Deal Desk Lead

Yoodli AI Roleplays; Seattle (WA); Hybrid; USD 120,000 - 180,000; Full time

Job summary

Yoodli is seeking a Deal Desk Lead to own the end-to-end deal process in a hybrid Seattle-based role. You will partner with Revenue Ops, Legal, Finance, and Sales to enforce policies, document workflows, and improve deal velocity.

You will drive pricing governance, advise on non-standard terms, manage contract handoffs, and ensure data integrity in CRM. This is a high-impact, cross-functional role.

Qualifications

• 5-7 years of deal desk experience in SaaS or startup environments.
• Understanding of GAAP principles and basic accounting processes.
• Experience with CRM, CPQ tools, and Hubspot is a plus.
• Experience with quote-to-cash systems and strong attention to detail.

Responsibilities

• Own the Quote-to-Cash lifecycle, ensuring a smooth workflow from quote to invoicing.
• Develop and manage pricing governance to balance velocity with accuracy.
• Advise Sales on non-standard terms and multi-year contract implications.
• Streamline contract handoffs and ensure compliant, timely approvals.
• Maintain data quality in CRM to support forecasting and revenue recognition.
• Create clear deal policies to accelerate velocity and reduce friction.
• Oversee order fulfillment and verify license terms and duration.
• Provide business insights from deal desk metrics to improve pricing.
• Lead continuous improvement of deal desk processes and playbooks.

Skills

Deal desk experience

Cross-functional collaboration

Attention to detail

Communication skills

Bias toward action

Education

GAAP principles understanding

Tools

CRM

CPQ

Hubspot

Job description

Yoodli is an AI-powered experiential learning platform that uses AI roleplays to personalize real-life practice and transform how organizations learn and prepare. We're pioneering a new category — AI Roleplays — because we believe nobody should miss out on the opportunities they deserve because of how they communicate. Static content doesn't create behavior change. Practice does.

We've raised $60M — including a $40M Series B led by WestBridge Capital — backed by Madrona, Neotribe, Cercano, and incubated at the Allen Institute for AI. Our customers include Google Cloud, Snowflake, Databricks, RingCentral, SAP, FranklinCovey, KornFerry, Sandler Training, Toastmasters, and many more — with learners in over 150 countries. We're headquartered in the heart of Seattle, and we're having a lot of fun along the way. We value humility, a bias for action, and the belief that we win together. Try the platform free at yoodli.ai.

The Role

As Deal Desk Lead, you will be the operational center of gravity for Yoodli’s customer deal flow. This is more than just a sales operations role: you will own the process, with the authority to enforce rules and use your judgment to decide when exceptions are warranted. You will partner with Sales, Revenue Operations, Legal and Finance, ensuring the cross functional processes that have meaningful business impact are designed, documented and adhered to.

This is a Hybrid role: 3 days in-office at our Seattle HQ (lunch included) + 2 days remote.

What You'll Do:

• Own the Quote-to-Cash Lifecycle: Partnering with RevOps, architect and oversee the end-to-end deal workflow, optimizing the steps from initial quote generation to invoicing. You’ll serve as the process owner, ensuring consistency and efficiency across every customer engagement.
• Drive Pricing Governance: Develop and manage a sales approval matrix and approval process that balances sales velocity with revenue integrity.
• Provide Commercial Guidance: Act as the strategic partner to Sales to support sales that require non-standard terms. You’ll advise on multi-year contracts, renewal mechanics and contractual provisions, calling out downstream implications.
• Optimize Legal & Contract Handoffs: ensure sales reps are trained to follow our standard legal processes and understand how to document legal requests.You will streamline the review process, manage contract workflows, and ensure all deal documentation is accurate and compliant, preventing bottlenecks that stall deal closure.
• Ensure Data Integrity & CRM Hygiene: Champion high-quality data standards within our CRM. You will partner with Revenue Operations to ensure data is captured and validated, ensuring that forecasting, revenue recognition, and renewal management are built on a solid foundation of accurate data.
• Standardize Policies & Drive Velocity: Develop and enforce clear deal policies that turn ad-hoc processes into scalable revenue operations. You will analyze cycle times to eliminate friction, providing the team with the playbooks needed to accelerate deal velocity and optimize manual processes with automation.
• Own order fulfillment: you will ensure all contracts pass approval before signatures added and you will own license fulfillment, ensuring features and duration are correct.
• Actionable Business Intelligence: Serve as the source of truth for deal desk metrics. You will analyze discounting trends, customer profitability, and operational KPIs to deliver actionable insights that drive smarter pricing decisions and higher win rates.
• Continuous Improvement Analysis: Own the continuous improvement of the deal desk function. Systematically log operational errors, analyze patterns to uncover root causes, and evolve our policies and playbooks to close gaps and ensure long-term scalability.

You Might Be a Fit If You...

• Have 5-7 years of deal desk experience, preferably in a SaaS or startup environment.
• Understand core GAAP principles and basic accounting processes.
• Expertise with CRM, CPQ and related sales process tools. Experience with Hubspot is a plus.
• Experience with quote to cash systems and are highly organized with strong attention to detail and a bias toward action.
• Communicate clearly and work comfortably with cross-functional partners.
• Are excited to roll up your sleeves in a fast-paced, evolving environment and take ownership of your work.