Senior Director of Mid Market Sales

• As Senior Director of Sales for the Mid-Market segment, you will lead Brex’s Mid-Market organization, overseeing four frontline sales leaders and ~20 Account Executives
• Reporting to the SVP of Sales, you’ll own segment performance, develop the management team, and shape the strategy and operating cadences that support the organization’s next phase of growth
• This is a second-line leadership role that combines strategic planning with hands-on sales leadership. You’ll coach managers, develop exceptional talent, and build repeatable systems that drive pipeline generation, forecast accuracy, and consistent deal execution
• You’ll establish clear priorities and lead teams through growth and change while fostering a culture of accountability, ownership, and collaboration. Working across go-to-market functions, this leader will empower the organization to win competitive deals and translate successful approaches into stronger execution across the segment
• 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

• Medical, dental & vision
• Generous vacation
• Spring Health & Calm
• Year-end company shutdown
• Milk Stork for nursing parents
• In-office days, lunches & offsites
• Commuter benefits
• 4 fully remote weeks
• Carrot Fertility benefits
• Generous parental leave

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 required3+ years of experience managing managers in a second-line sales leadership role, with measurable business results delivered through the frontline management teamA proven approach to hiring, coaching, and performance management, along with experience leading teams through meaningful growth or organizational change

Clear communication and sound judgment under ambiguity; comfortable setting strategic direction while staying close to customers, managers, and execution

Strong sales judgment and competitive-selling experience, with the ability to coach managers through qualification, stakeholder engagement, differentiation, and complex deal decisions
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

Strong cross-functional leadership skills, with examples of aligning stakeholders, navigating disagreement, and delivering shared business outcomes

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