Senior Director, Sales

KEV Group • Toronto, ON

107d

About The Position

As we continue to grow, we are looking for an exceptional Senior Director of Sales to lead and inspire a team of Account Executives (AEs). This role is pivotal in driving success across K-12 territories in the U.S. through collaboration, precise forecasting, pipeline development, and consistent attainment of growth targets. The ideal candidate will be a natural leader, a trusted advisor, and a performance-focused strategist with a proven track record in sales leadership and deep knowledge of the industry.
You’re not just a leader, you’re a multiplier. You drive performance with insight and empathy, knowing when to coach, when to challenge, and when to roll up your sleeves. If you’re ready to take on a high-impact role and lead a dynamic team to measurable success, we’d love to hear from you.

Requirements

• 8+ years of progressive sales experience, including experience working in the K-12 sector
• 3+ years of sales leadership experience
• Demonstrated ability to meet or exceed sales targets consistently, both as an individual contributor and as a leader
• Deep understanding of the sales process, including pipeline nurturing and relationship-building
• Hands-on experience with Salesforce CRM and other sales enablement tools
• A metrics-driven mindset with equal parts strategic and tactical, with the ability to analyze performance metrics, identify challenges, and implement effective action plans
• Exceptional coaching and mentoring skills, with the ability to inspire and motivate teams
• Strong interpersonal skills; approachable, collaborative, and solution oriented
• Ability to travel up to 50% of the time

Responsibilities

• Oversee team attainment against collective quotas and individual sales targets, with a clear focus on pipeline development and deal execution
• Maintain robust monthly and quarterly forecasting, applying data from Salesforce and other tools to drive predictability and precision
• Drive goal attainment and providing visibility and tracking to goals through use of and good CRM hygiene with internal sales tools
• Attend mid-to-large district sales meetings to support AEs and ensure successful outcomes
• Collaborate with marketing to implement and reinforce initiatives and campaigns
• Identify and proactively address performance issues through coaching plans, support strategies, and resource realignment
• Lead, mentor, and inspire a team of AEs to reach and exceed their goals while fostering a culture of accountability, collaboration, and continuous improvement
• Conduct weekly 1:1s to review pipelines, metrics, and conversion trends; use insights to adjust strategies and drive execution
• Coach team members on overcoming challenges, handling objections, and refining sales strategies through mock conversations and scenario practice
• Weekly call reviews with reps to coach them on proper discovery, demo, and closing techniques
• Attract, develop and retain top talent to build a high-performing team
• Facilitate monthly team sessions and cross-functional syncs to reinforce strategy, tools, and shared goals
• Act as a field leader, joining high-impact district meetings and helping the team navigate roadblocks to success
• Leverage key sales and activity metrics (e.g., conversion rates, stage velocity, ACV) to guide decisions and communicate progress to leadership

Benefits

• Competitive compensation – We believe in rewarding great work with fair, competitive pay.
• Meaningful benefits– Because your well-being matters; both at work and at home.
• Retirement Savings Support – We help you plan for your future with company-matched programs, including RRSP matching in Canada and 401(k) contributions in the U.S.
• Professional development – We invest in your growth with ongoing learning, stretch opportunities, and continuing education, including KEV Academy for onboarding and skill-building, plus KEV University, our online platform offering a wide range of courses.
• Flexible PTO – Take the time you need to recharge with close to 4 weeks of vacation and a company-wide holiday closure

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed