Senior Deal Desk Analyst

About the role

Cornerstone is hiring a Senior Deal Desk Analyst in Costa Rica, a hybrid position reporting to the Deal Desk Manager. The role supports the company's most complex, high-value and non-standard transactions by partnering with Sales, Finance, Legal, Revenue Operations and executives to structure deals that balance customer needs, revenue goals, operational feasibility and risk. It drives commercial governance, pricing and discount reviews, non-standard terms analysis and exception management.

Key responsibilities

• Lead end-to-end review of complex, strategic and non-standard transactions across multiple sales motions
• Partner with Sales on deal structuring, commercial packaging, pricing strategies and negotiation support
• Evaluate discounts, business terms, contract structures and financial implications against company policy and margin objectives
• Coordinate cross-functional reviews with Legal, Finance, Revenue Recognition, Product, Services and executives
• Assess risk of non-standard terms, billing arrangements, product usage rights, renewals, amendments and commercial exceptions, and recommend guided approvals for exceptions needing executive review
• Support revenue recognition and billing feasibility reviews
• Analyze transactional and pipeline trends to improve forecasting accuracy
• Drive process improvements, governance initiatives and best practices, and assist with transactional support, CPQ guidance and operational tasks during peak periods

Required profile

• 3-5 years of experience in Deal Desk, Sales Operations, Revenue Operations, Sales Support, Order Management or a similar commercial operations role
• Strong understanding of sales transaction workflows, pricing approvals, quoting processes and operational controls
• Understanding of enterprise non-standard negotiations
• Ability to explain the reasoning behind policies and procedures, and to communicate clearly with executive leadership
• Experience in a fast-paced SaaS environment preferred
• Proficiency in English

Required skills

• Hands-on experience with Salesforce CRM; CPQ experience preferred
• Experience with Tackle.io and cloud marketplaces (Azure, AWS, GCP) preferred