Director, Sales

About This Role

This leadership role focuses on developing talent, sharpening sales rigor, and building a repeatable, high-performing motion within the mid-market sales organization. You will lead and elevate the team, coaching Account Executives to win complex deals, deepen discovery, improve close rates, and consistently exceed targets.

Responsibilities

• Own mid-market revenue performance, ensuring the team consistently hits and exceeds monthly and quarterly targets
• Coach and develop Account Executives to improve discovery, objection handling, deal strategy, and closing effectiveness
• Elevate call quality through regular deal reviews, call coaching, and structured feedback loops
• Improve pipeline hygiene, forecasting accuracy, and overall sales execution rigor
• Identify skill gaps and implement targeted enablement programs to raise performance across the team
• Refine messaging, positioning, and demo execution to increase conversion rates and ACV
• Lead by example in strategic deals, modeling best-in-class mid-market selling behavior
• Establish clear performance standards and accountability across the team

Requirements

• 6+ years of B2B SaaS sales experience, with 2+ years leading mid-market or enterprise AEs
• Strong track record of improving rep performance through hands-on coaching
• Experience scaling and optimizing mid-market sales motions
• Proven ability to drive forecast accuracy and operational rigor
• Deep expertise in discovery-led, consultative sales
• Ability to diagnose pipeline issues and implement corrective action quickly
• Clear, confident communicator who can raise the bar on performance standards
• High ownership mentality and comfort operating in fast-moving, in-office environments
• Coach first, manager second: you measure your success by how much better your reps get
• Obsessed with deal quality, not just deal volume
• Direct and high-accountability: you don't shy away from tough performance conversations
• Energized by mid-market complexity: real selling skill, fast cycle times, operational discipline
• In the weeds on calls, pipeline, and deal strategy, not managing from a dashboard
• Builder mentality: you want to create something, not maintain it
• High ownership, low ego: you do whatever it takes to make the team win
• In-office, engaged, and eager to lead from the front at our NYC location full-time

Benefits

• Comprehensive medical, dental, and vision insurance
• Company-sponsored 401(k) through Vestwell
• Flexible PTO plus U.S. federal holidays