Mid-Market Sales Leader

Yoodli AI Roleplays • Seattle, WA

5h • Hybrid

About The Position

Yoodli is seeking a Mid-Market Sales Leader to build and lead the team responsible for the company's fastest-growing segment. This role reports to the Head of GTM and will be responsible for the mid-market segment, which bridges the gap between the high-velocity SMB motion and the strategic Enterprise motion. This is a leadership position focused on improving the performance of every sales representative on the team. The leader will be responsible for hiring, coaching, forecasting, and operating the team with discipline, while also contributing to the development of the playbook for the mid-market segment. The team will consist of 4-6 Mid-Market Account Executives who manage consultative, multi-threaded sales cycles. Collaboration with Sales Leadership, RevOps, Marketing, Customer Success, and Solutions Engineering is key for landing and expanding high-potential accounts. Partnerships with Enterprise and SMB leaders will be crucial for defining segment handoffs and scaling strategies.

Requirements

• 1-3 years of experience managing B2B SaaS Account Executives, with a track record of leading reps to consistent quota attainment
• Spent meaningful time as a top-performing AE before moving into management
• Led teams running mid-market or commercial deal cycles (typically 30-120 days, $25K-$200K ACV)
• Strong coaching instincts and know how to make reps better through repetition, feedback, and structure
• Forecast with discipline and inspect deals without micromanaging
• Implemented or scaled a sales methodology (e.g., MEDDIC, Challenger) on a team
• Operate well in fast-moving, early-stage environments where the playbook is still being written
• Care deeply about communication, learning, and the potential of AI to unlock human performance
• 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, RevOps, or HR leaders
• Familiarity with tools like Gong, Outreach, HubSpot, Clay, and AI-assisted sales workflows
• Experience scaling a segment from early playbook through repeatable execution
• Background spanning both early-stage and scaled GTM organizations

Responsibilities

• Recruit, develop, and retain top-performing Mid-Market AEs
• Coach reps on discovery, multi-threading, demo execution, and negotiation
• Run weekly 1:1s, deal reviews, and pipeline reviews with rigor
• Build a culture of accountability, curiosity, and continuous improvement, using Yoodli itself as a coaching tool
• Own the mid-market number, including pipeline generation, progression, and quota attainment
• Forecast accurately with clear visibility into coverage, stage health, and risk
• Apply MEDDIC, Challenger, or similar value-based methodologies as core principles guiding how the team qualifies, strategizes, and closes
• Inspect deals with structure and remove blockers quickly
• Drive consistent execution on mutual action plans, recaps, and next-step discipline
• Partner with Marketing on segment-specific plays, campaigns, and messaging
• Collaborate with Product and Customer Success to shape roadmap input and ensure clean handoffs
• Work with RevOps to refine systems, dashboards, and KPIs that scale with the segment
• Coordinate with SMB and Enterprise leaders to define segmentation, routing, and graduation criteria

Benefits

• Competitive compensation
• On Target Earnings: $280,000 - $300,000 (50/50 commission to uncapped variable)
• Equity: Meaningful early-stage options
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed