Director of Sales

Key Responsibilities Strategic Market Development & Growth * Develop and execute a strategic business development plan targeting Canadian K-12 school boards, with a focus on Alberta and British Columbia ERP modernization opportunities. * Identify, evaluate, and prioritize new market opportunities including untapped regions, consortium agreements, and strategic partnerships. * Build and maintain a qualified pipeline from initial engagement through contract execution, with a focus on multi-year, enterprise-level deals. * Lead end-to-end enterprise sales cycles: discovery, solution positioning, proposal development, RFP/RFQ response, and contract negotiation. * Monitor market trends, policy changes, funding models, and competitive activity to inform go-to-market strategy. Client & Partner Relationship Management * Develop and nurture strategic relationships with school board executives, business officers, IT leaders, and key decision-makers. * Act as a trusted advisor, aligning SDS solutions to each prospect's strategic priorities (finance, HR, payroll, compliance, modernization). * Leverage existing SDS school board partnerships for reference opportunities, case studies, and expansion. * Identify and cultivate strategic alliances (complementary technology providers, consulting partners, associations) that extend SDS's market reach. Sales Strategy, Enablement & Collaboration * Collaborate with Product, Marketing, and Customer Success to refine value propositions, messaging, and sales collateral for the K-12 market. * Provide structured market feedback on product gaps, pricing, and competitive positioning to inform roadmap decisions. * Lead the development of standardized sales playbooks, proposal templates, and enterprise engagement best practices for the SDS sales function. * Represent SDS at industry events, conferences, and association meetings across Canada. AI Strategy & Adoption * Own the AI-enabled sales strategy for SDS: Define, implement, and continuously improve the AI-powered tools, workflows, and methodologies that underpin the SDS sales function's scalability and efficiency. * Establish the AI sales technology stack: Evaluate, select, and deploy AI-enhanced CRM capabilities, predictive analytics, lead-scoring models, and opportunity intelligence tools — setting the standard for current and future SDS sales team members. * Leverage generative AI as a force multiplier: Use tools such as Copilot, Claude, and other generative AI platforms to draft and refine proposals, RFP responses, presentations, and tailored client communications — establishing templates and prompt libraries that scale beyond the individual. * Drive AI-powered market and competitive intelligence: Implement AI-enabled platforms to systematically monitor competitor activity, pricing trends, policy changes, and key stakeholder movements across the K-12 sector — converting raw intelligence into actionable go-to-market decisions. * Embed AI into pipeline management and forecasting: Use AI-driven analytics to forecast revenue, segment markets, analyze win/loss patterns, and improve conversion rates — ensuring data-driven decision-making is the SDS sales standard, not the exception. * Collaborate with Marketing on AI-assisted demand generation: Partner with Marketing to design AI-powered campaigns, personalized outreach sequences, and nurture journeys that drive qualified pipeline at scale. * Champion AI adoption across the broader organization: Mentor Sales, BD, and adjacent team members on AI-driven workflows and best practices. As the team scales, establish AI proficiency expectations for all new hires and integrate AI competency into onboarding and performance management. * Continuously evaluate emerging AI tools: Maintain an active technology scouting practice to identify and pilot new AI solutions that reduce administrative overhead and maximize direct selling time. Internal Leadership & Continuous Improvement * Lead sales forecasting, pipeline reviews, and executive reporting with rigorous data accuracy and clear visibility into growth opportunities. * Mentor and coach members of the Sales and Business Development team by sharing best practices, deal strategies, and AI-driven workflows. * Drive cross-functional initiatives across the customer lifecycle — from initial engagement through implementation and long-term partnership. * Maintain complete documentation of interactions, opportunities, and outcomes in the CRM and systems of record. * As the SDS business scales, build and lead the SDS sales team — including hiring, performance management, quota allocation, and team development. Salary range: $115,000 - $125,000 CAD per year.