Senior Deal Desk Analyst - Costa Rica

We're looking for a Senior Deal Desk Analyst - Costa Rica. This role is Hybrid, Costa Rica.

Role Overview

As a Senior Deal Desk Analyst, you will serve as a trusted commercial advisor supporting the company's most complex, high-value, and non-standard transactions. While providing guidance across core Deal Desk processes, the primary focus of this role is partnering with Sales, Finance, Legal, Revenue Operations, and executive stakeholders to structure strategic deals that balance customer requirements, revenue objectives, operational feasibility, and risk management. The role is responsible for driving commercial governance, deal strategy, pricing and discount reviews, non-standard terms analysis, and exception management to accelerate deal closure while protecting company interests.

Primary Responsibilities

• Lead end-to-end review and support 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 to ensure compliance with company policies and margin objectives.
• Coordinate cross-functional reviews with Legal, Finance, Revenue Recognition, Product, Services, and executive stakeholders.
• Assess risk associated with non-standard terms, billing arrangements, product usage rights, renewal structures, amendments, and commercial exceptions.
• Provide recommendations and guided approvals for exceptions requiring executive review.
• Support revenue recognition and billing feasibility reviews to ensure proposed deal structures can be operationalized.
• Analyze transactional and pipeline trends to improve forecasting accuracy and commercial decision-making.
• Drive process improvements, governance initiatives, and best practices that improve scalability and reduce commercial risk.
• Assist with transactional support, CPQ guidance, and operational activities during peak periods, with strategic deal support remaining the primary responsibility.

Key Focus Areas

• Strategic Deal Structuring
• Pricing and Discount Governance
• Commercial Packaging and Negotiation Support
• Commercial Risk Assessment
• Non-Standard Contract Terms and Legal Coordination
• Executive Exception Reviews and Approvals
• Revenue Recognition and Billing Feasibility
• Forecasting, Analytics, and Deal Insights

You've got what it takes if you have...

• 3-5 years of experience in Deal Desk, Sales Operations, Revenue Operations, Sales Support, Order Management, or a similar commercial operations role.
• Hands-on experience with Salesforce CRM; CPQ experience preferred.
• Experience working with Tackle.io and Cloud Marketplaces (Azure, AWS, GCP) preferred.
• Strong understanding of sales transaction workflows, pricing approvals, quoting processes, and operational controls.
• Understanding Enterprise non-standard negotiations.
• Ability to clearly articulate the reasoning and business objectives behind organizational policies, procedures, and internal guidelines.
• Ability to manage multiple priorities while maintaining attention to detail and accuracy.
• Strong analytical, problem-solving, and organizational skills.
• Excellent written and verbal communication skills, with the ability to effectively engage and influence executive leadership and senior stakeholders through clear, confident, and professional communication.
• Experience working in a fast-paced SaaS environment preferred.
• Demonstrated commitment to process improvement and operational excellence.
• Consideration for privacy, security, and compliance obligations.
• Proficient in the English language.
• Thrives in a fast-paced environment and understands the critical importance of meeting EOQ and EOY deadlines, balancing speed, accuracy, and compliance to support successful deal closure.

Our Growing Presence in Costa Rica

Cornerstone is excited to be building a new hub in Costa Rica as part of our continued investment in growing our global talent and capabilities. We are bringing together teams across a variety of functions, creating exciting opportunities for people to join us at the ground floor of this new chapter and help shape how we grow in the region.

We have invested in a new office in Costa Rica, with construction beginning soon, and we expect our presence and capabilities in the region to continue expanding over time. For those joining us now, this is a unique opportunity to help build something from the beginning, work alongside talented colleagues across Cornerstone globally, and be part of our longer-term growth in Costa Rica.

Employment Structure

As we establish our operations in Costa Rica and complete the process to operate under the country’s Free Trade Zone Regime, Cornerstone is partnering with Recluta, our local Employer of Record (EOR).

Our Culture

Spark Greatness. Shatter Boundaries. Share Success. Are you ready? Because here, right now – is where the future of work is happening. Where curious disruptors and change innovators like you are helping communities and customers enable everyone – anywhere – to learn, grow and advance. To be better tomorrow than they are today.

Who We Are:

At Cornerstone, we believe in AI that works in the service of people, amplifying their judgment to drive high-performing, future-ready organizations forward. Cornerstone Workforce AI™, the intelligence platform for workforce readiness, brings together workforce and labor market data into a proprietary Cornerstone People Graph™, translating signals into intelligence, targeting learning where it matters, developing critical skills, and surfacing hidden talent. Delivered as an open, enterprise platform across whatever application your people work in every day, Cornerstone Workforce AI is built for scale, security, and trust, with certified AI guardrails. As an industry leader, Cornerstone is helping approximately 7,000 organizations, 140M+ users, across 186 countries build continuous workforce readiness.

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