune 500s, and our thought leadership on how DevOps should be done.
Our commercial offerings include:
- Gruntwork AWS Accelerator: An opinionated, best‑practices solution that accelerates a company's journey to a secure, compliant, and well‑architected IaC setup on AWS.
- Terragrunt Scale: A suite of enterprise‑grade tools including our IaC Pipeline, Patcher, and Drift Detection to help organizations manage IaC at scale.
Gruntwork is a profitable, bootstrapped company without any outside investors. We operate as a lean, capital efficient startup and our team is made up of values‑aligned, hard‑working and independently capable individuals.
About This Role
Gruntwork presents the perfect opportunity for experienced product lead to scale an OSS PLG product. Terragrunt has huge adoption (hundreds of thousands of developers), significant positive brand equity, and has had minimal to no commercialization to date. We’re aiming to build a collaborative and respectful commercial motion around the product. If you’ve seen this pattern before and similarly see the potential, this could be the perfect opportunity for you.
We are seeking a strategic, hands‑on Head of Product to own the unified vision and execution for our product management (and to an extent, product marketing) functions. This is not a management and delegation role; this is an in‑the‑weeds product role with both strategic and operational components. You’ll be working directly with open‑source users, open‑source community contributors and our in‑house R&D team to build the future of DevOps.
Responsibilities
Product Strategy & Product Execution
- Operate at all levels of the product stack as the company’s product person for the near term.
- Define and own the company's product vision, strategy, and roadmap, ensuring tight alignment with our overall business goals and fundraising narrative.
- Collaborate with the CEO and engineering leadership to translate the company vision into a clear, prioritized roadmap for both the AWS Accelerator and Terragrunt Scale.
- Lead market research and customer discovery to sharpen our products’ value proposition, focusing on specific, high‑pain use cases like security and compliance frameworks (e.g., SOC 2, HIPAA, FedRAMP).
- Spearhead the ideation and prototyping of a future AI‑powered offering that leverages our unique data and expertise in the IaC space.
Product Marketing
- Own the PLG strategy, creating seamless and intuitive pathways for open‑source users to discover, try, and buy our commercial products.
- Develop compelling product positioning, messaging, and go‑to‑market strategies that resonate deeply with our technical audience, from individual developers to enterprise decision‑makers.
- Mastermind our partnership and ecosystem strategy, focusing heavily on leveraging the AWS Marketplace, co‑selling with AWS, and building relationships with key ISVs.
- Own product pricing, packaging, and lifecycle management for all commercial offerings.
Developer Relations & Community
- Ensure the product strategy remains supportive of, and sensitive to, the concerns and priorities of open‑source communities.
- Nurture and grow the vibrant communities around Terragrunt and OpenTofu, ensuring Gruntwork remains a trusted, authentic, and respected leader.
- Act as the voice of the community internally, channeling user feedback, pain points, and insights directly into the product development process.
- Empower the developer community through world‑class documentation, examples, tutorials, and content that showcases the power of our entire ecosystem (open source and commercial).
Leadership & Team Building
- Foster a culture of customer obsession, data‑driven decision‑making, and rapid iteration.
- Serve as a key member of the executive team, contributing to fundraising efforts, board meetings, and overall company strategy.
About You
- Open‑source commercialization veteran: Proven track record of building a successful commercial, product‑led growth motion on top of a popular open‑source project.
- Developer‑focused product leader: Extensive experience leading Product Management, Product Marketing, and/or Developer Relations functions for a highly technical B2B SaaS or DevOps product.
- Strategic thinker & gifted storyteller: Ability to craft a compelling, simple narrative while also obsessing over user‑flow details.
- Ecosystem navigator: Experience building leverage through partnerships and working within a major cloud ecosystem (AWS preferred).
- Loves making customers happy and is mission‑driven to support their success.
- Loves challenges and strives for high performance while caring for self and colleagues.
- Values personal connections and works for a mission‑aligned company.
- Extensive Terraform/OpenTofu/Terragrunt experience, having authored modules and lived IaC in production.
- Passion for DevOps best practices and running modern cloud infrastructure securely and conveniently.
About the Company
- No investors, no debt, and full control of our destiny.
- 100% remote from day 1 with a focus on U.S. time zones.
- In‑person meetups every ~4 months in a beautiful location.
- Transparent financials shared monthly with all employees.
- Systematically above‑market salary and progressive equity plan.
- Profit‑sharing bonus and hardware budget (new 16″ Apple MacBook Pro or equivalent).
- Personal budget of $1,000 USD per month for workspace, health, and learning.
- Medical/Dental/Vision insurance with large company contribution; extra coverage abroad.
- 3 % pension/401(k) contribution.
Time Zone
Candidates must live in a time zone between Los Angeles and New York, inclusive. Remote location in the western hemisphere is acceptable, though most of our team is in the U.S. and Canada.
Interview Process
Our philosophy for this role:
- Zero Fluff: Every interview tests a specific competency (Technical, Strategic, or Cultural).
- The "Doer" Filter: Process focuses on writing PRDs and talking to customers.
- Asynchronous Respect: Written communication is key for this remote, written‑culture company.
Process:
- Phone screen: Quick assessment of fit.
- Product Builder Screen: Evaluate "in‑the‑weeds" product building.
- Technical Deep Dive: Validate technical fluency and developer empathy.
- Messaging Deep Dive: Discuss product marketing elements with head of marketing and sales.
- Take‑home: Produce a product‑strategy brief.
- Take‑home review & cultural fit: Review from Grunt and assess alignment with values.
- Reference checks.
- Offer: We’re pleased to work together!
Sample Scorecard
PLG Strategy
- Great: Articulates exactly why a developer would pay for Scale vs. staying on OSS.
- Not Great: Thinks "PLG" means only adding a free trial button.
Technical Skill
- Great: Can write a Terraform snippet or explain terragrunt run‑all mechanics.
- Not Great: Talks about "cloud" buzzwords without differentiating IaC vs. PaaS.
Execution
- Great: Excited to write docs, PRD, blog posts, and Linear tickets.
- Not Great: Asks about the budget for hiring a Junior PM.
Business Acumen & Strategy
- Great: Speaks in terms of TAM, CAC, and NRR (Net Revenue Retention).
- Not Great: Focuses only on features, ignores the business model.
Empathy
- Great: Protects the Open Source community and treats them as partners.
- Not Great: Views the Open Source users as "freeloaders" to be monetized aggressively.