We're looking for a

Deal Desk Manager

This role is Hybrid, Costa Rica

The Deal Desk Manager will report to the Deal Desk Director and manage a team of Senior Analysts supporting Cornerstone's Global Sales organization. This role serves as a primary point of contact for the global Sales team, providing guidance on quote generation, deal structuring, pricing, policy adherence, and compliance. As a member of the broader Deal Desk organization, you will contribute to business scalability through process improvement, policy standardization, operational excellence, and cross-functional collaboration. The ideal candidate thrives in a fast-paced environment, acts with urgency, and effectively manages competing priorities and tight deadlines.

In this role you will..

• Manage the Deal Desk day to day function and assist the Sales org with Deal structuring, Quoting and Pricing, Special Terms and Exception Approvals Management
• Foster relationships with direct reports, sales leaders and their respective teams
• Develop a feedback loop with Sales and provide on-going recommendations regarding the improvement of policies and process
• Develop and lead a team of talented, smart individuals dedicated to improving/creating the greatest experience for our internal Sales, Finance, & Legal teams
• Work with the Director to continuously improve team engagement
• Continuous review of deal progression and collaboration with colleagues to ensure optimal deal cycle times
• Review Sales-proposed quotes, provide feedback and coaching to both Sales and analysts, ensure compliance with published sales and business policies, and approve or reject/escalate quotes as needed based on policy and business judgement
• Challenge legacy policies and procedures that complicate the Order to Cash process

• Participate in deal review and strategy discussions with sales teams and internal stakeholders, providing guidance on policy interpretation, deal structuring options, pricing considerations, and approval requirements.

• Manage ServiceNow incoming ticket queues and provide analysis on ticket trends
• Identify deal trends and drive efforts to categorize historical contracting and deal structuring trends based on sales segment or industry vertical

• Maintain deep knowledge of product offerings, roadmap updates, and release changes to effectively support deal structuring, pricing decisions, quoting guidance, and sales enablement.

• Manage Deal Desk approval queue, ensuring deals are reviewed timely

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

• Bachelor’s degree or equivalent experience

• 3-5 years of experience in a Deal Desk, Revenue Operations, Sales Operations, or similar commercial support function
• Previous people management experience, including coaching, developing, and leading high-performing teams
• Demonstrated ability to work with urgency, manage competing priorities, and meet tight deadlines in a fast-paced environment

• Strong Leadership Skills
• Communication needs to be clear and able to articulate (Proficient in English)
• Proficiency with Salesforce Quoting, & CPQ, Apptus CPQ and DocuSign CLM tools (ale to trouble shoot issues review resources before seeking assistance(
• Intermediate / advanced skills in MS Excel (VLOOKUP & Pivot Charts a must)
• Strong PowerPoint and Presentation Skills
• A selfless team player mentality
• An ability to be flexible and adaptable in a changing environment
• A strong aptitude to learn new things easily
• Highly organized with the ability to multi-task & handle multiple deadlines simultaneously
• Precise attention to detail
• Demonstrated commitment to valuing diversity and contributing to an inclusive working and learning environment
• Consideration for privacy and security obligations

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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