Deal Desk Lead

Yoodli helps people get measurably better in their careers. We help individuals achieve this by helping them land their job, onboard at their companies, learn new skills, practice a speech, sales pitch or difficult conversation, and then take your Yoodli coach with you from one role to the next. For organizations, this means helping you upskill your entire workforce for the AI Future.
We’ve always believed in the human potential. In 2021, Esha and Varun started Yoodli as an AI communication coach - to help people communicate with confidence. Since then, our users have used Yoodli for so much more: to learn new concepts through AI Roleplays, practice different kinds of conversations (sales pitches, job interviews, manager conversations), and even use Yoodli as their personal coach to help them learn to use Gemini, Claude or other AI Tools. It’s why we expanded our technology to be the AI Platform for Human Skills.
Who We Are
Our team includes former employees from Google, Apple, Microsoft, Tableau, and beyond, united by a passion for empowering people using AI. We're headquartered in the heart of Seattle, and we're having a lot of fun along the way. Our culture is built on failing fast, iterating constantly, and taking bold bets. We value humility, authenticity, and a can-do-attitude. 
We’re backed by Madrona, Neotribe the Allen Institute for AI, Cercano, and have raised over $60M to date.
Our customers include Google, RingCentral, Databricks, Snowflake, Sandler Sales, Dale Carnegie, Toastmasters, and users in over 150 countries. We’ve been featured in Forbes, Fortune, WSJ, Geekwire, ZDNet, and several other outlets (www.yoodli.ai/press). You can try the platform for free at www.yoodli.ai and learn more about us in this TED Talk.

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.

• 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.

• 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