Senior Director, Mid Market Sales
About The Position
Brex is hiring a Senior Director of Sales to lead its Mid-Market organization. This second-line leadership role oversees four frontline sales leaders and approximately 20 Account Executives, owns segment performance, develops the management team, and shapes the strategy and operating cadences for the segment’s next phase of growth. The role reports to the SVP of Sales. The leader will combine strategic planning with hands-on sales leadership: coaching managers, developing talent, and building repeatable systems for pipeline generation, forecast accuracy, and consistent deal execution. The role establishes priorities and guides teams through growth and change while fostering accountability, ownership, and collaboration. In partnership with go-to-market functions, the leader will help the organization win competitive deals and extend successful approaches across the segment. The position is based in one of Brex’s offices in San Francisco, New York City, Seattle, or Salt Lake City. Brex’s hybrid environment requires at least three office days each week—Monday, Wednesday, and Thursday—and offers up to four weeks per year of fully remote work.
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.
- Experience selling to finance buyers.
- Experience with partner-led selling.
- Leadership experience spanning new business and post-sale.
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.
Benefits
- Hybrid work environment with up to four weeks per year of fully remote work.
- Equity and other forms of compensation may be provided, depending on the position offered.
Stand Out From the Crowd
Upload your resume and get instant feedback on how well it matches this job.
What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
