Mid-Market Sales Leader

Madrona Venture Labs; Seattle (WA); On-site; USD 280,000 - 300,000; Full time

Benefits offered by this job

Equity options

Dynamic work environment

Team-oriented culture

Job summary

Madrona Venture Labs is seeking a Mid-Market Sales Leader to build and lead a team focused on driving Yoodli's fast-growing segment. This leadership role aims at enhancing team performance through coaching and disciplined sales execution.

With competitive compensation between $280,000 and $300,000 OTE, the right candidate will have a strong B2B SaaS background and be passionate about communication and AI.

Qualifications

• 1-3 years of experience managing B2B SaaS Account Executives.
• Top-performing AE background before management.
• Experience with mid-market deal cycles.

Responsibilities

• Recruit and retain top-performing Mid-Market AEs.
• Own mid-market pipeline generation and quota attainment.
• Collaborate with Marketing on plays and campaigns.

Skills

Leadership

Sales Execution

Coaching

B2B SaaS experience

Forecasting

Tools

Sales methodologies (MEDDIC, Challenger)

Job description

Who we are:

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 Sales Leader to build and lead the team that drives Yoodli's fastest-growing segment. You'll report to the Head of GTM and own the number for mid-market, the segment that sits between our high-velocity SMB motion and our strategic Enterprise motion.

This is a pure leadership role. You won't carry an individual quota. Instead, your job is to make every rep on your team better, faster. You'll hire, coach, forecast, and operate the team with discipline while shaping the playbook that makes mid-market a repeatable engine for Yoodli.

You'll lead a team of 4-6 Mid-Market Account Executives running consultative, multi-threaded sales cycles. You'll work closely with Sales Leadership, RevOps, Marketing, Customer Success, and Solutions Engineering to land and expand high-potential accounts, and you'll partner with the Enterprise and SMB leaders to define how segments hand off and scale together.

What You'll Do

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
• 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

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

Bonus Points

• 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

Competitive compensation:

• On Target Earnings: $280,000 - $300,000 (50/50 commission to uncapped variable)
• 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