---
title: 'Commercial Counsel at Yoodli AI Roleplays'
canonical: 'https://feeny.ai/job/commercial-counsel-yoodli-ai-roleplays-united-states-west-coast-e55t18hgnq0b'
type: 'job'
last_seen: '2026-11-03'
---

# Commercial Counsel at Yoodli AI Roleplays

- **Company:** Yoodli AI Roleplays
- **Location:** United States / West Coast
- **Work type:** remote
- **Posted:** 2026-08-14
- **Last confirmed live:** 2026-11-03
- **Apply:** https://job-boards.greenhouse.io/yoodliinc/jobs/4371231009

## Job description

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](http://www.yoodli.ai/press)). You can try the platform for free at [www.yoodli.ai](http://www.yoodli.ai) and learn more about us in this [TED Talk](https://www.youtube.com/watch?v=9CVsdayG2kw).

## The Role

Yoodli is hiring its first dedicated legal hire — someone who can be a genuine business partner, not just a contract reviewer. You'll own the commercial legal function: evaluating risk on customer and vendor agreements, turning redlines efficiently, and giving Sales and RevOps the guidance they need to keep deals moving. The role requires real judgment. You'll run negotiations independently when the situation is routine, know which issues are worth pushing back on and which to let go, and tap outside counsel for matters outside your lane without using them as a crutch. This is a high-visibility role that reports directly to the CFO and has meaningful exposure to nearly every part of the business..

## What You'll Do

- Own the Contract Lifecycle: Serve as the primary reviewer and negotiator for all inbound commercial agreements — customer MSAs, order forms, NDAs, and vendor contracts. You'll manage redlines, track open issues, and shepherd agreements through to signature.
- Be the Business's Legal Partner: Work closely with Sales, RevOps, Finance, and Product on commercial decisions, deal structures, and risk tradeoffs. You'll translate complex legal issues into clear, actionable guidance — helping the business move forward, not just flagging what could go wrong.
- Support Data Privacy and Security Compliance: Review and advise on DPA requirements, security exhibits, and privacy-related contractual obligations across customer and vendor agreements. Keep our standard positions current as the regulatory landscape evolves.
- Build and Maintain Legal Infrastructure: Develop and own a library of standard agreement templates, negotiation playbooks, and fallback positions so the team has consistent guidance on routine issues and doesn't have to reinvent the wheel on every deal.
- Direct Outside Counsel: Scope and manage outside counsel engagements for matters that require deeper or more specialized expertise. Keep work well-defined and costs controlled.
- Streamline How Legal Work Flows: Establish contract intake, tracking, and storage processes that give the business visibility into where things stand and reduce friction for everyone involved.

You Might Be a Fit If You…

- Hold a J.D. from an accredited law school and are licensed to practice in at least one U.S. jurisdiction.
- Have 5 years + of in-house legal experience, with meaningful time spent on commercial contracts in a SaaS or technology company environment.
- Are comfortable running the first few rounds of commercial negotiations independently — you have strong instincts on standard SaaS terms and know when a markup is worth pushing back on versus accepting.
- Have hands-on experience with Data Processing Agreements and a working knowledge of GDPR, CCPA, and other applicable privacy frameworks.
- Know when to bring in outside counsel and can manage those relationships without over-relying on them.
- Have the skills to provide guidance to help reduce the legal risks faced by the company, while also having a good business sense so that such guidance can be properly balanced with the company’s operational goals.
- Communicate legal concepts in plain language and can be a partner to non-lawyers without losing precision.
- Are highly organized, able to manage multiple open deals simultaneously without things falling through the cracks.
- Demonstrate strong skills in negotiations, problem solving, verbal and written communications, and task management and prioritization.
- Thrive in a lean, fast-paced environment and are energized by building structure where there isn't much yet.

## Why Yoodli

- Competitive compensation ($170,000 - $200,000) + 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

#LI-Hybrid

## 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)

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