Assistant Remote Open Source Intelligence Jobs in Chicago, IL

As vCluster Labs’ Enterprise Account Executive, you aren’t just selling software; we are defining a category. In this role, you will be the CEO of your territory, tasked with identifying, navigating, and closing large-scale agreements with the world's leading organizations. You will be selling a technical platform that solves critical problems for Engineering, DevOps, Security, and Data leaders.

As an Enterprise Account Executive, your role will include:

• Strategic Territory Management: Own a dedicated patch of Enterprise accounts. Build a comprehensive territory plan to uncover new opportunities and expand existing footprints.

• Full-Cycle Execution: Manage the entire sales lifecycle from prospecting and discovery to negotiation and close. You are a "Hunter" who enjoys the thrill of the chase but executes with the precision of a consultant.

• Multi-Threaded Selling: Navigate complex organizations to build consensus across technical champions (Dev/Ops/Security practitioners) and executive economic buyers (CTO, CIO, CISO, CFO).

• Value Engineering: Move beyond feature/function selling. articulate a clear "Business Value Assessment" (BVA) that ties our technical capabilities to the customer's top-line revenue or bottom-line efficiency.

• Methodical Forecasting: Maintain hygiene in Salesforce/CRM. Utilize MEDDPICC or Command of the Message methodologies to provide accurate weekly, monthly, and quarterly forecasts.
  

This role could be a fit for you if you bring:

• Experience: 7+ years of quota-carrying field sales experience, with at least 3+ years selling specifically to the Enterprise ($200k - $1M+ ACV).

• Technical Aptitude: You don’t need to code, but you must be "technically fluent." You can hold your ground in a conversation with a VP of Engineering or a Chief Architect about their tech stack, workflow, and pain points.

• Methodology Master: You live and breathe sales methodology. You can clearly explain how you use MEDDPICC/MEDDIC to qualify deals and de-risk your pipeline.

• Consistency: A documented history of performing in the top 10-20% of your cohort. We want to see President’s Club awards and consistent quota over-achievement.

• Start-Up Grit: Experience working in a high-growth environment (Series B to IPO phase). You are comfortable with ambiguity and are willing to build the playbook, not just read it.
  

Bonus points for:

• Domain Expertise: A proven track record of selling complex SaaS/PaaS solutions. Experience in DevOps, Infrastructure, Data, Observability, or Cybersecurity is highly preferred.

• Startup Experience: You have been at an early-stage organization where you control your own desk. You function autonomously and strive towards building something great.

• Partnership Experience: Successful track record of building equitable relationships with new partners.

We are a venture-backed tech startup and the company pioneering Kubernetes virtualization for the AI era. We raised +$30M from top-tier VCs such as Khosla Ventures (first investor in OpenAI, GitLab, Stripe, Doordash) and are in a hyper-growth phase looking for motivated people to complement our team. Our headquarters are in San Francisco (Salesforce Tower), but our team is distributed around the globe and we have a remote-first work culture.

We are the leading platform for operating GPU infrastructure, enabling AI Cloud providers to deliver a hyperscaler-like experience to their customers and AI factories that need to build that same experience for their internal teams. Our platform delivers the full operational stack operators need to run their GPU data centers — managed Kubernetes, fast isolated tenant provisioning, and automated node provisioning and lifecycle management — enabling them to accelerate time to value, reduce operational burden, and maximize the ROI of every GPU.

We're the company behind vCluster, an open-source technology for virtualizing Kubernetes (10k+ GitHub stars, 40M+ virtual clusters created since 2021). Open source is part of our DNA. At KubeCon North America 2025, we launched our Infrastructure Tenancy Platform for AI — a Kubernetes-native framework purpose-built for running AI, ML, and GPU-intensive workloads anywhere, with an NVIDIA-validated reference architecture for DGX systems.

Benefits

We offer the following benefits:

• Competitive Salary: We offer a competitive compensation package, including equity.

• Platinum-Level Insurance: Health, dental, vision, and life Insurance, including plans for you and eligible dependents (benefits vary depending on country).

• Flexible Working Schedule:  You have a doctor’s appointment or need to head to the supermarket to get groceries at 2pm? We won’t have an issue with that. To us, results matter more than clocking in and out at the same time every day.

• Workplace Flexibility:  We’re very flexible about where you work. We know things can change in life and we’re happy to adjust the work environment for you along the way.

At vCluster Labs, we value and stand for:

1. Make it Happen: We have a relentless bias for action and the grit to push through obstacles. We do whatever it takes to figure it out, put in the work, and ruthlessly prioritize the actions that drive measurable impact for the business.

2. Own the Outcome: We understand that our responsibility doesn't end when a task is checked off; it ends when the value is delivered. We connect our daily individual actions to the broader success of the company and our customers.

3. Create Wow: We measure success by the experience we generate, both inside and outside the company. For our customers, this means impressive speed and intuitive experiences. For our team, this means going the extra mile to support one another and to continuously drive each other to new heights.

4. Open Source, Open Mind: We are actively contributing to and maintaining open-source projects. Internally, we foster meritocracy — the strongest ideas win, no matter who or where they come from.

5. Build Tomorrow’s Standards, Intentionally: We don't just ship software; we define the state-of-the-art of tomorrow. We are fearless in tearing down old approaches to build something better, but we are disciplined in how we do it because we know our users rely on our technology to run mission-critical infrastructure platforms.

Compensation Range: $280K - $330K