Mid-Market Account Executive

Yoodli AI Roleplays; Seattle (WA); On-site; USD 200,000 - 240,000; Full time

Benefits offered by this job

Healthcare

Dental

Vision

401k

Flexible PTO

Job summary

Yoodli, a Seattle-based AI platform, is seeking a Mid-Market Account Executive to drive growth across mid-market accounts. You will own consultative sales from discovery to signed contract with strong demos and ROI storytelling.

Collaborate with RevOps, Customer Success, and Marketing; thrive in a high-growth environment delivering both transactional and enterprise sales. In-person work at AI House 3+ days a week in Seattle.

Qualifications

• Proven ability to uncover pain and map to outcomes.
• Clear communication and stakeholder alignment.
• Manage multiple opportunities with quality and speed.
• Experience with MEDDIC or Challenger like frameworks.

Responsibilities

• Own full-cycle mid-market sales across accounts.
• Conduct discovery to connect challenges to Yoodli value.
• Lead multi-threaded conversations with business, tech, ops.
• Deliver demos and ROI narratives to position Yoodli strategically.

Skills

Discovery skills

Communication

Multi-threading

Forecasting

CRM hygiene

Coachable

Relocation-ready

Tools

Gong

Outreach

HubSpot

Clay

Job description

Yoodli helps people get measurably better in their careers. We help individuals achieve this by helping them land their job, onboard at their companies, learn new skills, practice a speech, sales pitch or difficult conversation, and then take your Yoodli coach with you from one role to the next. For organizations, this means helping you upskill your entire workforce for the AI Future.

We’ve always believed in the human potential. In 2021, Esha and Varun started Yoodli as an AI communication coach - to help people communicate with confidence. Since then, our users have used Yoodli for so much more: to learn new concepts through AI Roleplays, practice different kinds of conversations (sales pitches, job interviews, manager conversations), and even use Yoodli as their personal coach to help them learn to use Gemini, Claude or other AI Tools. It’s why we expanded our technology to be the AI Platform for Human Skills.

Who We Are

Our team includes former employees from Google, Apple, Microsoft, Tableau, and beyond, united by a passion for empowering people using AI. We're headquartered in the heart of Seattle, and we're having a lot of fun along the way. Our culture is built on failing fast, iterating constantly, and taking bold bets. We value humility, authenticity, and a can-do-attitude.

We’re backed by Madrona, Neotribe the Allen Institute for AI, Cercano, and have raised over $60M to date.

Our customers include Google, RingCentral, Databricks, Snowflake, Sandler Sales, Dale Carnegie, Toastmasters, and users in over 150 countries. We’ve been featured in Forbes, Fortune, WSJ, Geekwire, ZDNet, and several other outlets (www.yoodli.ai/press). You can try the platform for free at www.yoodli.ai and learn more about us in this TED Talk.

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 learn and practice new skills
• Work alongside a seasoned founding team and world-class investors
• Shape the future of an early-stage GTM organization and category-defining company