Job description
Restaurant365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides a unique, centralized solution for accounting and back-office operations for restaurants. Restaurant365’s culture is focused on empowering team members to produce top-notch results while elevating their skills. We’re constantly evolving and improving to make sure we are and always will be “Best in Class” … and we want that for you too!
The Director of Deal Strategy & Management will lead the transformation and modernization of our Deal Strategy and Deal Desk Management operations, with a strong focus on driving efficiency through automation, AI, and scalable processes. Supporting quote-to-cash activity, this role will partner cross-functionally to streamline approvals, implement intelligent automation, and bring next-level operational rigor to pricing and deal execution. We’re looking for a highly collaborative, forward-thinking leader who thrives in a fast-paced environment and knows how modern Deal Desks should operate at scale.
How you’ll add value:
- 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
What you’ll need to be successful in this role:
- 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
- Experience with tools such as AI transcription, DocGen, Gong, and workflow automation platforms
- Bachelor’s degree in Business, Finance, Operations, or related field preferred
R365 Team Member Benefits & Compensation
- This position has a salary range of $144,730 - $217,000. The above range represents the expected salary range for this position. The actual salary may vary based upon several factors, including, but not limited to, relevant skills/experience, time in the role, business line, and geographic location. Restaurant365 focuses on equitable pay for our team and aims for transparency with our pay practices.
- Comprehensive medical benefits, 100% paid for employee
- 401k + matching
- Equity Option Grant
- Unlimited PTO + Company holidays
- Wellness initiatives
#BI-Remote
$144,730 - $217,000 a year
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DYN365, Inc d/b/a Restaurant365 is an equal opportunity employer.
