Deal Desk Director

Why CAST AI?

CAST AI is the leading Kubernetes cost optimization platform for AWS, GCP and Azure customers. The company is on a mission to deliver a fully automated Kubernetes experience. What’s unique about CAST AI is that its platform goes beyond monitoring clusters and making recommendations; it utilizes advanced machine learning algorithms to analyze and automatically optimize clusters, saving customers 50% or more on their cloud spend, improving performance and reliability, and boosting DevOps and engineering productivity.

The company has raised $73M from investors, including Cota Capital, Creandum, Uncorrelated Ventures, and Vintage Investment Partners. CAST AI has nearly 200 employees globally and is headquartered in Miami, Florida.

However, this is merely the beginning. Our product roadmap is filled with exciting innovations that are yet to come. We are searching for intelligent, motivated, and self-reliant people to help us fulfill this ambitious mission.

Core values that hold us all together:

PRACTICE CUSTOMER OBSESSION. Focus on the customer journey and work backwards. Strive to deliver customer value and continuously solve customer problems. Listen to customer feedback, act, and iterate to improve customer experience.

LEAD. Take ownership and lead through action. Think and act on behalf of the entire company to build long-term value across team boundaries.

DEVELOP AND HIRE THE BEST. Strive to raise the performance bar by continuously investing in yourself, the team and by hiring the best possible candidates for every position. Drive towards personal development and professional growth, and mentor others to raise the collective bar.

EXPECT AND ADVOCATE CHANGE. Strive to innovate and accept the inevitable change that comes with innovation. Constantly welcome new ideas and opinions. Share insights responsibly with unwavering openness, honesty, and respect. Once a path is chosen, be ready to disagree and commit to a direction.

Role overview

We’re looking for a sharp, strategic, and collaborative Deal Desk Director to support our growing Sales and Customer Success team and optimize how we structure deals.

This role sits at the intersection of Sales, Customer Success, Finance, Legal, and RevOps - ensuring deals are not only competitive and customer-friendly, but also financially sound and scalable.

You’ll play a key role in shaping our pricing strategy, streamlining deal workflows, and driving revenue growth through smart deal-making.

Responsibilities

• Deal Structuring: Support sales and customer success teams by helping structure complex deals, including custom pricing, discounts, payment terms, and bundling
• Pricing Strategy: Ensure pricing aligns with the company's revenue goals, margin targets, and market standards. Help evolve our pricing models, discount guidelines, and approval workflows in line with business goals.
• Approval Workflows: Oversee and manage deal approval workflows, ensuring necessary stakeholders (Sales, Customer Success, Finance, Legal, Product, and Leadership) review and sign off as needed
• Policy Enforcement: Maintain and enforce pricing and discounting policies to ensure consistency and reduce risk
• Analytics & Reporting: Work with RevOps team to provide insights into deal performance, win/loss rates, and discount trends; make recommendations for policy or strategy adjustments.

Requirements

• 7-10 years of experience in deal desk / pricing strategy, preferably in a SaaS or recurring revenue business. 
• Degree in finance, business, and/or economics
• Clear communicator and trusted partner - you can influence decisions while keeping sales velocity high
• Experience in sales operations, finance, pricing strategy, or revenue operations
• Strong knowledge of SaaS pricing models, revenue recognition principles, and enterprise sales cycles
• Proven ability to work cross-functionally and manage multiple stakeholders in a fast-paced environment
• Strong analytical and modeling skills. Strong attention to detail, spot risks, opportunities, and anomalies in deal structures
• International experience and a global mindset; comfortable navigating pricing strategies, stakeholders, and deal dynamics across regions

What's in it for you?

• A chance to shape the deal desk function from the ground up at a high-growth SaaS company.
• High-impact role with visibility across executive leadership, Sales, and Finance. Reports to the CFO.
• Competitive salary, great benefits, and a remote-friendly culture built on trust and transparency. 
• Enjoy a flexible, remote-first global environment.
• 401(k) retirement plan 100% company match on employee contributions up to 6% of pay (available after 3 months of employment).
• Access UnitedHealthcare plans including medical, dental, and vision coverage.
• Equity options.
• Collaborative, motivated team that values both precision and creativity.