Enterprise Account Executive – New Business

Are you a SaaS based sales hunting professional looking to join an expanding company in the Toronto market? Osborne is delighted to partner with an innovative company that provides public and private sector organizations with crucial access to workplace data across their existing tech stack. After tremendous success and growth abroad, the Canadian market has grown significantly and offers endless growth potential.

Are you an individual who wants to have their handprints on continuing to scale and grow the business? This is a hunter role—not account management. We want someone who lives for and loves winning new business.

Key Responsibilities:

Own the full sales cycle from prospecting and discovery through to signed contract.

Build your own pipeline through targeted outbound activity, networking, referrals and your existing relationships.

Conduct detailed conversations with business leaders, HR, technology, real estate facilities and Human Resources.

Present and lead stellar presentations specifically focused on client’s product and technical specialists to secure buy-in from decision makers.

Navigate multiple stakeholders and enterprise buying processes, including procurement, IT, information security and legal.

Develop and present proposals, pricing and commercial recommendations.

Maintain opportunities and manage pipelines through HubSpot.

Collaborating with the CEO, COO, Canadian partner, production and technical teams.

Contribute to the continued development of the Canadian go-to-market strategy as the business grows.

Qualifications & Experience:

A minimum of 5 years' B2B technology sales experience, with a strong focus on current business.

A history of over-achieving,



and exceeding sales quotas.

Extensive full-cycle sales experience, from prospecting, needs analysis, developing proposals, negotiating and contract confirmation and signing.

The ability to demonstrate a genuine commitment to a defined sales process,

including discovery, qualification and advancing opportunities.

Experience selling technology solutions to multiple stakeholders within mid-market or enterprise organizations.

The drive and ability to generate your own pipeline of opportunities as well as business development-generated opportunities.

Strong commercial judgement and the persistence to maintain momentum through longer sales cycles.

Experience working with a CRM such as HubSpot or Salesforce.

Experience or understanding of workplace technology, PropTech, corporate real estate, workplace analytics or occupancy technology would be an asset but is not essential.

Extensive experience in full-cycle new business technology sales.

Salary: $80,000 - $100,00

Competitive benefits and perks

Osborne Recruitment is an equal opportunity employer committed to supporting an inclusive and accessible environment. Should you require accommodation or support in any aspect of the recruitment and selection process, we will assist to meet your needs.

This posting is for an existing vacancy.

Osborne does at times employ certain artificial intelligence (AI) technologies to enhance our recruitment processes. All AI-assisted evaluations are reviewed by our recruitment professionals to ensure fairness and accuracy and do not make autonomous hiring decisions. Final decisions rest with our human recruitment team, ensuring a balanced and fair evaluation process.

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📌 Enterprise Account Executive - New Business (Manitoba)
🏢 Osborne Recruitment
📍 Manitoba