Mid-Market Account Executive

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, 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”

Explainer on 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