Sales Operations & Automation Lead

Gray Swan; Pittsburgh (Allegheny County); On-site; USD 137,000 - 163,000; Full time

Benefits offered by this job

401k matching

28 days annual leave

Health, dental, and vision coverage

Catered lunches (Pittsburgh office)

Flexible work arrangements

Visa sponsorship available

Job summary

Gray Swan is building an agile Sales Operations function to scale our sales organization. This role focuses on creating structured processes across the full lifecycle—from pre-sales to contracting, delivery, invoicing, and commissions.

The ideal candidate thrives in a fast-paced, cross-functional environment and excels at turning ambiguity into well-defined workflows using automation tools and CRM systems.

Qualifications

• Strong project manager capable of handling ambiguous problems and delivering results.
• Experience designing scalable workflows and using automation tools (Zapier, n8n).
• Hands-on experience with sales processes from pre-sales to invoicing and commissions.
• Familiarity with CRM systems and reporting; able to automate and improve processes.
• Ability to work cross-functionally with Sales, Legal, Compliance, Finance, and Accounting.

Responsibilities

• Build and improve scalable systems and processes across the sales lifecycle.
• Own the deal desk operations: contracts, SOWs, security questionnaires, vendor onboarding, RFPs.
• Coordinate with internal teams to engage stakeholders at the right times.
• Manage the sales invoicing process and execute commission plans for quota-bearing members.
• Improve CRM, reporting, workflows, and automations; reduce manual work.
• Lead cross-functional projects and create playbooks and processes for scalability.

Skills

Project management

Workflow design

Cross-functional collaboration

Process improvement

Sales operations knowledge

Tools

HubSpot

Zapier

n8n

Job description

Gray Swan is building an agile Sales Operations function to scale our sales organization. This role focuses on creating structured processes across the full lifecycle—from pre-sales to contracting, delivery, invoicing, and commissions.

The ideal candidate thrives in a fast-paced, cross-functional environment and excels at turning ambiguity into well-defined workflows using automation tools and CRM systems.