---
title: 'Mid-Market Sales Leader at Yoodli AI Roleplays'
canonical: 'https://feeny.ai/job/mid-market-sales-leader-yoodli-ai-roleplays-united-states-2q7410sycqhk'
type: 'job'
last_seen: '2026-09-15'
---

# Mid-Market Sales Leader at Yoodli AI Roleplays

- **Company:** Yoodli AI Roleplays
- **Location:** United States
- **Work type:** remote
- **Posted:** 2026-06-03
- **Last confirmed live:** 2026-09-15
- **Apply:** https://job-boards.greenhouse.io/yoodliinc/jobs/4272491009

## 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 Sales Leader to build and lead the team that drives Yoodli's fastest-growing segment. You'll report to the Head of GTM and own the number for mid-market, the segment that sits between our high-velocity SMB motion and our strategic Enterprise motion.

This is a pure leadership role. You won't carry an individual quota. Instead, your job is to make every rep on your team better, faster. You'll hire, coach, forecast, and operate the team with discipline while shaping the playbook that makes mid-market a repeatable engine for Yoodli.

You'll lead a team of 4-6 Mid-Market Account Executives running consultative, multi-threaded sales cycles. You'll work closely with Sales Leadership, RevOps, Marketing, Customer Success, and Solutions Engineering to land and expand high-potential accounts, and you'll partner with the Enterprise and SMB leaders to define how segments hand off and scale together.

## What You'll Do

## Team Leadership

- Recruit, develop, and retain top-performing Mid-Market AEs
- Coach reps on discovery, multi-threading, demo execution, and negotiation
- Run weekly 1:1s, deal reviews, and pipeline reviews with rigor
- Build a culture of accountability, curiosity, and continuous improvement, using Yoodli itself as a coaching tool

Sales Execution & Forecasting

- Own the mid-market number, including pipeline generation, progression, and quota attainment
- Forecast accurately with clear visibility into coverage, stage health, and risk
- Apply MEDDIC, Challenger, or similar value-based methodologies as core principles guiding how the team qualifies, strategizes, and closes
- Inspect deals with structure and remove blockers quickly
- Drive consistent execution on mutual action plans, recaps, and next-step discipline

Cross-Functional Partnership

- Partner with Marketing on segment-specific plays, campaigns, and messaging
- Collaborate with Product and Customer Success to shape roadmap input and ensure clean handoffs
- Work with RevOps to refine systems, dashboards, and KPIs that scale with the segment
- Coordinate with SMB and Enterprise leaders to define segmentation, routing, and graduation criteria

You're a Fit If You…

- Have 1-3 years of experience managing B2B SaaS Account Executives, with a track record of leading reps to consistent quota attainment
- Spent meaningful time as a top-performing AE before moving into management
- Have led teams running mid-market or commercial deal cycles (typically 30-120 days, $25K-$200K ACV)
- Bring strong coaching instincts and know how to make reps better through repetition, feedback, and structure
- Forecast with discipline and inspect deals without micromanaging
- Have implemented or scaled a sales methodology (e.g., MEDDIC, Challenger) on a team
- Operate well in fast-moving, early-stage environments where the playbook is still being written
- Care deeply about communication, learning, and the potential of AI to unlock human performance

Bonus Points

- Experience selling to GTM, Enablement, L&D, RevOps, or HR leaders
- Familiarity with tools like Gong, Outreach, HubSpot, Clay, and AI-assisted sales workflows
- Experience scaling a segment from early playbook through repeatable execution
- Background spanning both early-stage and scaled GTM organizations

Competitive compensation:

○ On Target Earnings: $280,000 - $300,000 (50/50 commission to uncapped variable)

○ Equity: Meaningful early-stage options

## 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

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- [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
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