Mid-Market Account Executive

Yoodli AI Roleplays; United States; On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Equity: meaningful options

Mission-driven product

World-class investors

Job summary

Yoodli is hiring a Mid-Market Account Executive to drive growth across mid-market accounts. You will own the full sales cycle, from discovery to signed contract, using value-based selling and compelling demos to prove ROI.

This role sits at the intersection of fast velocity and strategic execution, requiring multi-threading, qualification, and business-case development. You’ll collaborate with Sales Leadership, Marketing, CS, and Solutions Engineering.

Qualifications

• 4-7 years of experience in B2B SaaS sales.
• Proven track record of quota attainment.
• Strong discovery and communication skills.
• Experience with MEDDIC, Challenger, or similar frameworks.

Responsibilities

• Own full-cycle sales across mid-market accounts.
• Conduct thoughtful discovery to map pain to value.
• Lead multi-threaded conversations with diverse stakeholders.
• Deliver demos and ROI storytelling to position Yoodli strategically.
• Build and manage pipeline via outbound, partnerships, and inbound follow-up.
• Maintain disciplined forecast and next steps with RevOps and CS.

Skills

B2B SaaS sales

Quota attainment

Discovery & storytelling

CRM hygiene

Tools

Gong

Outreach

HubSpot

Clay

Job description

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

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

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