Technical 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 Technical Customer Success Manager (TCSM) 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 Post-Sales Customer Relationships

• Own the Customer Lifecycle: Act as the primary point of contact for strategic accounts, ensuring their success from onboarding to adoption, expansion, and renewal.
• Accountable for Net Retention: Own the renewals process. Partner with Sales to drive expansion opportunities and drive net retention.
• Drive Value Realization: Partner with customers to define success metrics, identify use cases, and deliver measurable outcomes using Gruntwork’s 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/CABs) to align on business outcomes, showcase ROI, and ensure long-term partnership growth.
• Create and manage a Customer Advisory Board: Facilitate the creation of a semi-annual CAB with our top customers.

Own the Success function Back Office

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

Become a champion of Gruntworks' products

• Be a Gruntwork Expert: On a technical level, understand how each of Gruntwork's products provides value to customers and use that knowledge to help customers see value, or upsell/cross-sell to products that can provide additional value
• Champion the Customer to the Company: Serve as the voice of the customer - bring customer feedback and concerns back to the team to prioritize fixes and influence the roadmap.

What You Bring

Gruntwork is a small team, and for now we're a customer success department of one. You'll be both strategic and operational -- on any given day being both customer facing and running internal projects. To be successful, expect to wear many hats and to bring:

• 6+ 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.
• 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 both internally and externally.
• Project Management Skills: Ability to define requirements to either improve internal success SOPs or operational capabilities, or for external PoCs/trials with customers.
• Problem-Solving Skills: A proactive and solutions-oriented approach to addressing complex customer challenges.
• Technical Expertise: Strong understanding of cloud infrastructure (AWS, Azure, GCP), DevOps practices, and infrastructure-as-code (IaC) tools like Terraform.
• Detail Orientation: Consistent focus on the small things that can make a difference either to the customer, or in our internal processes.
• Data-Driven Approach: Comfortable using data to track customer health, measure success, and inform strategic decisions.
• Startup Compatible, Hands-On Attitude: Proven ability to roll up your sleeves and get your hands dirty, we want someone with a bias for action.
• (Bonus) SQL Skills: Work with the team to use the data at our disposal and make it useful for customer success.

Why You'll Love It Here

• Commission-Based OTE: The more customers love Gruntwork, the more you’ll be rewarded.
• 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 wellness -- workspace, health, and learning.
• Regular In-Person Meetups: Team gatherings in beautiful locations (Mexico City is up next!).
• Profit-Sharing Bonus: Based on company performance.
• Opportunity to Shape DevOps: Work alongside industry thought leaders to define the future of DevOps.

We’re Looking For a Grunt Who

• Loves making customers happy. You're on a mission to ensure customers are successful and delighted with Gruntwork’s solutions.
• Loves to learn. You're excited about staying at the forefront of DevOps best practices and customer success strategies.
• Loves a challenge. You thrive in high-stakes environments and are motivated by solving complex problems.
• Cares about your fellow humans. You build strong personal connections with customers and colleagues alike.
• Has a passion for DevOps best practices. You're passionate about helping customers run modern cloud infrastructure in a secure, scalable, and efficient way.

Our Interview Process

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

• Phone Screen: We'll do a quick phone screen to assess a general fit.
• Client-Facing Skills Screen: We'll role play and talk shop about your customer-facing wins and losses.
• Values: We'll cover Gruntwork's values and discuss your background applying similar values at prior experiences
• Backoffice Skills: You'll talk with members of our team about what it takes to efficiently run a customer success operation, including CRM workflows, CRM data hygiene and customer success reporting.
• Technical Depth: We'll talk high level about DevOps, infrastructure as code and software delivery at enterprise. This is a conversation, there's no coding or coding questions, we promise.
• Trial Project: We'll pay you for the opportunity to work together for a day, focused on developing a customer success plan for a strategic account.
• 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