Ceo jobs in Canada

Gruntwork, the company behind Terragrunt, is on a mission to transform the way DevOps is done. Let’s face it: 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.

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 a 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.

• You’re the companies product person for the near term, that means you operate at all levels of the product stack.

• 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.

• The company does not, for now, have a dedicated product marketing headcount, so that responsibility primarily will fall with the product lead, to be shared with our head of marketing.

• Design, implement, and 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, with a heavy focus 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.

• We have several developers who work everyday with the Terragrunt, Terratest, Opentofu (and other) open source communities. You’re job is to make sure that our 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 (open source and commercial).

• 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.

We’re looking for a Grunt who:

• Is an open‑source commercialization veteran: You have a proven and demonstrable track record of building a successful commercial, product‑led growth (PLG) motion on top of a popular open‑source project. You know how to earn community trust while building a scalable business.

• Is a developer‑focused product leader: You have extensive experience leading Product Management, Product Marketing, and/or Developer Relations functions for a highly technical B2B SaaS or DevOps product. You live and breathe the developer user journey.

• Is a strategic thinker & gifted storyteller: You can zoom out to see the big picture and craft a compelling, simple narrative, but you can also zoom in to obsess over the details of a user flow. You can articulate a complex vision to investors, customers, and developers with equal clarity and passion.

• Is an ecosystem navigator: You understand how to build leverage through partnerships and have experience working within a major cloud ecosystem (AWS is heavily preferred).

• Loves making customers happy. You're on a mission to making customers happy and successful. You're eager to leverage your talents to meet their needs.

• Loves a challenge. You like to perform at your best by aiming high while also taking care of yourself and those around you.

• Cares about your fellow humans. You look to make personal connections with the people you work with, and you want to work for a company whose mission and people you believe in.

• Has extensive Terraform/OpenTofu/Terragrunt experience. You have directly authored plenty of OpenTofu/Terraform/Terragrunt modules, you've operated or been highly adjacent to IaC in prod and can speak from your years of experience.

• Has a passion for DevOps best practices. You're passionate about the best way to run modern cloud infrastructure in a secure, convenient, and enjoyable way.

• No investors, no debt. We control our own destiny and are focused on building a company that customers love.

• 100% remote. We've been 100% remote from day 1, however we're all in USA time zones and regularly collaborate together.

• In‑person meetups every few months. We meet in person every ~4 months in a beautiful location to foster close relationships among our team.

• Transparent financials. We share our full financials every month with every member of the company.

• Systematically above‑market salary. We compute all salaries using a formula designed to systematically pay above market, wherever you live.

• Above‑market equity. We offer above‑market equity grants, and we’ve even put in place a “progressive equity” plan where if there is a large exit event, employees end up with a progressively larger portion of the proceeds than their pro‑rata equity holdings.

• Profit‑sharing bonus. We set aside a pot of money at the end of each year based on profits and distribute bonuses according to a formula that uses as inputs your level within the company and the length of your tenure at the company.

• Hardware budget. We'll buy you a brand new state‑of‑the‑art 16" Apple MacBook Pro (or other computer of your choosing of equivalent value) upon joining. It will be owned by you, not the company.

• Personal budget. We'll give you a personal budget of $1,000 USD per month (yes, per month) to spend on your workspace (e.g., a co‑working space), health (e.g., gym, yoga), time (e.g., babysitter), and/or learning (e.g., books, courses).

• Medical/Dental/Vision insurance. We offer a range of high‑quality plans with a large portion paid by the company. For countries other than the US, this includes extra coverage on top of your statutory insurance.

• Pension/401(k) contributions. We contribute 3% of your salary to your pension or 401(k).

One of our values is that work‑life balance leads to both better work and a better life, so we require that all our team members live in a time zone between Los Angeles and New York, inclusive. You can be located anywhere in the western hemisphere, though most of our team is in the USA and Canada.

Our philosophy for the interviewing process for this role:

• Zero Fluff: Every interview will test a specific competency (Technical, Strategic, or Cultural).

• The "Doer" Filter: The process is front‑loaded to identify candidates who excel at writing PRD and talking to customers

• Asynchronous Respect: Since we are a remote‑first, written‑culture company, a portion of the process will involve written communication.

After you apply for this role, here's the process we'll go through to evaluate a mutual fit:

1. Phone screen: We'll do a quick phone screen to assess a general fit.

2. The Product Builder Screen: We’re looking to make sure you’re comfortable being “in the weeds” building product.

3. Technical Deep Dive: Validating technical fluency and end user (developer, architect) empathy.

4. Messaging Deep Dive: Chat with our head of marketing and sales about the product marketing elements of the role

5. Take Home: We’ll ask you to think a bit about a product strategy problem and draft some thoughts process on a real‑world Gruntwork problem.

6. Take Home Review + “Grunt” Culture fit. We'll start by reviewing your work on the take home, and then get a feel for your alignment to Gruntwork’s values

7. Reference checks. We'll ask your prior colleagues about where you thrive most.

8. Offer! We're very pleased to be working together!

• Great: Can articulate exactly why a developer would swipe a credit card for Scale vs. stay on OSS.

• Not Great: Thinks "PLG" just means "add a free trial button.”

• Great: Can write a Terraform snippet or explain terragrunt run‑all mechanics.

• Not Great: Talks about "Cloud" in buzzwords; cannot differentiate between IaC and PaaS.

• Great: Excited to write the docs, PRD, the blog post, and the Linear ticket.

• Not Great: Asks "What is the budget for hiring a Junior PM?”

• Great: Speaks in terms of TAM, CAC, and NRR (Net Revenue Retention).

• Not Great: Focuses only on features, ignores the business model.

• Great: Protects the Open Source community; treats them as partners, not just leads.

• Not Great: Views the Open Source users as "freeloaders" to be monetized aggressively.

Compensation Range: $180K - $235K