Director, Sales

Director Of Sales

About KEV : KEV Group is an enterprise SaaS company that provides an all-in-one activity fund management solution for K-12 schools. By seamlessly integrating and automating all fee management processes, our SchoolCash platform provides real-time visibility and control over how districts and schools create, collect, manage, track, and reconcile these funds. Parents benefit from an easy-to-use solution that offers convenience and supports all payment types. More than 26,000 schools across North America rely on our solutions to manage over $4 billion in activity funds annually. The company is headquartered in Toronto with offices in Cambridge, ON and across the U.S., KEV is a portfolio company of Five Arrows. With over 10 billion of assets under management (AUM), the corporate private equity business of Five Arrows invests in companies with highly defensible market positions, strong management teams, and growth-based business models.

Why Join KEV? Work in an industry that benefits children, parents and schools Do meaningful and purpose-driven work, and make a real impact Join a quickly growing organization with real opportunity for learning and growth Passionate and accessible leadership team that cares about people, personally and professionally

Job Description

As we continue to grow, we are looking for an exceptional 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 leaderyou'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.

Responsibilities

• 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

Skills and Experience : 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 mindsetequal 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

We Offer : Competitive salary Comprehensive health and dental benefits Professional development opportunities Continuing Education Great colleagues and collaboration

This job description indicates the general nature and level of work expected. It is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities required by an individual joining the KEV team in this or any other capacity.

KEV Group is pleased to accommodate individual needs in accordance with the Accessibility of Ontarians with Disabilities Act, 2005 (AODA), within our recruitment process. If you require accommodation at any time throughout the recruitment process, please speak with Human Resources or the hiring manager.

KEV Group is an equal opportunity employer who agrees not to discriminate against any employee or job applicant because of race, color, religion, national origin, sex, physical or mental disability, or age.