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

Entrata entrata.com Open
Remote Toronto Full-time VP Sales Leadership

At a glance

VP-level Sales Leadership role at Entrata. Remote, Canada · full-time · CA$145,000–CA$187,000 base.

SalaryStated by Entrata
CA$145,000 – CA$187,000
Base salary for this role, in CAD per year, as published in the posting.
This role, from EntrataOur estimate for the market: CA$134,650–CA$192,750Median CA$166,000
The range includes the market median of CA$166,000 for lead sales leadership roles in Toronto, compared against the Toronto market.
Worked out from 19 postings that stated pay, median CA$166,000. Last updated Oct 29, 2026.
RoleSales Leadership
SeniorityVP
LocationToronto
WorkplaceRemote
EmploymentFull-time
Base payCA$145,000–CA$187,000
PostedSep 10, 2026
Role brief

growthroles summary, based on the employer's posting.

What you'll do

  • Win new commercial accounts across Canada, from finding prospects through turning them into customers
  • Present solutions to prospects, address their questions, and negotiate pricing and contract terms
  • Set regional sales direction, lead account strategies, and coach teammates toward performance goals
  • Review regional results to spot growth opportunities and shape corrective sales initiatives
  • Travel domestically for prospect meetings, industry events, and company gatherings

What you bring

  • At least eight years selling technology or software, with enterprise sales results you can demonstrate
  • A bachelor's degree and a record of beating sales goals while growing strategic accounts
  • Experience building and carrying out sales plans for a region or department

Who this fits

This is an independent, senior enterprise sales role with responsibility for guiding teammates, not a people-management title. The role is remote in Toronto and requires domestic travel for business meetings and events.

From the employer

Since 2003, Entrata has evolved from a visionary, student-led startup into a global leader in AI-driven property management technology. Today, we power the industry's most essential operating system, serving owners and residents worldwide through a comprehensive suite of intelligent leasing, payment, and communication tools powered by cutting-edge AI. With a proven track record of sustained growth and a global team of more than 2,200 employees, we offer the rare combination of established stability and high-velocity innovation. Recognized by the Silicon Slopes Hall of Fame and the Utah Business Fast 50, Entrata fosters a culture of radical transparency and entrepreneurial energy. At Entrata, we create an environment where different perspectives are valued and respected. Those perspectives challenge assumptions, strengthen our decisions, and raise the bar as we reshape the global living experience through AI-powered solutions.

Drives regional growth through the acquisition of new commercial customer accounts. Applies advanced knowledge of products, market trends, and prospect needs to develop innovative solutions.

Duties/Responsibilities

  • Identifying prospective commercial customers, generating leads, and converting them into clients.

  • Contacting new commercial customers to discuss their needs.

  • Emphasizing product features to showcase how they address prospects' challenges.

  • Answering prospect inquiries about our products.

  • Negotiating prices and terms and preparing sales agreements.

  • Collaborating with colleagues across various sectors.

  • Maintaining contact lists and nurturing prospect relationships through follow-ups.

Essential Functions

  • Lead regional commercial account initiatives to achieve significant revenue growth.

  • Conduct high-level prospective client presentations, negotiations, and strategy sessions independently.

  • Guide and support team members in executing new account strategies and achieving performance targets.

  • Analyze regional performance metrics to identify opportunities for improvement and drive strategic initiatives.

  • Travels domestically for prospect meetings, industry events, and company gatherings as required to maintain business relationships and achieve objectives.

  • Ability to prioritize tasks effectively by meeting deadlines and managing workload efficiently.

  • Maintain professional interactions with internal and external stakeholders

  • Ability to work in a fast-paced and high-stress environment

Minimum Qualifications/Skills

  • Proven success in enterprise technology or software sales (SaaS, PaaS, etc.) with measurable results.

  • Strong strategic thinking and problem-solving abilities, with the capacity to manage complex prospect relationships.

  • Demonstrated leadership skills, including mentoring and guiding less experienced team members.

  • Excellent communication and influence skills with the ability to align diverse stakeholders around business objectives.

  • Ability to work independently while leading cross-functional initiatives.

Education and Experience Requirements

  • Bachelor’s degree required; advanced degree preferred.

  • Minimum of 8 years of experience in technology or software sales, preferably 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.

AI & Operational Fluency

  • AI Integration: Utilize company-approved GenAI tools to accelerate high-value deliverables.

  • Strategic Oversight: Exercise critical judgment as the "Human-in-the-Loop," by auditing AI outputs for factual accuracy, brand alignment, and the removal of hallucinations.

  • Data Governance: Ensures no proprietary or Personally Identifiable Information (PII) data is exposed to unauthorized models.

  • Prompt Competency: Demonstrates the ability to craft clear, context-rich prompts to achieve consistent, high-quality results across various business domains.

Benefits:Flexible and transparent culture with remote and hybrid work options, generous vacation time, and frequent company recharge days for work-life balance.
Comprehensive medical, dental, and vision coverage, including fertility benefits, available for eligible employees and their families.
HSA/FSA options and employer-paid disability benefits provided for eligible employees.
Access to 401(k) or similar retirement plans with employer matching for eligible employees, ensuring long-term financial security.
Wellness initiatives promoting physical and mental well-being, access to an onsite gym at HQ, gym memberships, mental health resources, wellness challenges, and employee assistance programs.
Entrata Cares programs offers opportunities for volunteerism, charity events, and giving back to our community.
Exclusive Previ cell phone plan and discounts on services or local business partnerships for additional employee benefits.
Bi-annual swag drops for employees
Currently, Entrata hires in Arizona, Idaho, Utah, Wyoming, Texas, North Carolina, Florida, Georgia, South Carolina, Ohio, Pennsylvania, and Illinois for Exempt roles and Arizona, Idaho, Utah, Wyoming, Texas, North Carolina, and Florida for Non-Exempt roles.
Entrata is dedicated to creating a workplace where a diverse and inclusive team thrives in an environment free from discrimination. We provide equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, protected veteran status, or any other applicable characteristics protected by law.
It’s a great place to work! Will you join us?
Opportunity

Sales Leadership work from LinkedIn, X, Reddit and Upwork, in one list.

Each morning you get everything that fits, strongest first.

Sales LeadershipRemote

Find me work

By the team behind growthroles.

Find me work
Opportunity

Sales Leadership work from LinkedIn, X, Reddit and Upwork, in one list.

Each morning you get everything that fits, strongest first.

Find me work

By the team behind growthroles.