Mid-Market Sales Leader

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