Senior Director of Sales

Who We Are

At KEV, we help school districts eliminate the school finance blind spot. Our platform gives district finance teams real-time visibility and traceability into every dollar collected at the school level; whether it’s cash, check, or digital. From field trips to fundraisers, we help them manage every dollar with confidence. More than 26,000 schools across North America trust KEV to manage over $4 billion annually. By unifying payments, accounting, and reporting, KEV simplifies life for bookkeepers, builds trust with parents, and gives finance leaders the oversight their current systems cannot. It’s how we help schools stay compliant, reduce risk, and focus on what matters most, student success.

Backed by Five Arrows, the PE arm of Rothschild & Co., KEV is investing more than ever to support K–12 in a world of tighter budgets, rising scrutiny, and fast-changing tech. We’re headquartered in Toronto, with offices across North America.

If you’re excited by the idea of building tech that protects schools, empowers finance teams, and improves education through better systems, KEV is the place for you.

About the Role

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.

How You’ll Contribute

Sales Performance & Forecasting: 

• • 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

Team Leadership & Development: 

• • 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 

Strategic Planning: 

• • 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

Who You Are

• 8+ years of progressive sales experience, including experience working in the K-12 sector
• 3+ years of sales leadership experience with 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 - 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 frequently 

What We Offer

• 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.