---
title: 'Mid-Market Account Executive at Yoodli AI Roleplays'
canonical: 'https://feeny.ai/job/mid-market-account-executive-yoodli-ai-roleplays-seattle-jb5jqpzb5pgz'
type: 'job'
last_seen: '2026-09-15'
---

# Mid-Market Account Executive at Yoodli AI Roleplays

- **Company:** Yoodli AI Roleplays
- **Location:** Seattle, WA
- **Work type:** hybrid
- **Posted:** 2026-05-18
- **Last confirmed live:** 2026-09-15
- **Apply:** https://job-boards.greenhouse.io/yoodliinc/jobs/4251596009

## Job description

Who we are:

[Yoodli](http://www.yoodli.ai/) is the AI roleplay simulator redefining how individuals and teams master communication. Think of it as the batting cage before the big game - but for communication. Whether it’s a sales pitch, manager feedback session, or media interview, Yoodli provides private, judgment-free, just-in-time coaching. Leaders at companies like Google, Databricks, Snowflake, RingCentral, Toastmasters, and Dale Carnegie use Yoodli to ramp reps faster, improve message delivery, and reduce coaching burden on frontline managers. The result is stronger performance, greater team readiness, and a more scalable path to impact.

We’re building a new category called Experiential Learning: a new AI-powered category that helps people learn through conversational roleplays. People don’t learn from slides: they learn through dialogue, questions, and iteration. Yoodli makes that process interactive, personalized, and always up to date. It’s learning that feels fun, builds confidence, and finally lets organizations measure the ROI of training.

We’ve $40M in Series B funding, doubling our team in 2026, and are headquartered at the beautiful Pier 70 in Seattle.

- [TED Talk with our “Why”](https://www.youtube.com/watch?v=9CVsdayG2kw)
- [Explainer on experiential learning](https://yoodli.ai/blog/yoodli-raises-40-million-series-b-to-lead-the-future-of-experiential-learning)

The Role:

We're hiring a Mid-Market Account Executive to help drive Yoodli through this next stage of growth. You'll own consultative sales cycles across mid-market accounts, balancing velocity with strategic execution. You'll manage the full sales process from first conversation to signed contract using strong discovery, value-based selling, compelling demos, and disciplined follow-through.

This role sits between our SMB and Enterprise motions: fast enough to reward urgency and creativity, while strategic enough to require multi-threading, thoughtful qualification, and business-case development.

You'll work closely with Sales Leadership, Marketing, Customer Success, and Solutions Engineering to land and expand high-potential accounts. This is a strong fit for someone who thrives in high-growth environments and wants to sharpen both transactional and enterprise-selling muscles.

## Responsibilities

- Own full-cycle sales across mid-market accounts
- Run thoughtful discovery to understand customer challenges and connect them to Yoodli's differentiated value
- Lead multi-threaded conversations across business, technical, and operational stakeholders
- Deliver compelling demos and ROI-driven narratives that position Yoodli as a strategic
- solutionBuild and manage pipeline through outbound prospecting, partnerships, and inbound follow-up
- Maintain disciplined pipeline management, forecasting accuracy, and next-step execution
- Partner closely with RevOps, Customer Success, and Marketing to improve handoffs and customer outcomes
- Share market feedback and contribute to evolving sales playbooks and messaging

## About You

- 4-7 years of experience in B2B SaaS sales with a track record of quota attainment
- Strong discovery and communication skills - you know how to uncover pain, build urgency, and align to business outcomes
- Comfortable managing multiple opportunities simultaneously without sacrificing deal quality
- Experience running consultative sales processes using methodologies like MEDDIC, Challenger, or similar frameworks
- High emotional intelligence - you can read buyer signals and adapt your approach in real time
- Organized and process-oriented with strong CRM hygiene and forecasting discipline
- Coachable, collaborative, and energized by continuous improvement
- Based in Seattle or open to relocating - we work in person at AI House 3+ days a week

Bonus Points

- Experience selling to GTM, enablement, L&D, or RevOps leaders
- Familiarity with tools like Gong, Outreach, HubSpot, Clay, or AI-assisted prospecting workflows
- Experience navigating both inbound and outbound sales motions
- Passion for communication, coaching, learning, or AI-driven products

Competitive compensation

- On Target Earnings $200k-$240k (50/50 split between base and uncapped variable) based on experience
- Equity: Meaningful early-stage options
- Full benefits: healthcare, dental, vision, 401k, flexible PTO

## 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 future of an early-stage GTM organization and category-defining company

## 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

- [Technical Account Manager](https://feeny.ai/job/technical-account-manager-yoodli-ai-roleplays-united-states-58t0gqykq9k3) — United States
- [Senior Software Engineer- Backend (Roleplays)](https://feeny.ai/job/senior-software-engineer-backend-roleplays-yoodli-ai-roleplays-seattle-n851z1p1dv6g) — Seattle, WA
- [Senior Software Engineer- Backend (Product & Cloud Security)](https://feeny.ai/job/senior-software-engineer-backend-product-cloud-security-yoodli-ai-roleplays-6t442ac5sy4n) — Seattle, WA
- [Director of Customer Education](https://feeny.ai/job/director-of-customer-education-yoodli-ai-roleplays-seattle-wa-or-san-francisco-rrrtkhd3xkcw) — Seattle WA OR San Francisco, CA
- [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
- [Deal Desk Lead](https://feeny.ai/job/deal-desk-lead-yoodli-ai-roleplays-seattle-e1dw687468st) — Seattle, WA
- [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