Head of Product

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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 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 the 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 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 & Execution

• Own the company's product vision, strategy, and roadmap, ensuring 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 company’s 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 on 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 product strategy is supportive of, and remains sensitive and empathetic to the concerns and priorities of open source.
• Nurture and grow the vibrant communities around Terragrunt and OpenTofu, ensuring Gruntwork remains a trusted, authentic, and respected leader in the space.
• 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.

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 with a proven track record of building a successful product‑led growth motion on top of a popular open‑source project.
• Developer‑focused product leader with 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 who can craft a compelling, simple narrative while obsessing over the details of a user flow.
• Experienced in building leverage through partnerships and working within a major cloud ecosystem (AWS preferred).
• Passionate about making customers happy and meeting their needs.
• Enjoys challenges and aims high while caring for themselves and others.
• Values personal connections and works for a company whose mission and people they believe in.
• Extensive Terraform/VPM/OpenTofu/Terragrunt experience with deep IaC expertise.
• Passion for DevOps best practices.

About the Company

• No investors, no debt. Control our own destiny and focus on building a company customers love.
• 100 % remote, all in USA time zones, with regular collaboration.
• In‑person meetups every ~4 months in beautiful locations.
• Transparent financials shared monthly with all members.
• Systematically above‑market salary using a formula that pays above market.
• Above‑market equity grants with a progressive equity plan for large exit events.
• Profit‑sharing bonus based on company profits, level, and tenure.
• Hardware budget for a new state‑of‑the‑art MacBook Pro (or equivalent).
• Personal budget of $1,000 USD per month for workspace, health, time, and learning.
• Medical/Dental/Vision insurance with high coverage.
• Pension/401(k) contributions: 3 % of salary.

About Your Time Zone

Work‑life balance leads to better work and life. All team members must live in a time zone between Los Angeles and New York, inclusive. Location can be elsewhere in the western hemisphere, though most team is in the USA and Canada.

Interview Process

• Zero Fluff: Every interview tests a specific competency (Technical, Strategic, or Cultural).
• Doer Filter: Front‑loaded process to identify candidates who excel at writing PRD and talking to customers.
• Asynchronous Respect: A portion of the process involves written communication.

After you apply, the process includes:

• Phone screen.
• The Product Builder Screen.
• Technical Deep Dive.
• Messaging Deep Dive with head of marketing and sales.
• Take Home strategy exercise.
• Take Home Review and cultural fit discussion.
• Reference checks.
• Offer.

Sample Scorecard

PLG Strategy

• Great: Articulate exactly why a developer would pay for Scale vs. stay on OSS.
• Not Great: Thinks "PLG" just means adding a free trial button.

Technical Skill

• Great: Write a Terraform snippet or explain terragrunt run‑all mechanics.
• Not Great: Talks about "Cloud" buzzwords; cannot differentiate IaC and PaaS.

Execution

• Great: Excited to write docs, PRD, blog post, and Linear tickets.
• Not Great: Asks "What is the budget for hiring a Junior PM?"

Business Acumen & Strategy

• Great: Speaks in terms of TAM, CAC, and NRR.
• Not Great: Focuses only on features, ignores business model.

Empathy

• Great: Protects the Open Source community; treats them as partners.
• Not Great: Views the Open Source users as freeloaders to be monetized aggressively.

Compensation Range

$180,000 – $235,000

Seniority Level

Executive

Employment Type

Full‑time

Job Function

Product Management and Marketing

Industries

Software Development

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