Head of Deal Desk

JOB SUMMARY

We are seeking an experienced Head of Deal Desk to establish and lead iTradenetwork's first Deal Desk function. This high-impact role reports to the CFO with a dotted line to the CRO, positioning you at the critical intersection of Finance and Sales. You will build scalable commercial processes from the ground up, enabling efficient and profitable deal execution while supporting our aggressive growth targets in the food supply chain SaaS market.

The ideal candidate brings 6+ years of Deal Desk/Sales Operations leadership experience, deep FP&A expertise, and a proven track record of building world-class commercial operations in high-growth SaaS environments. You will own the development of ROI and value realization models to strengthen our enterprise sales motion and align pricing with customer outcomes. This role will also own the development of ROI and value realization models to support sales in articulating the customer business case, strengthening deal justification, and aligning pricing with expected outcomes.

Key Responsibilities:

Deal Desk Foundation & Operations

• Build iTradenetwork's Deal Desk function from scratch - establish processes, approval workflows, playbooks, SLAs, and governance frameworks.
• Serve as primary advisor on complex deal structuring for all sales opportunities, with focus on larger enterprise deals 
• Partner with Sales to balance deal velocity with margin protection and ASC 606 compliance
• Own the approval matrix for discounting, non-standard terms, bundling, and professional services attachments
• Develop a set of packaged offerings for Support, Services and Implementation that enable contractually recurring bookings co-termed with the overall renewal.
• Work with Business Development to help streamline and rationalize contracts for referral, technology and services partners.
• Reduce deal cycle times while maintaining pricing discipline aligned with our basis points pricing model
• Perform commission calculations and assignment ensuring accurate and timely compensation processing

Pricing Strategy & Value Engineering

• Maintain ROI/value realization models specific to food industry use cases.
• Establish a structured, role- and level-based pricing discount authorization model.
• Create customer-facing business case frameworks quantifying benefits across our product portfolio 
• Design pricing calculators and commercial templates for different customer segments (distributors, retailers, growers/shippers, manufacturers)

Systems & Process Excellence

• Lead Salesforce CPQ optimization, Streamlining the quote-to-cash process 
• Integrate Deal Desk workflows with FP&A/Accounting systems
• Build scalable processes to support $115M+ ARR business growing toward strategic targets
• Oversee commission calculation processes and ensure integration with payroll and finance systems

Analytics & Executive Reporting

• Deliver insights on deal velocity, win rates, discounting trends, and margin impact
• Create executive dashboards for ELT visibility including CRO and leadership team
• Analyze GRR/NRR trends and renewal performance across customer segments
• Track professional services attachment rates and implementation success metrics
• Provide commission attainment reporting and forecasting

Cross-Functional Leadership

• Partner closely with Sales, Finance, Legal, and Customer Success on late-stage deal execution
• Collaborate with Sales Operations on territory planning and commission plan design
• Train Sales teams on pricing best practices, ROI storytelling, and approval processes
• Ensure accurate commission assignments and resolve disputes in collaboration with Sales leadership

What you’ll need:

• 6–8 years of progressive experience in FP&A, Pricing Strategy, or Deal Desk roles within B2B SaaS.
• Proven success owning or building out a deal desk function in a fast-paced growth company.
• Strong command of SaaS business models, ARR/NRR/GRR, gross margin, and general revenue recognition principles (ASC 606).
• Experience developing customer-facing ROI models, value calculators, or business case frameworks.
• Excellent Excel / modeling skills and ability to translate analysis into action.
• Comfortable influencing executives and managing cross-functional projects.
• Highly collaborative, detail-oriented, and resourceful self-starter.

Nice-to-Have Qualifications:

• Familiarity with tools such as Salesforce, CPQ, DocuSign, and CLM systems is a plus.

If you are a highly motivated and results-driven individual, with a passion for driving growth in a fast-paced, entrepreneurial environment,  we encourage you to apply for this exciting opportunity. We offer a competitive salary, comprehensive benefits package, and a dynamic work culture that values collaboration, innovation, and personal development.