We are seeking a leader who will not simply manage the existing organization but will help define the next chapter of sales leadership at Top Hat. The next Director will be required to raise standards, develop future leaders, and shape what excellence looks like for a modern, high-performing revenue organization.

Unlike many Director roles that are removed from customers and frontline execution, this position offers the opportunity to shape strategy, develop leaders, and remain closely connected to the market, the team, and the customer experience.

Location & Travel Requirements

This position requires approximately 30% of your time to be spent on campus during the busy sales seasons, from mid-January through May and mid-August through mid-December.

Due to the travel requirements of this role, we are looking for candidates located within the Western region of the US. Eligible hubs include Austin, Dallas, Houston, Phoenix, Portland, Seattle, Sacramento, San Francisco and Los Angeles. Ideal candidates must live within proximity to a major airport to facilitate efficient travel.

Leadership Competencies:

• Builds accountable, collaborative, and inclusive team cultures where individuals are supported, challenged, and developed.

• Creates clarity amid ambiguity and aligns teams around priorities, execution, and measurable outcomes.

• Balances strategic thinking with a willingness to engage directly in deal strategy, coaching, talent development, and problem-solving.

• Uses data, customer insights, and market intelligence to inform decisions and improve team performance.

• Demonstrates sound judgment, resilience, and adaptability in complex and evolving business environments.

• Raises the performance standard by defining and reinforcing what excellence looks like for individuals, managers, and teams.

Required Experience & Qualifications:

• 15+ years of progressive sales with 5+ years of sales leadership or people management experience within EdTech, higher education courseware, SaaS, or related industries.

• Demonstrated success leading geographically distributed sales organizations and consistently achieving revenue targets.

• Proven track record of recruiting, developing, coaching, and retaining high-performing sales professionals and sales leaders.

• Experience managing both direct reports and people leaders within a multi-layered sales organization.

• Strong background in forecasting, pipeline management, territory planning, and performance management.

• History of successfully leading teams through organizational change, go-to-market evolution, and periods of rapid growth or transformation.

• Demonstrated ability to partner effectively across Marketing, Customer Success, Product, Content, Finance, and Revenue Operations to drive business outcomes.

• Excellent communication, coaching, and executive presence, with the ability to influence at all levels of the organization.

Preferred Qualifications:

• Experience scaling sales organizations through significant growth, transformation, or market expansion.

• Proven ability to develop future leaders and build leadership bench strength.

• Experience operating within complex, matrixed organizations where influence and alignment are critical to success.

• A track record of improving sales productivity, forecasting accuracy, pipeline quality, and operational rigour.

• Ability to elevate the function by establishing new standards, processes, and expectations that improve organizational performance over time.

Why team members love working at Top Hat:

• A noble mission that creates meaningful, fulfilling work

• A team that cares deeply for customers and for each other

• Flexible, remote first work environment

• Professional learning and development for all role levels

• An awesome and welcoming Toronto HQ

• Competitive health benefits that start on day one

• A management team focused on performance, growth, engagement and connection

• Our winning strategy and market potential

• Innovative PTO policy with lots of time and space for self-care

• Passionate customers that believe in us—and what we do

• A chance to work with new tech like generative AI—and see the customer impact