Sales Operations & Process Automation Lead

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

Benefits offered by this job

401k match

Leave & holidays (28 days)

Health, dental, and vision coverage

Catered lunches (Pittsburgh office)

Flexible work arrangements

Visa sponsorship available

Job summary

Gray Swan is a Pittsburgh-based AI safety company seeking a Sales Operations Lead to build scalable systems across the sales lifecycle, from pre-sales through invoicing and commissions. You’ll own the deal desk, coordinate contracts and SOWs, manage vendor onboarding and RFPs, and partner across Sales, Legal, Compliance, Finance, and Accounting to keep processes efficient.

You’ll optimize CRM workflows in HubSpot, drive automation, and create playbooks that scale with the company, offering a

Qualifications

• Strong project management to structure ambiguous problems and drive to completion.
• Experience with workflows and flow charts to build automations.
• Hands-on experience with CRM systems and reporting; automate where possible.
• 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, coordinating contracts, SOWs, security questionnaires, vendor onboarding, and RFPs.
• Partner with Sales, Legal, Compliance, Finance, and Accounting to ensure timely engagement of stakeholders—full lifecycle transparency.
• 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 reducing manual work.
• Lead cross-functional projects and create playbooks, documentation, and scalable processes.

Skills

Project management

Workflow design

CRM systems

Automation

Cross-functional collaboration

Problem solving

Attention to detail

Sales knowledge

Tools

HubSpot

Zapier

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Job description

Gray Swan is a Pittsburgh-based AI safety company seeking a Sales Operations Lead to build scalable systems across the sales lifecycle, from pre-sales through invoicing and commissions. You’ll own the deal desk, coordinate contracts and SOWs, manage vendor onboarding and RFPs, and partner across Sales, Legal, Compliance, Finance, and Accounting to keep processes efficient.

You’ll optimize CRM workflows in HubSpot, drive automation, and create playbooks that scale with the company, offering a