Head of Sales (Remote from Canada)

Jobgether; Remote; CAD 100,000 - 150,000; Full time

Job summary

A fast-growing technology company in Canada is looking for a Head of Sales to lead the strategic sales vision. You will oversee the full sales cycle, manage a high-performing team, and implement strategies that drive revenue growth and expand market reach. Ideal candidates have 7+ years of sales experience, strong technical aptitude, and the ability to thrive in dynamic environments. This role offers a competitive compensation package along with flexibility to work remotely or from the office.

Benefits

Competitive compensation package

Medical, dental, vision, and mental health insurance

Flexible PTO

Learning and development allowance

Paid parental leave

Qualifications

• 7+ years of successful sales experience with a consistent record of exceeding quotas, ideally in B2B technology.
• Demonstrated experience managing or leading high-performing sales teams.
• Ability to thrive in a fast-paced startup environment and operate autonomously.

Responsibilities

• Develop and implement a strategic sales plan to drive revenue growth.
• Lead, mentor, and inspire a high-performing sales team.
• Manage the full sales cycle, including qualification, evaluation, and negotiation.

Skills

Sales experience

Technical aptitude

Communication skills

Negotiation skills

Strategic planning

Job description

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.

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