Yoodli AI Roleplays

Yoodli AI Roleplays

Mid-Market Sales Leader

Remote (U.S.A.) · Mid

Sponsorship not specified$30k-$120kDetected 27 days ago
SnowflakeDatabricksHubSpotSalesNegotiationForecastingCustomer SuccessLeadershipCommunicationMentoring

About the role

  • 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.

Responsibilities

  • Recruit, develop, and retain top-performing Mid-Market AEs
  • Build a culture of accountability, curiosity, and continuous improvement, using Yoodli itself as a coaching tool
  • Own the mid-market number, including pipeline generation, progression, and quota attainment
  • Drive consistent execution on mutual action plans, recaps, and next-step discipline
  • Partner with Marketing on segment-specific plays, campaigns, and messaging
  • Collaborate with Product and Customer Success to shape roadmap input and ensure clean handoffs

Requirements

  • Have 1-3 years of experience managing B2B SaaS Account Executives, with a track record of leading reps to consistent quota attainment

Compensation

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

Benefits

  • Forecast accurately with clear visibility into coverage, stage health, and risk
  • ○ Equity: Meaningful early-stage options

Company info

  • Yoodli 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"
  • Yoodli 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.
  • Explainer on experiential learning
  • 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.
  • 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.
  • Team Leadership
  • Coach reps on discovery, multi-threading, demo execution, and negotiation
  • Run weekly 1:1s, deal reviews, and pipeline reviews with rigor
  • Sales Execution & Forecasting
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This listing is sourced directly from Yoodli AI Roleplays's careers page and normalized into a canonical job model.