Director of Sales in Canada Creek, Nova Scotia at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director of Sales based in Canada.

This is a senior commercial leadership opportunity for an experienced sales leader ready to shape and scale a growing North American organization. Reporting directly to executive leadership, you will oversee quota-carrying sales representatives, business development, and sales leadership functions. The role combines hands-on deal involvement with strategic ownership of sales performance, forecasting, territories, and go-to-market execution. You will coach and develop a high-performing team while building repeatable processes that support consistent growth. You will also cultivate relationships with senior decision-makers across commercial real estate and multi-site organizations. With a direct seat at the leadership table, you will play a central role in supporting expansion into new markets.

• Lead, coach, and develop the full sales organization, including sales team leadership, quota-carrying representatives, and outreach/business development teams.
• Own monthly, semi-annual, and annual net-new and renewal objectives and maintain accountability for achieving team targets.
• Establish and manage a consistent sales cadence through pipeline reviews, deal coaching, forecasting sessions, and one-on-one meetings.
• Set individual targets, territory assignments, activity standards, and performance expectations while supporting team members in achieving their goals.
• Recruit, onboard, and ramp new sales talent as the organization expands across North America.
• Build a culture centered on accountability, collaboration, optimism, and continuous development.
• Maintain accurate, fully staged pipelines and strong CRM discipline, using HubSpot or an equivalent platform.
• Deliver reliable weekly and monthly forecasts to executive leadership and use sales data to identify trends and opportunities for improvement.
• Analyze conversion rates, sales-cycle length, win/loss performance, and representative productivity to inform commercial decisions.
• Ensure inbound leads are appropriately routed, followed up on, and progressed within defined service levels.
• Co-develop and execute the annual sales strategy with executive, marketing, and technology stakeholders, including targets, territories, segment priorities, and enablement plans.
• Own and continuously improve sales playbooks, team guides, and upsell and renewal processes.
• Develop strong expertise in commercial real estate and multi-site, portfolio-level sales involving asset owners and property managers.
• Drive expansion into new North American markets in alignment with broader growth priorities.
• Step into strategic and complex opportunities as an executive sponsor, negotiator, and closer.
• Build relationships with senior decision-makers across large commercial real estate portfolios and strategic accounts.
• Represent the organization at industry conferences, networking events, and client meetings across North America.
• Monitor market trends, competitors, and industry developments and translate relevant insights into sales strategy and team execution.

Requirements:

• At least 5 years of B2B sales experience, including at least 3 years of experience leading and managing a quota-carrying sales team.
• Proven track record of building and scaling sales teams that consistently meet or exceed revenue targets.
• Experience selling multi-year, subscription-based, or recurring-revenue services to enterprise or commercial real estate clients is a strong asset.
• Bachelor’s degree in sales, business, or a related field.
• Fluency in written and spoken English; French proficiency is a strong asset.
• Advanced experience with HubSpot, particularly pipeline management, reporting, and forecasting, or demonstrated mastery of an equivalent CRM.
• Strong analytical capabilities, with the ability to build forecasts, interpret dashboards, evaluate sales performance, and make data-informed decisions.
• Exceptional communication skills across listening, presentation, writing, and executive-level communication.
• Ability to communicate clearly and effectively with both early-career sales representatives and C-level clients.
• Strong coaching and people-leadership skills, with the ability to foster collaboration, maintain team spirit, and conduct direct and constructive performance conversations.
• Self-starter mentality with a high level of reliability, motivation, ownership, and comfort operating autonomously in a fast-growing environment.
• Resilience and an optimistic, solutions-oriented approach to the challenges and fluctuations of complex sales cycles.
• Adaptability and willingness to contribute hands-on across multiple commercial functions when needed.
• Ability and willingness to travel across North America for client meetings, team ride-alongs, networking opportunities, and industry events.

Benefits:

• Base salary of $120,000 per year.
• Commission based on overall team performance, with additional earning potential for exceeding team targets.
• Mostly remote work arrangement with regular travel for client meetings, team ride-alongs, networking events, and industry activities.
• Career development opportunities within a fast-growing organization with an international expansion plan.
• Dynamic team culture, including team BBQs and access to fresh produce from local farming operations when based near a hub or visiting local teams.
• Direct exposure to executive leadership and a seat at the leadership table.
• Opportunity to contribute to North American growth and future market expansion.