About this Deal Desk Lead role at Yoodli AI Roleplays
Careers at Yoodli
We're on a mission to help people communicate with confidence
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.
Why Yoodli
- Competitive compensation ($155,000 - $170,000) + meaningful equity
- Full benefits: healthcare, dental, vision, 401k, flexible PTO
- High-impact, mission-driven work with direct customer feedback loops
- Work with a humble, driven, deeply collaborative team
- A product you’ll use and believe in – every single week
