Principal Enterprise Account Executive

About Gruntwork

Gruntwork is on a mission to transform the way DevOps is done. We are globally recognized both for our open-source tools used by thousands of companies from startups to Fortune 500s, and our thought leadership on how DevOps should be done. As a bootstrapped company with no investors or debt, we control our own destiny and are focused on building a company that customers love.

The Opportunity

We're seeking an exceptional Principal Enterprise Account Executive to drive our next phase of growth. This is a rare opportunity to join a category-defining company at the intersection of DevOps and enterprise infrastructure, where you'll have the autonomy to build and execute strategic relationships with Fortune 2000 companies.

What You'll Do

• Own the full sales cycle for enterprise accounts ($100K-$1M+ deals), from strategic prospecting to close

• Partner with Solutions Engineers to architect and present complex technical solutions to CTOs, VPs of Engineering, and DevOps leaders

• Build and execute account strategies that drive adoption of our DevOps Foundation platform across large organizations

• Influence product direction and go-to-market strategy through deep customer relationships and market insights

• Help shape the future of our enterprise sales motion as a key member of our growing team

What You Bring

• 8+ years of enterprise software sales experience, with a proven track record of consistently exceeding quota ($1.5M+ annually)

• Deep experience selling technical infrastructure solutions to engineering leaders

• Strong understanding of open-source, cloud infrastructure, DevOps practices, and modern software development

• Strategic mindset with ability to navigate complex organizational structures and build consensus among diverse stakeholders

• Excellence in solution selling, pipeline management, and accurate forecasting

• A book of business and relationships in the DevOps industry, including customers and partners

Why You'll Love It Here

• Uncapped earnings potential with competitive base salary, commission, 1.5x acceleration above quota and above-market equity

• Full company support including 1:1 resourcing from Marketing, Account Development and Sales Engineering

• True work-life balance in a 100% remote in a high-trust environment (US & Canada time zones)

• $1,000 USD monthly personal budget for workspace, health, and learning

• Regular in-person team meetups in beautiful locations (New Orleans is up next)

• Profit-sharing bonus program based on company performance

• Opportunity to shape the future of DevOps alongside industry thought leaders

We’re Looking for a Grunt Who

• 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 to learn. You're excited abut learning new things, and looking to be at the forefront of Sales and DevOps best practices.

• 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 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.

Our Interview Process

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. Values & Skills. We'll talk shop with you to see if we're on the same page about culture and sales skills.

3. Trial Project: We'll pay you for the opportunity to work together for a day, focused on developing a territory plan and showing us your sales swing in a role play.

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

About Our Team

You'll join a close-knit, high-performing team that values autonomy, continuous learning, and doing what's right for customers. We believe in sustainable growth, thoughtful decision-making, and building for the long term.

• 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).