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About the Role
This is a consultative, data-driven role that requires comfort working across multiple decision-makers and leveraging AI-powered insights to prioritize and personalize engagement. You’ll manage the full sales cycle for commercial clients, from prospecting and discovery/needs assessment to proposal, contract negotiation, and close.
Responsibilities
- 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.
- Act as a continuous learner who thrives in high-growth, fast-changing, AI-enabled environments.
Requirements
- 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).
- 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.
- 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 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.
Skills
- AI-powered insights
- Sales cycle management
- Prospecting
- Discovery
- Needs assessment
- Proposal generation
- Contract negotiation
- Relationship building
- Stakeholder management
- Automation
- CRM software proficiency (Salesforce, HubSpot, Apollo, LinkedIn Sales Navigator)
- Cold outreach methods (LinkedIn, Email, Cold Calling)
- Inbound and outbound sales strategies
- Independent work
- Time management
- Task prioritization
- Business acumen
- Presentation skills
- Negotiation skills
Location
- Toronto
- North America
Work Type
- Hybrid
- Remote
- In-office
Experience Level
- 3-5 years of B2B sales experience
- Enterprise sales experience
- Mid-market sales experience
Education Level
- Post-secondary education
Salary/Compensations
- $66,000 to $78,000
Benefits
- Participation in Company Profit Sharing Program of up to 8% of base salary
- Eligibility for Sales Incentive/Bonus Program
- Comprehensive Extended Health and Dental Benefits
- Generous Paid Time Off, including annual vacation and personal days
- Hybrid Work Environment
- Professional Development Opportunities
- Access to Health and Wellness Programs, including gym facilities
About the Company
- O2E Brands has been voted one of the Best Workplaces in Canada 14 times.
- We know that great talent comes in many forms, and we want to meet you at your best.
- We value diversity and inclusivity.
- We provide reasonable accommodations to applicants with disabilities at any time throughout the recruitment and selection process upon request.
- Brands include: 1800GOTJUNK.COM, WOW1DAY.COM, SHACKSHINE.COM
Equal Opportunity
- We value diversity and inclusivity.
- We will provide reasonable accommodations to applicants with disabilities at any time throughout the recruitment and selection process upon request.