Director of Sales

Jumpfactor; Toronto; Remote; CAD 120,000 - 160,000; Full time

Job summary

A leading digital marketing agency in Toronto is seeking a Director of Sales to lead their Account Executive and Business Development Representative teams. The successful candidate will drive sales strategy, manage a team, and achieve significant revenue growth. This full-time remote role values strategic leadership and a passion for digital marketing. Competitive compensation and performance-based bonuses are offered.

Benefits

Competitive compensation package

Performance-based bonuses

Access to paid training and conferences

Paid social events

Qualifications

• 5+ years of experience in a Director, Head of Sales, or Senior Sales Leadership role.
• Proven success leading remote B2B sales teams to achieve $5M+ in annual revenue.
• Strong background in digital marketing, SaaS, or IT services is a major advantage.

Responsibilities

• Own and drive sales team performance across pipeline stages.
• Train, coach, and mentor AEs and BDRs to improve conversion and close rates.
• Collaborate with marketing on targeting, campaigns, and qualification criteria.

Skills

Remote sales leadership

Digital marketing knowledge

Consultative selling

Data-driven management

KPI management

Mentoring and coaching

Job description

Overview

Jumpfactor is an award-winning, 8-time Growth500 Fastest Growing Agency in Canada. We are a dynamic, fast-paced, and highly specialized digital marketing agency focused on helping Managed Service Providers (MSPs) and B2B tech companies achieve massive growth. With over $1.6 Billion in client revenue generated, we are recognized globally as a top-tier MSP growth expert. As we scale toward our $50M vision, Jumpfactor is evolving from a traditional agency model into a full-scale hybrid platform combining media, services, and proprietary technology. Our high-performance culture values strategy, tenacity, and radical accountability—making this a unique opportunity to lead sales in a fast-moving, high-growth B2B ecosystem.

ROLE OVERVIEW:

As the Director of Sales, you will take full ownership of Jumpfactor’s Account Executive (AE) and Business Development Representative (BDR) teams, driving sales strategy and pipeline growth. Working directly with executive leadership and marketing, you will refine systems, boost win rates, and build a best-in-class sales organization.

You will be responsible for leading, training, and managing a team of 10+ (5+ AEs and 5+ BDRs), with a clear mandate: close $140K+ in new MRR per month and scale to $200K+ by Q3. This position requires a strategic and tactical leader who can implement systems, mentor high-performing closers, and own the full sales funnel.

Jumpfactor's CORE VALUES:

Be STRATEGIC

Be PASSIONATE

Be TENACIOUS

Maintain INTEGRITY

WHY EMPLOYEES LOVE JUMPFACTOR:

• Very competitive compensation package.
• You will work with a very skilled international team.
• Endless growth opportunities and career advancement.
• Performance-based bonuses that recognize your impact.
• Access to paid training, courses, events, and conferences.
• Enjoy paid social events that foster team camaraderie.
• Engage in weekly learning programs to stay ahead.
• Harness state-of-the-art technologies and tools for excellence.

WHO YOU ARE:

• 5+ years of experience in a Director, Head of Sales, or Senior Sales Leadership role
• Proven success leading remote B2B sales teams to achieve $5M+ in annual revenue
• Strong background in digital marketing, SaaS, or IT services is a major advantage.
• Deep understanding of consultative selling for SMB and mid-market buyers.
• Experienced with mid-ticket packages ($3K–$10K MRR).
• Data-driven operator skilled at managing KPIs and coaching on key sales levers.
• Experienced in building repeatable systems and scaling sales processes.
• Thrives in fast-paced, lean environments while maintaining accountability and empathy.

ROLES AND RESPONSIBILITIES:

• Own and drive sales team performance across pipeline stages.
• Train, coach, and mentor AEs and BDRs to improve conversion and close rates.
• Participate in hiring, onboarding, and performance reviews for all sales hires.
• Establish weekly, monthly, and quarterly sales targets aligned to company goals.
• Build a high-performance culture rooted in accountability, empathy, and results.
• Sales Strategy & Process Development: Refine and implement sales processes for high-ticket and mid-tier offerings.
• Build accurate forecasting and commission tracking with RevOps support.
• Collaborate with marketing on targeting, campaigns, and qualification criteria.
• Provide detailed sales reporting and strategic recommendations to leadership.
• Revenue Growth & Scaling: Lead the team to achieve $140K+ new MRR monthly, scaling to $200K+.
• Ensure CAC efficiency while improving sales velocity and win rates.
• Drive expansion into new market segments while improving close ratios.

NEXT STEPS:

If you are excited about this opportunity and possess the necessary qualifications, we invite you to apply. Successful candidates will undergo a series of assessments to further evaluate their potential.

Job Type: Full-time, Permanent, 100% Remote (EST collaboration required)