Mid-Market Account Executive

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Mid-Market Account Executive

Yoodli Ai Roleplays

People Ops

Full-time

Hybrid

Seattle, WA (Hybrid)

Posted on 5/18/2026

Who we are:

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, Ring Central, 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.

• TED Talk with our “Why”
• Explainer on experiential learning

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.

• 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
• solution
  
  Build and manage pipeline through outbound prospecting, partnerships, and inbound follow-up
• Maintain disciplined pipeline management, forecasting accuracy, and next-step execution
• Partner closely with Rev Ops, Customer Success, and Marketing to improve handoffs and customer outcomes
• Share market feedback and contribute to evolving sales playbooks and messaging

• 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

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

• 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

• 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

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