Mid-Market Sales Leader

Yoodli AI Roleplays

Mid-Market Sales Leader responsible for building and leading a sales team at Yoodli. Driving sales growth for mid-market segment through team coaching and strategic partnerships.

Posted 6/3/2026full-timeSeattle • Washington • 🇺🇸 United StatesSenior💰 $280,000 - $300,000 per yearWebsite

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

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.

Benefits

Comp & perks

Equity: Meaningful early-stage options

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

B2B SaaSquota attainmentsales methodologyMEDDICChallengerpipeline generationdeal executionnegotiationforecastingKPI

Soft Skills

coachingcommunicationaccountabilitycuriositycontinuous improvementfeedbackstructurecollaborationleadershipadaptability