Head of Sales (Remote from Canada)

Medium; Remote; CAD 150,000 - 200,000; Full time

Job summary

A dynamic technology company is seeking a Head of Sales to lead their sales efforts in Canada. The role involves defining and executing a strategic sales vision to accelerate revenue growth and expand market reach. Responsibilities include managing a high-performing sales team, driving enterprise deals, and optimizing sales processes. Ideal candidates will have over seven years of B2B technology sales experience and a strong ability to manage complex sales cycles. This position offers a competitive compensation package and flexible working options.

Benefits

Flexible remote work options

Competitive compensation package

Comprehensive health insurance

Flexible PTO and annual holidays

Paid parental leave

Learning and development allowance

Qualifications

• 7+ years of successful sales experience with a record of exceeding quotas.
• Strong technical aptitude and ability to articulate technical products.
• Demonstrated experience in managing high-performing sales teams.

Responsibilities

• Develop and implement a strategic sales plan to drive revenue growth.
• Lead and mentor a high-performing sales team.
• Manage full sales cycle from qualification to deal closing.

Skills

Sales experience

Technical aptitude

Leadership

Communication

Negotiation

Strategic planning

Job description

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Head of Sales in Canada.

This role is an opportunity to lead the commercial engine of a fast-growing, innovation-driven organization shaping the future of advanced technologies. You will define and execute a strategic sales vision that accelerates revenue growth, strengthens customer relationships, and expands market reach. Working closely with technical and cross-functional leaders, you will oversee the full sales cycle—from qualification to deal execution—while guiding a high-performing team. You will also steer operational improvements, refine forecasting, and contribute to long-term strategic planning. This position is ideal for a sales leader who thrives in dynamic environments, values autonomy, and excels at turning complex products into compelling business outcomes.

Accountabilities

• Develop and implement a strategic sales plan to drive revenue growth and expand the customer base.
• Lead, mentor, and inspire a high-performing sales team to achieve quarterly and annual targets.
• Build and maintain strong relationships with prospective clients, engaging confidently in both technical and business discussions.
• Manage the full sales cycle, including qualification, technical evaluation, pilot-stage account management, negotiation, and deal closing.
• Partner with Solutions Engineers to qualify prospects, ensure successful pilot engagements, and support strategic account expansion.
• Recruit, develop, and elevate sales talent while nurturing a collaborative, results-driven culture.
• Drive enterprise and strategic deals ranging from 100k to 2M+, optimizing processes for greater efficiency.
• Lead and contribute to initiatives that refine the sales process across the organization.
• Use CRM and sales tools to derive insights, improve decision-making, and enhance forecasting accuracy.
• Develop strategies that ensure customer success and support long‑term account growth, including new use cases in collaboration with cross‑functional teams.

Requirements

• 7+ years of successful sales experience with a consistent record of exceeding quotas, ideally within B2B technology or enterprise software.
• Strong technical aptitude and the ability to understand and articulate deeply technical products or solutions.
• Demonstrated experience managing or leading high-performing sales teams.
• Proven ability to manage complex enterprise sales cycles with a consultative and relationship-driven approach.
• Confidence in delivering presentations to diverse audiences, from technical stakeholders to C-level executives.
• Ability to thrive in a fast-paced startup environment, operate autonomously, and adapt to evolving structures.
• Strong communication, negotiation, and strategic planning skills.

Benefits

• Flexibility to work remotely or from an office in the San Francisco Bay Area.
• Competitive compensation package.
• Medical, dental, vision, and mental health insurance, along with life and long-term disability coverage.
• Non-matching 401(k) plan.
• Flexible PTO, winter shutdown, and 11 annual holidays.
• Eight weeks of paid parental leave.
• New hire equipment and accessories budget for an optimal setup.
• Annual learning and development allowance.

Why Apply Through Jobgether?

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.