---
title: 'Enterprise Account Executive at Yoodli AI Roleplays'
canonical: 'https://feeny.ai/job/enterprise-account-executive-yoodli-ai-roleplays-united-states-n1d622ecg7ks'
type: 'job'
last_seen: '2026-10-27'
---

# Enterprise Account Executive at Yoodli AI Roleplays

- **Company:** Yoodli AI Roleplays
- **Location:** United States
- **Work type:** remote
- **Posted:** 2026-10-24
- **Last confirmed live:** 2026-10-27
- **Apply:** https://job-boards.greenhouse.io/yoodliinc/jobs/4466564009

## Job description

Who we are:

Yoodli is a venture-backed company building an AI Platform for Human Skills, helping people get measurably better in their careers by supporting them in the flow of work.

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, a bias for action, and the belief that we win together.

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. We're valued at $300M and grew revenue 900% year over year.

Our customers include Google Cloud, Snowflake, Databricks, RingCentral, SAP, FranklinCovey, Korn Ferry, Sandler Training, Toastmasters, and many more, with learners in over 150 countries. Google Cloud certified 15,000+ reps without scaling headcount. Snowflake recovered 1,200+ manager hours per quarter. Harness cut training review time by 75%.

We've been featured in TechCrunch, Axios, The Information, Forbes, Fast Company, and more. Try the platform free at [yoodli.ai](http://yoodli.ai/).

The Role:

We’re hiring an Enterprise Account Executive to help drive Yoodli through this next inflection point. You’ll lead consultative sales cycles across mid-market and enterprise segments. You’ll own the full sales process - from first conversation to signed contract - using deep discovery, value-based selling, incredible demo skills and a Challenger mindset. Your passion for helping others grow through communication is evident throughout.

You’ll work closely with Leadership, Solutions Engineering, Marketing, and Customer Success to land and expand accounts that shape the future of our platform. This is a high-trust, high-autonomy role ideal for someone who blends curiosity, grit, and a mission-driven mindset.

## About You

- 8+ years in B2B SaaS sales with a track record of consistent quota attainment
- High emotional intelligence—you can detect buyer apathy and adapt quickly
- Skilled in signal recognition, objection handling, and managing next steps with discipline
- Experienced in MEDDIC, Challenger, or similar value-based methodologies
- Comfortable respectfully challenging buyer assumptions to create urgency
- Treats pipeline and forecast like an operator, not a speculator
- Team-first mindset—you're coachable, iterative, and eager to help others win

Bonus Points

- Experience selling to GTM leaders (enablement, L&D, revops)
- Familiarity with tools like Gong, Outreach, Clay, or HubSpot, and incorporating AI into your sales workflow

Responsibilities:

- Own full-cycle sales for enterprise accounts
- Run deep, rigorous discovery to understand buyer challenges and connect to Yoodli’s differentiated value
- Lead multi-threaded sales motions across economic, technical, and operational stakeholders
- Deliver compelling, ROI-driven narratives that shift focus from product to transformation
- Partner with RevOps, SEs, and CS to ensure smooth handoffs and long-term customer success
- Build pipeline via outbound, partnerships, and demand follow-up
- Contribute to a high-performing, collaborative sales culture that lives our values

## Why Yoodli

- Sell a mission-driven product that’s redefining how people communicate

- Work alongside a seasoned founding team and world-class investors

- Shape the DNA of an early-stage sales team and playbook

- Competitive compensation:

- Base Salary: $130K-$150K
- Variable OTE: $130K-$150K
- Equity: Meaningful early-stage options

- Full benefits: healthcare, dental, vision, 401k, flexible PTO

- [Learn more about our team values and culture](https://yoodli.ai/about)

## 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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