Senior Director, Mid Market Sales

Brex•New York, NY

1d•$343,520 - $429,400•Hybrid

About The Position

Brex is seeking a Senior Director of Sales for the Mid-Market segment to lead their Mid-Market organization. This role will oversee four frontline sales leaders and approximately 20 Account Executives. Reporting to the SVP of Sales, the successful candidate will be responsible for segment performance, developing the management team, and shaping the strategy and operating cadences to support the organization's growth. This is a second-line leadership role that requires a blend of strategic planning and hands-on sales leadership. The role involves coaching managers, developing talent, and building repeatable systems for pipeline generation, forecast accuracy, and consistent deal execution. The leader will establish clear priorities, guide teams through growth and change, and foster a culture of accountability, ownership, and collaboration. Collaboration with go-to-market functions will be key to empowering the organization to win competitive deals and improve execution across the segment.

Requirements

10+ years of B2B sales experience, with demonstrated success in Mid-Market or comparable upmarket environments and a consistent record of meeting or exceeding revenue targets
3+ years of experience managing managers in a second-line sales leadership role, with measurable business results delivered through the frontline management team
Strong operating and analytical rigor, including experience building forecasting, pipeline management, and inspection systems that improve execution and predictability
Experience leading outbound-oriented sales teams and helping sellers prioritize large books of accounts while maintaining deal velocity
Strong sales judgment and competitive-selling experience, with the ability to coach managers through qualification, stakeholder engagement, differentiation, and complex deal decisions
A proven approach to hiring, coaching, and performance management, along with experience leading teams through meaningful growth or organizational change
Strong cross-functional leadership skills, with examples of aligning stakeholders, navigating disagreement, and delivering shared business outcomes
Clear communication and sound judgment under ambiguity; comfortable setting strategic direction while staying close to customers, managers, and execution

Nice To Haves

Experience in fintech or spend management, selling to finance buyers, partner-led selling, or leadership spanning new business and post-sale is helpful but not required

Responsibilities

Lead, coach, and develop frontline sales managers to consistently achieve Mid-Market new-business targets
Own segment strategy and execution, translating business priorities into clear goals, manager expectations, and measurable outcomes
Hire and develop exceptional sales talent, build leadership bench strength, and maintain a high bar for coaching and performance management
Build and scale operating cadences across outbound prospecting, account prioritization, pipeline inspection, deal reviews, and forecasting
Use data to diagnose performance gaps, prioritize improvements, and measure their impact on pipeline quality, conversion, and sales productivity
Coach managers on qualification, competitive differentiation, and strategic deal execution; participate in key customer opportunities while strengthening the team’s ability to win independently
Partner with Sales Development, Marketing, Product Marketing, Revenue Operations, Enablement, Product, and post-sale teams to generate pipeline, remove friction, and deliver on customer commitments
Lead teams through growth and change by communicating clear priorities, building commitment, and reinforcing consistent execution and accountability
Model ownership, urgency, humility, and a company-first mindset while contributing to broader go-to-market initiatives