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Key skills for this role
Own the full sales cycle for mid-market and enterprise accounts, from prospecting and discovery to a signed agreement.
Build and maintain strong relationships across multiple stakeholders, including Operations, Finance, and Legal.
Use automation and AI to streamline outreach, follow-ups, and proposal generation.
Maintain accurate pipeline forecasting, deal progression, and opportunity data within CRM.
Partner with Operations and Account Management to ensure seamless onboarding and handoff of new clients.
Identify whitespace and cross-sell opportunities within key verticals such as Retail, Property Management, Construction, and Restaurant Chains.
Represent the organization at major national conferences and trade events to build pipeline and brand visibility.
Share learnings with leadership and RevOps to continuously optimize sales processes and messaging.
Demonstrate success in multi-threading complex sales cycles engaging multiple stakeholders and navigating enterprise decision processes.
Land and expand Enterprise Accounts , ideally in B2B service-based or multi-location industries.
A continuous learner who thrives in high-growth, fast-changing, AI-enabled environments.
3–5 years of B2B sales experience, preferably within multi-site or enterprise environments across various industries, especially Retail and Property Management.
Must be located in the GTA (Greater Toronto Area)
Post-secondary education - required
Ability to travel across North America for conferences and client meetings (50% travel).
Proficiency in using smart prospecting and CRM software (e.g., Salesforce, HubSpot, Apollo, LinkedIn Sales Navigator, etc.) to manage outreach campaigns effectively.
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Proficiency in driving results through various cold outreach methods, including LinkedIn, Email communications, and cold calling.
Demonstrated success in managing inbound and outbound sales strategies to generate leads and drive revenue growth.
Prior experience managing long and complex sales cycles.
Proven ability to work independently, manage time efficiently, and prioritize tasks in a fast-paced environment.
Prior experience selling to C-Suite and VPs at enterprise corporations
Ability to build trust quickly and establish long-lasting relationships with both our customers and internal stakeholders
Strong desire and passion to succeed in sales & achieve results.
Strong communication skills with the ability to articulate value propositions.
A passion for personal and professional growth.
Strong business acumen, presentation, and negotiation skills.
Background in retail, facilities management, or property management is an asset.
If you love BOTH the journey and the destination, this job may be for you, so let’s connect!
New business revenue generated (target: $X annualized).
Conversion rate from qualified opportunity → closed deal.
Average deal size and time-to-close.
Customer satisfaction and retention post-handoff.
Pre-Screen – Let’s talk about your experience, goals & excitement for this role!
Interviews – Two or more interviews with different team members, including structured competency & scenario-based questions
Presentation/Assessment
References & Background Check
We use audio recording transcription for our interview practices
Canadian home-services franchisor helping entrepreneurs build junk removal, painting, and home-maintenance businesses.
Visit company websiteJobs and hiring trendsCAD 66000-78000 yearly / year
Full-time
Mid · 3+ years experience
Hybrid
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