Sales Operations Associate

Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for leading frontier labs and build real‑time threat detection and adaptive adversarial red‑teaming agents for enterprise teams deploying AI. Our team of ~50 people is well‑funded, growing quickly, and directly influences how AI agents and systems are deployed at scale.

About 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 highly cross‑functional, back‑office role focuses on creating structure, solving operational problems, and making teams more efficient. You’ll partner with Sales, Legal, Compliance, Finance, and Accounting across the full sales lifecycle—from pre‑sales and contracting through delivery, invoicing, and commissions.

Responsibilities

• 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 the 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.

Requirements

• Strong project‑management skills: ability to take ambiguous problems, create structure, coordinate stakeholders, and drive to completion.
• Experience thinking in workflows and flowcharts; familiarity with automation tools such as Zapier, n8n, etc.
• Highly organized, detail‑oriented, with sound judgment about when to act independently versus involving Legal, Finance, or Compliance.
• Hands‑on experience working with sales teams and deal cycles.
• Process‑minded problem solver who constantly asks how to make operations easier, more efficient, and more scalable.
• Comfortable working across multiple functions and managing several priorities in a fast‑moving environment.
• Experience with CRM systems and reporting; eager to learn and improve systems rather than merely maintain them.
• Hands‑on generalist attitude: willing to execute manually when needed and then automate the solution.

Bonus Points

• Experience with HubSpot or another CRM, including workflows, reporting, data management, and automation.
• Background in Sales Operations, Revenue Operations, Deal Desk, Business Operations, Sales, or a similar cross‑functional role.
• Experience collaborating 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.
• Proven ability to identify automation opportunities and use technology to streamline repetitive operational work.

Pay

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

Benefits

• 401(k) 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

Interview Process

• Application review (response within 10 days)
• Recruiter screen
• Technical interview or hiring manager interview
• Role‑related assessment
• Experience & culture interview
• Reference checks (up to 3 references)
• Offer – fast decision if mutual interest