Principal Customer Success Manager

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, profitable 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 Customer Success Manager (CSM) to ensure the success of our most strategic customers and drive the next phase of our 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 deep relationships with Fortune 2000 companies and shape the future of customer success at Gruntwork.

What You'll Do

• Own the Customer Lifecycle: Act as the primary point of contact for strategic accounts, ensuring their success from onboarding to adoption, expansion, and renewal.

• Net Retention: Partner with Sales to drive expansion opportunities and improve net revenue retention (NRR).

• Drive Value Realization: Partner with customers to define success metrics, identify use cases, and deliver measurable outcomes using Gruntwork’s DevOps Foundation platform.

• Build Strategic Relationships: Develop trusted relationships with CTOs, VPs of Engineering, and DevOps leaders to understand their goals and align Gruntwork’s solutions to their needs. This includes leading strategic executive business reviews (EBRs/QBRs) to align on business outcomes, showcase ROI, and ensure long-term partnership growth

• Mitigate Risk: Proactively monitor customer health, identify risks, and develop action plans to prevent churn and ensure long-term success for our platform and legacy customers.

• Influence Product Direction: Serve as the voice of the customer, sharing insights and feedback with product and engineering teams to inform roadmap decisions.

• Shape Customer Success Strategy: Contribute to the evolution of Gruntwork’s customer success programs, including onboarding, training, and enablement initiatives.

What You Bring

• 8+ years of experience in customer success, account management, or technical consulting, with a proven track record of managing enterprise-level accounts in a SaaS or infrastructure-focused company.

• Technical Expertise: Strong understanding of cloud infrastructure (AWS, Azure, GCP), DevOps practices, and infrastructure-as-code (IaC) tools like Terraform.

• Strategic Mindset: Ability to think strategically, identify growth opportunities, and develop long-term customer success plans.

• Exceptional Communication Skills: Excellence in building trust and rapport with executive stakeholders and technical leaders.

• Problem-Solving Skills: A proactive and solutions-oriented approach to addressing complex customer challenges.

• Data-Driven Approach: Comfortable using data to track customer health, measure success, and inform strategic decisions.

• Leadership Experience: Proven ability to mentor and guide team members, fostering collaboration and driving results.

Why You'll Love It Here

• Incentives for Net Expansion: The more customers love Gruntwork, the more you’ll be rewarded.

• Impact: Play a key role in shaping the success of our customers and the future of cloud infrastructure.

• Growth: Work in a fast-growing company with opportunities for professional development and career advancement.

• True Work-Life Balance: 100% remote work in a high-trust environment (US & Canada time zones).

• Uncapped Earnings Potential: Competitive base salary, performance-based bonuses, and above-market equity + progressive equity plan that can double your equity.

• Full Company Support: 1:1 resourcing from Marketing, Sales, and Solutions Engineering teams.

• Personal Budget: $1,000 USD monthly budget for workspace, health, and learning.

• Regular In-Person Meetups: Team gatherings in beautiful locations (New Orleans is up next).

• Profit-Sharing Bonus: Based on company performance.

• Opportunity to Shape DevOps: