Director, Deal Strategy & Management

Summary

Join Restaurant365, a SaaS company revolutionizing the restaurant industry, as the Director of Deal Strategy & Management. Lead the transformation of Deal Strategy and Deal Desk Management operations, focusing on efficiency through automation, AI, and scalable processes. Support quote-to-cash activities by partnering cross-functionally to streamline approvals and implement intelligent automation. This role requires a highly collaborative leader who thrives in fast-paced environments and understands modern Deal Desk operations at scale. You will own and lead the Deal Desk function, architect scalable workflows, design automated processes, collaborate cross-functionally, guide pricing and packaging, maintain deal playbooks, drive continuous process improvement, build enablement content, own reporting and analytics, and partner with other teams for seamless reporting. The position offers a competitive salary and comprehensive benefits.

Requirements

• 10+ years of experience leading or scaling a SaaS Deal Desk or Revenue Operations function
• Deep expertise in quote-to-cash processes, CPQ, Salesforce, and deal workflow optimization
• Proven success driving automation-first initiatives and integrating AI into operational workflows
• Strong analytical mindset with the ability to translate data into action
• Excellent communication and collaboration skills across sales, legal, product, and finance stakeholders
• Passion for simplifying complex processes through modern tools and design thinking

Responsibilities

• Own and lead the Deal Desk function, supporting quote-to-cash for 500+ deals/month
• Architect and execute scalable workflows through AI tools, automation, and system-driven approvals
• Design and implement automated deal validation and approval processes using Salesforce, CPQ, and other tools
• Collaborate cross-functionally with Legal, Finance, Sales, and Product to structure and optimize deals
• Guide pricing and packaging execution, with built-in controls and automation
• Maintain deal playbooks, policies, and approval frameworks — embedding automation and AI-enhanced workflows
• Drive continuous process improvement with technologies such as AI transcription, document automation, and smart routing
• Build enablement content and self-service quoting tools to improve speed and reduce manual effort
• Own reporting and analytics for Deal Desk — including cycle times, exception rates, and automation impact
• Deliver insights that shape revenue strategy, pricing governance, and pipeline performance
• Partner with Commissions and Accounting to ensure seamless downstream reporting and reconciliation

Preferred Qualifications

• Experience with tools such as AI transcription, DocGen, Gong, and workflow automation platforms
• Bachelor's degree in Business, Finance, Operations, or related field preferred

Benefits

• Comprehensive medical benefits, 100% paid for employee
• 401k + matching
• Equity Option Grant
• Unlimited PTO + Company holidays
• Wellness initiatives