---
title: 'Deal Desk Lead at Yoodli AI Roleplays'
canonical: 'https://feeny.ai/job/deal-desk-lead-yoodli-ai-roleplays-seattle-e1dw687468st'
type: 'job'
last_seen: '2026-09-08'
---

# Deal Desk Lead at Yoodli AI Roleplays

- **Company:** Yoodli AI Roleplays
- **Location:** Seattle, WA
- **Work type:** hybrid
- **Posted:** 2026-08-14
- **Last confirmed live:** 2026-09-08
- **Apply:** https://job-boards.greenhouse.io/yoodliinc/jobs/4371012009

## Job description

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](https://www.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

## About Yoodli AI Roleplays

## Company Overview

- **One-liner**: Yoodli provides an AI-powered roleplay platform that helps individuals and enterprises practice and improve communication skills through realistic, judgment-free simulations.
- **Entity Type**: Private (Series B)
- **Headquarters**: Seattle, Washington, USA
- **Founded**: 2021
- **Founders**: Varun Puri (CEO) and Jamie Rapperport (Chief Customer Officer)

## Core Business

- **Primary industry/industries**: AI-powered communication coaching, sales enablement, enterprise learning & development
- **Target customers**: B2B (enterprise sales organizations, HR/L&D teams) and B2C (job seekers, public speakers, managers)
- **Mission or purpose statement**: "To help everyone communicate with confidence."

## Products & Services

- **AI Roleplays**: A SaaS platform where learners practice high-stakes conversations with realistic AI personas. Provides instant feedback on delivery, clarity, and pacing. Supports multi-persona and multi-participant roleplays.
- **AI Tutor**: On-demand guidance that reinforces best practices between live coaching sessions, helping learners improve without relying on manager availability.
- **Admin Analytics & Readiness**: Dashboards for tracking individual and team progress, scalable certification workflows, and objective skill development metrics.
- **Free App**: A standalone version for individual users (public speaking, interview prep) available at app.yoodli.ai.

## Market Standing

- **Valuation/Market Cap**: Not disclosed
- **Key Metric**: Total funding – $53M (including a $40M Series B round)
- **Notable Investors/Partners**: Madrona, Neotribe, Allen Institute for AI, Cercano, Emergence Capital, GGV Capital, and individual angels such as Brian Jacobs, Jeff Richards, and Kirby Winfield.
- **Growth Signals**: Customers include Google, RingCentral, Databricks, Snowflake, Sandler Sales, Dale Carnegie, and Toastmasters. Used in 150+ countries. Featured in Forbes, Fortune, WSJ, GeekWire, and a TED Talk. SOC 2 Type 2 certified and GDPR compliant. Supports 40+ languages for global deployment.

## Competitive Advantages

- **Experiential learning**: Replaces passive content (videos, slide decks) with spoken, interactive practice that leads to measurable behavior change.
- **Realistic AI personas**: Roleplays reflect real objections, buyer personas, and pressure, offering consistent and objective feedback every time.
- **Enterprise-ready**: SOC 2 Type 2 security, seamless integration with LMS/CRM tools, and scalable administration for global teams.
- **Privacy-first**: Feedback is private and user-controlled; complements live coaching rather than replacing it.

## Strategic Focus

- Scale the “AI Roleplays” category across enterprise sales, enablement, and leadership development.
- Expand adoption in healthcare, financial services, higher education, and professional services.
- Continue innovating on multi-persona, multi-language, and multi-modal roleplay experiences.
- Grow the self-serve B2C free tier to drive brand awareness and bottom-up enterprise adoption.

## Why Work Here

- **Culture**: Values include humility, authenticity, bias for action, “win together,” and bringing your whole self to work. The team is described as hardworking, creative, and inclusive.
- **Impact**: Opportunity to build and scale a company from the ground up, working directly with the founding team.
- **Work Model**: Hybrid (Seattle office) and remote options available depending on role (e.g., Solutions Engineer West Coast remote, Mid-Market AE Seattle hybrid).
- **Perks**: Competitive compensation (cash + commission), strong backing from top-tier investors, and a clear mission-driven focus.
- **Engineering Culture**: Emphasis on failing fast, iterating constantly, and taking bold bets. Team includes alumni from Google, Apple, Microsoft, and Tableau.

## Sources

1. [yoodli.ai - About Us](https://yoodli.ai/about)
2. [yoodli.ai - Homepage](https://yoodli.ai/)
3. [yoodli.ai - Official Information](https://yoodli.ai/info-for-ai)
4. [yoodli.ai - AI Roleplays Platform](https://yoodli.ai/platform/ai-roleplays)
5. [Greenhouse - Yoodli Jobs](https://job-boards.greenhouse.io/yoodliinc)

## Other roles at Yoodli AI Roleplays

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- [Senior Revenue Analyst](https://feeny.ai/job/senior-revenue-analyst-yoodli-ai-roleplays-seattle-awzp3ydgj0g3) — Seattle, WA
- [Director, Revenue Strategy & Operations](https://feeny.ai/job/director-revenue-strategy-operations-yoodli-ai-roleplays-seattle-3c589db1wye7) — Seattle, WA
- [Corporate Counsel](https://feeny.ai/job/corporate-counsel-yoodli-ai-roleplays-united-states-e55t18hgnq0b) — United States
- [Senior Software Engineer- Backend (Platform)](https://feeny.ai/job/senior-software-engineer-backend-platform-yoodli-ai-roleplays-seattle-hge3fdb57r3e) — Seattle, WA
- [Senior Customer Marketing Manager](https://feeny.ai/job/senior-customer-marketing-manager-yoodli-ai-roleplays-seattle-gpnwzbhktxap) — Seattle, WA
- [Fullstack Software Engineer- Analytics](https://feeny.ai/job/fullstack-software-engineer-analytics-yoodli-ai-roleplays-seattle-k6jgvnf9njbe) — Seattle, WA
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- [Senior Partner Manager](https://feeny.ai/job/senior-partner-manager-yoodli-ai-roleplays-united-states-whthk8f2sf9x) — United States
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