Head of Sales

This is a fully remote position, open to applicants in Canada.

📋 Description

• Lead, mentor, and develop Sales Team Leads along with their distributed teams across various locations and time zones.

• Define and implement the commercial strategy across multiple brands, focusing on both customer expansion and acquiring new customers.

• Identify, assess, and pursue new market opportunities, customer segments, partnerships, and revenue streams.

• Develop and test scalable go-to-market strategies, prospecting tactics, and sales initiatives that foster sustainable growth.

• Collaborate closely with Marketing to synchronize demand generation, content, campaigns, lead nurturing, and pipeline development efforts.

• Construct and enhance sales processes, playbooks, documentation, scripts, and enablement programs to improve consistency and scalability.

• Establish KPIs, forecasting methods, and performance metrics to promote accountability and informed decision-making.

• Work in conjunction with Customer Success and Account Management teams to maximize customer lifetime value and product utilization.

• Delegate ownership and execution tasks to Team Leads while retaining visibility into performance, priorities, and outcomes.

• Promote alignment across teams through regular business reviews, performance discussions, and follow-ups on key initiatives.

• Analyze market trends, customer insights, and sales performance to continuously refine strategies and execution.

• Act as a hands-on leader who can contribute to strategic initiatives while empowering teams to operate independently.

• Assist with other tasks or projects as assigned to meet team and business objectives.

⛳️ Requirements

• Over 8 years of sales experience, including leadership roles within technology, SaaS, hosting, cloud, digital services, or related fields.

• Proven success in developing and executing sales strategies that generate new business while increasing revenue within existing accounts.

• Experience managing distributed sales teams across different geographies and time zones.

• Strong understanding of outbound sales, prospecting, pipeline development, lead generation, customer acquisition, and account growth strategies.

• Proven experience in identifying and cultivating new market opportunities, customer segments, partner channels, or go-to-market strategies.

• Demonstrated capability to build scalable sales processes, playbooks, frameworks, and performance management systems.

• Experience collaborating closely with Marketing on demand generation, content strategy, lead nurturing, campaign execution, and revenue growth initiatives.

• Strong commercial insight with the ability to recognize opportunities, prioritize initiatives, and execute effectively.

• Comfortable balancing strategic leadership with hands-on execution.

• Familiarity with CRM platforms such as Zoho CRM, Salesforce, HubSpot, or similar tools.

• Strong analytical abilities to leverage data for decision-making, performance improvement, and forecasting results.

• Excellent communication, coaching, and stakeholder management skills.

• Self-driven, entrepreneurial, and highly motivated, with a passion for building and scaling successful sales organizations.

• Experience in the web hosting, cloud services, digital infrastructure, or related technology sectors is highly preferred.

🏝️ Benefits

• Work from anywhere - this is a remote opportunity.

• A competitive salary that recognizes your unique skills and contributions.

• Opportunities for career advancement and professional development to help you achieve your full potential.

• Flexible work arrangements to support a healthy work/life balance.