Yoodli AI Roleplays - Mid-Market Sales Leader
Requirements
• 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
• Team Leadership • 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 • Sales Execution & Forecasting • Own the mid-market number, including pipeline generation, progression, and quota attainment • Forecast accurately with clear visibility into coverage, stage health, and risk • Inspect deals with structure and remove blockers quickly • Drive consistent execution on mutual action plans, recaps, and next-step discipline • Cross-Functional Partnership • 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 • You're a Fit If You… • Have 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 • Have led teams running mid-market or commercial deal cycles (typically 30-120 days, $25K-$200K ACV) • Bring strong coaching instincts and know how to make reps better through repetition, feedback, and structure • Forecast with discipline and inspect deals without micromanaging • Have 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 • 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
Benefits
• ○ 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
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