Senior Director, Mid-Market Sales & Growth

WinsAbove; New York (NY); Hybrid; USD 344,000 - 429,000; Full time

Benefits offered by this job

Hybrid work model

Remote work up to 4 weeks per year

Job summary

Brex is seeking a Senior Director of Sales for the Mid-Market segment to lead four frontline sales leaders and ~20 Account Executives. You will shape strategy, coach managers, and build scalable processes to drive pipeline, forecast accuracy, and deal execution.

This second-line leadership role centers on strategic planning and hands-on coaching across GTM functions. Base in SF/NYC/Seattle with hybrid work and flexible remote time.

Qualifications

• 10+ years of B2B sales experience in Mid-Market or upmarket environments.
• 3+ years of experience managing managers in a second-line sales leadership role.
• Strong operating and analytical rigor, including forecasting, pipeline management, and inspection systems.
• Experience leading outbound-oriented sales teams and prioritizing large books of accounts while maintaining deal velocity.
• Strong sales judgment and competitive-selling experience; ability to coach through qualification and complex deals.
• Proven hiring, coaching, and performance management abilities; leading teams through growth or change.
• Strong cross-functional leadership with stakeholder alignment and execution.
• Clear communication and sound judgment under ambiguity; comfortable setting strategic direction.
• Experience in fintech or spend management is helpful but not required.

Responsibilities

• Lead, coach, and develop frontline sales managers to consistently achieve Mid-Market targets.
• Own segment strategy and execution with clear goals, manager expectations, and measurable outcomes.
• Hire and develop sales talent, build leadership bench strength, and maintain coaching standards.
• Build and scale operating cadences across outbound prospecting, pipeline inspection, forecasting, and reviews.
• Use data to diagnose performance gaps and measure impact on pipeline quality and sales productivity.
• Coach on qualification, differentiation, and strategic deal execution; participate in key opportunities.
• Partner with Sales Development, Marketing, Product Marketing, Revenue Ops, Enablement, Product, and post-sale teams to drive pipeline and remove friction.
• Lead teams through growth with clear priorities and accountability; contribute to broader go-to-market initiatives.

Skills

Sales leadership

Forecasting

Pipeline management

Cross-functional

Coaching managers

Deal strategy

Tools

CRM systems

Job description

Brex is seeking a Senior Director of Sales for the Mid-Market segment to lead four frontline sales leaders and ~20 Account Executives. You will shape strategy, coach managers, and build scalable processes to drive pipeline, forecast accuracy, and deal execution.

This second-line leadership role centers on strategic planning and hands-on coaching across GTM functions. Base in SF/NYC/Seattle with hybrid work and flexible remote time.