Sales Operations Associate

About Gray Swan

Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for enterprise teams deploying AI.

We're a team of approximately 50 people, well-funded and growing quickly. Our work directly influences how the world deploys AI agents and systems at scale.

Learn more about how we work.

The Role

We’re looking for a Sales Operations Associate to build the systems, processes, and operational infrastructure that enable our sales organization to scale. This is a highly cross-functional, back-office role for someone who loves creating structure, solving operational problems, and making teams more efficient. You’ll work closely with Sales, Legal, Compliance, Finance, and Accounting to improve processes across the full sales lifecycle—from pre-sales and contracting through delivery, invoicing, and commissions. This role also has the opportunity to evolve as the company grows, with the possibility to take on additional Sales and Revenue Operations initiatives.

What You’ll Do:

• Build and improve scalable systems and processes across the sales lifecycle, including pre-sales, contracting, post-sales, project/deliverable tracking, and internal handoffs.

• Own the operational side of our deal desk, coordinating contracts, SOWs, security questionnaires, vendor onboarding, RFPs, and other deal-related requirements with the appropriate internal teams.

• Partner with Sales, Legal, Compliance, Finance, and Accounting to ensure the right stakeholders are engaged at the right time and that processes move efficiently.

• Manage the sales-side invoice process and execute commission plans for quota-carrying team members.

• Manage and optimize our CRM (HubSpot), reporting, workflows, and automations while continuously looking for opportunities to eliminate manual work.

• Lead cross-functional projects and create playbooks, documentation, and processes that bring greater structure and scalability to the organization.

Who You Are:

• You’re a strong project manager who can take an ambiguous problem, create structure, coordinate stakeholders, and drive it through to completion.

• You think in terms of workflows and flow charts, and have used tools like Zapier, n8n, etc. to build automations based on these.

• You’re highly organized and detail-oriented, with strong judgment around what you can solve independently and when to pull in Legal, Finance, Compliance, or other teams.

• You have hands-on experience working with sales teams and deal cycles.

• You’re a process-minded problem solver who naturally asks, “How can we make this easier, more efficient, and more scalable?”

• You’re comfortable working across multiple functions and managing several priorities at once in a fast-moving environment.

• You have experience with CRM systems and reporting, and you’re comfortable learning and improving systems rather than simply maintaining them.

• You’re a hands-on generalist who isn’t afraid to jump into the details, execute manually when necessary, and then find a way to automate it.

Bonus Points If You Have:

• Experience with HubSpot or another CRM, including workflows, reporting, data management, and automation.

• Experience in Sales Operations, Revenue Operations, Deal Desk, Business Operations, Sales, or a similar cross-functional role.

• Experience working with Sales, Legal, Compliance, Finance, or Accounting on contracts, security requirements, vendor onboarding, or related processes.

• Experience building contracting processes, deal desk workflows, playbooks, or other operational frameworks from the ground up.

• Experience supporting commission administration, RFPs, security questionnaires, or sales-side invoicing processes.

• Experience identifying opportunities for automation and using technology to streamline repetitive operational work.

If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.

You’ll Thrive Here If You:

• You genuinely enjoy problem solving and get satisfaction from making the organization run better behind the scenes.

• You’re energized by creating structure where there isn’t much structure yet, and you’re comfortable figuring things out as you go.

• You’re naturally curious and enjoy learning how different parts of a business work together.

• You have a strong sense of ownership and don’t wait to be told exactly what to do when you see something that needs fixing.

• You’re a generalist at heart—you like having your hands in a variety of projects rather than being narrowly focused on one system or function.

• You want a role that can grow with the company and are excited by the opportunity to shape what Sales Operations looks like as we scale.

What We Offer:

We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.

Compensation: $136,500 - $163,000 plus performance based bonus and meaningful equity package

Benefits:

• 401k with up to 4% matching

• 28 days annual leave (vacation + holidays)

• Health, dental, and vision coverage

• Catered lunches (Pittsburgh office)

• Flexible work arrangements

• Visa sponsorship available for exceptional candidates

Typical Interview Process

🔎 Application review. We read everything; we’ll respond within 10 days.

🗣 Recruiter Screen. We learn about you; you learn about us.

🧑‍💻 Technical interview or Hiring Manager Interview.

💻 Role related assessment

🗣 Experience & culture interview

😇 Reference checks. We’ll reach out to 3 references that you provide.

📃 Offer. If it’s mutual, we move fast.

How to Apply

Submit your resume, link to your portfolio, and answer the questions on the application.