Director Enterprise Sales

Brex; British Columbia; Hybrid; CAD 381,000 - 453,000; Full time

Job summary

A technology-driven financial service is seeking a Director of Sales to lead a team of Senior Account Executives in the Enterprise segment. This role involves driving new customer acquisition in a complex, high-stakes environment, managing and mentoring a sales team, and collaborating cross-functionally to unlock high-value opportunities. Candidates should have over 5 years of experience in enterprise sales leadership with a proven track record in B2B environments. The role is based in Canada with flexible remote working options.

Qualifications

• 5+ years of first-line Enterprise sales leadership experience, managing AEs.
• Proven track record in complex B2B sales with long cycles and multiple stakeholders.
• Strong balance of executive presence and tactical execution.

Responsibilities

• Lead, coach, and develop a team of Senior Account Executives focused on complex sales cycles.
• Design and drive systems for outbound rigor, pipeline inspection, and forecast discipline.
• Partner cross-functionally with various teams to align on strategy and implementation.

Skills

Enterprise sales leadership

Complex B2B sales

Deal coaching

Multithreading

Cross-functional collaboration

Job description

Why join us

Brex is the AI-powered spend platform. We help companies spend with confidence with integrated corporate cards, banking, and global payments, plus intuitive software for travel and expenses. Tens of thousands of companies from startups to enterprises — including DoorDash, Flexport, and Compass — use Brex to proactively control spend, reduce costs, and increase efficiency on a global scale.

Working at Brex allows you to push your limits, challenge the status quo, and collaborate with some of the brightest minds in the industry. We’re committed to building a diverse team and inclusive culture and believe your potential should only be limited by how big you can dream. We make this a reality by empowering you with the tools, resources, and support you need to grow your career.

What You’ll Do

As Director of Sales for our Enterprise segment, you will lead a team of 5–7 Account Executives responsible for driving new customer acquisition in our most strategic segment. This role is critical to scaling disciplined execution and deal quality in a highly complex, high-stakes environment.

You’ll coach your team through ambiguous, multi-threaded sales cycles and partner cross-functionally to unlock high-value opportunities. You’ll help shape deal strategy, drive pipeline inspection rigor, and directly engage in critical opportunities to model “what good looks like.” Your success will depend on your ability to balance frontline involvement with executive alignment — while hiring and scaling top-tier talent and reinforcing a culture of ownership and accountability.

Where You’ll Work

This role will be based in one of our Brex offices — San Francisco, New York, Vancouver, or Salt Lake City. Team members are expected to work in-office at least two days per week (Wednesdays and Thursdays). Brex also offers the flexibility to work remotely for up to four weeks per year, in one-week increments.

Responsibilities

• Lead, coach, and develop a team of 45–67 Senior Account Executives focused on complex, multi-stakeholder sales cycles
• Hire, onboard, and scale an Enterprise AE team with a strong emphasis on accountability, execution rigor, and high standards of performance
• DesignImprove and drive systems for outbound rigordeal rigor, pipeline inspection, and forecast discipline
• Partner cross-functionally with Product, Marketing, Customer Success, Enablement, and Pricing to align on roadmap gaps, pricing strategy, and implementation readiness
• Play a hands-on role in deal progression — helping unblock critical opportunities and providing strategic guidance to your team
• Serve as a trusted thought partner to the VP of Sales, helping absorb execution complexity while upleveling team operations and morale
• Promote a performance culture rooted in accountability, ownership, and continuous learning
• Bring clarity to deals in motion and remove organizational blockers

Requirements

• 5+ years of first-line Enterprise sales leadership experience; direct management of AEs required
• Proven track record in complex B2B sales environments with long cycles, multiple stakeholders, and internal friction
• Skilled at multithreading, deal coaching, and navigating internal influence
• Thrives in ambiguity; able to simplify complex problems and communicate with precision
• Comfortable delivering results in environments with evolving product-market fit
• Experience partnering cross-functionally with Product, Customer Success, Pricing, and Marketing
• Strong balance of executive presence and tactical execution
• Low-ego, high-ownership leader who leads with clarity, accountability, and team-first mindset

Compensation

The expected OTE range for this role is $280,000 - $332,500. The starting wage will depend on a number of factors including the candidate’s location, skills, experience, market demands, and internal pay parity. The OTE figure listed here includes base salary and commissions, which may or may not be earned depending on performance. Depending on the position offered, equity and other forms of compensation may be provided as part of a total compensation package.

Please be aware, job-seekers may be at risk of targeting by malicious actors looking for personal data. Brex recruiters will only reach out via LinkedIn or email with a brex.com domain. Any outreach claiming to be from Brex via other sources should be ignored.