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Regional Vice President of Sales, Canada (IC-Enterprise)

Entrata - Toronto, ON, Canada - Hybrid - posted 2026-09-10

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Entrata, a global leader in AI-driven property management technology since 2003, is seeking a Regional Vice President of Sales for Canada to drive enterprise commercial customer acquisition and regional revenue growth. In this role, you will lead regional commercial account initiatives to achieve significant revenue targets. You will conduct high-level prospective client presentations, negotiations, and strategy sessions independently, while guiding and supporting team members in executing new account strategies and achieving performance targets. You will identify prospective commercial customers, generate leads, and convert them into clients through consultative selling that emphasizes how Entrata's AI-powered leasing, payment, and communication tools address their specific challenges. Key responsibilities include: - Identifying and converting prospective commercial customers into clients - Contacting new prospects to understand their needs and pain points - Conducting independent high-level presentations and negotiations - Guiding team members in executing regional sales strategies - Analyzing regional performance metrics to identify improvement opportunities - Maintaining prospect relationships and nurturing leads through follow-ups - Collaborating across cross-functional teams to optimize account performance - Traveling domestically for prospect meetings, industry events, and company gatherings - Utilizing company-approved GenAI tools to accelerate deliverables while maintaining data governance and brand alignment Entrata offers a flexible, transparent culture with hybrid work options, generous vacation time, comprehensive medical/dental/vision coverage, 401(k) matching, wellness programs, and opportunities for community involvement through the Entrata Cares program. REQUIREMENTS: - Bachelor's degree required; advanced degree preferred - Minimum 8 years of experience in technology or software sales (SaaS, PaaS, etc.) - Proven success in enterprise technology sales with measurable results - Preferably experience in the multifamily housing industry - Consistent track record of exceeding sales targets and driving strategic account growth - Experience developing and executing regional or departmental sales strategies - Strong strategic thinking and problem-solving abilities with capacity to manage complex prospect relationships - Demonstrated leadership skills, including mentoring and guiding less experienced team members - Excellent communication and influence skills with ability to align diverse stakeholders - Ability to work independently while leading cross-functional initiatives - Ability to prioritize tasks, meet deadlines, and manage workload efficiently in a fast-paced, high-stress environment

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