Mid-Market Account Executive (Hybrid – Seattle)

Yoodli AI Roleplays•Seattle, WA

8d•Hybrid

About The Position

Yoodli is the AI roleplay simulator redefining how individuals and teams master communication. 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. We’re building a new category called Experiential Learning: a new AI-powered category that helps people learn through conversational roleplays. Yoodli makes that process interactive, personalized, and always up to date. We’ve $40M in Series B funding, doubling our team in 2026, and are headquartered at the beautiful Pier 70 in Seattle. 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.

Requirements

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

Nice To Haves

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

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 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 RevOps, Customer Success, and Marketing to improve handoffs and customer outcomes
Share market feedback and contribute to evolving sales playbooks and messaging