Director, Deal Strategy & Management
Remote
Sales – Deal Desk /
Full Time /
Remote
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
#LI-JZ1
DYN365, Inc d/b/a Restaurant365 is an equal opportunity employer.
