Senior Director, Sales - Mid-Market (West/Central)

Who We Are

At the company, you’ll not just imagine the future – you’ll build it. As a leader in expense intelligence, we are creating a future where technology drives business value and inspires extraordinary results. Our AI-powered platform helps organizations modernize financial operations, increase visibility, and optimize spend across the enterprise.

The company is looking for a Senior Director of Mid-Market Sales to lead and scale our new logo business across North America (U.S. and Canada), focused on companies with 1,000–3,500 employees.

This is a high-impact leadership role in a growth-stage environment. The foundation is in place, and now we’re looking for a leader who can elevate execution, strengthen pipeline rigor, and scale a repeatable, high-performing sales motion.

You’ll lead a team of Account Executives selling into the office of the CFO, navigating complex, multi-stakeholder deals across a comprehensive financial operations platform. Success in this role requires a leader who is equally comfortable building structure and rolling up their sleeves — someone who can quickly assess gaps, implement discipline, and coach a team to consistently win.

What You Will Do

Lead & Scale the Team

• Lead, develop, and inspire a team of Mid-Market Account Executives focused on new logo acquisition

• Build a high-performance culture grounded in accountability, ownership, and continuous improvement

• Recruit, onboard, and ramp talent as the team continues to grow

Drive Pipeline & Execution Discipline

• Establish and enforce a strong operating cadence around pipeline generation, deal progression, and forecast accuracy

• Ensure consistent pipeline creation , including rep-driven prospecting in addition to marketing support

• Implement and maintain disciplined forecasting and deal inspection frameworks

Coach for Complex Sales

• Coach reps on multi-threaded deal strategy , including stakeholder mapping and value articulation

• Actively engage in and support large, complex deals with longer sales cycles

• Elevate the team’s ability to sell multi-product, solution-based value in competitive environments

Engage Executive Stakeholders

• Partner with reps to engage CFOs, Controllers, and senior finance leaders

• Help position the company’s platform across travel, expense, AP/invoice, payments, and corporate cards

• Drive strong executive-level conversations that align to business outcomes

Partner Cross-Functionally

• Collaborate with Marketing, SDRs, Solutions Consulting, Customer Success, and Partnerships

• Align go-to-market efforts to improve pipeline quality, conversion, and overall performance

• Drive coordinated execution across the customer lifecycle

What You Will Bring

• 7+ years of sales leadership experience in SaaS or technology organizations

• 8+ years of overall sales experience in complex, solution-based selling environments

• Proven success leading Mid-Market or Enterprise teams with longer sales cycles and multi-stakeholder deals

• Strong coaching capability, particularly in deal strategy, pipeline development, and execution rigor

• Demonstrated experience building and maintaining forecast discipline and pipeline inspection frameworks

• Deep familiarity with Salesforce (or equivalent CRM) for pipeline management and forecasting

• Experience selling into or coaching teams selling into the office of the CFO

• Ability to operate effectively in a fast-paced, high-growth environment

Preferred

• Background in fintech, payments, or financial operations platforms

• Experience scaling teams or building repeatable sales motions

• Experience leading geographically distributed teams

Who You Are

• A builder and operator — you know how to create structure, but you’re equally comfortable refining and improving what exists

• Highly execution-focused , with a strong bias toward action and accountability

• Skilled at balancing strategic thinking with hands-on leadership

• A strong coach who can break down deals, guide reps through complexity, and elevate team performance

• Comfortable in environments that require adaptability, agility, and continuous iteration

• Data-driven, with a sharp focus on pipeline health, forecasting accuracy, and performance metrics

• Confident engaging senior stakeholders and building credibility with both customers and internal partners

Why the company?

Finance is changing—and at the company, we’re leading the way. Our AI-powered solutions help organizations eliminate inefficiencies, gain real-time visibility, and optimize spend—so they can focus on what’s next, not what’s slowing them down.

• A Company with Momentum – We serve 12M+ users across 120 countries, helping businesses modernize

their finance operations.

• A Team That Innovates – Work alongside some of the brightest minds in finance, tech, and AI to solve real-

world challenges.

• A Culture That Empowers – Competitive pay, flexible work, and an inclusive, collaborative environment that

supports your success.

• A Career That Matters – Your work here drives efficiency, innovation, and smarter financial decision-making

for businesses everywhere.

Shape your future & find what’s next at the company.

The company provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability or genetics. In addition to federal law requirements, the company complies with applicable state and local laws governing nondiscrimination in employment in every location where the company has facilities. This policy applies to all terms and conditions of employment.